471:
704:
38:
940:
29:
1825:
699:
Rimantadine is bound inside the pore to amantadine specific amino acid binding sites with hydrogen binding and van der Waals interactions. The ammonium group (with neighboring water molecules) is positioned towards the C terminus with the amantadane group is positioned towards the N-terminus when
748:
studies show that there is no significant difference between the R and S enantiomers in binding affinity to amino acids in the M2 channel. Since the enantiomers have similar binding affinity, they also have similar ability to block the channel pore and work as an effective antiviral.
1975:
Rimantadine and related compounds useful as antivirals were first described by
Prichard in U.S. Pat. Nos. 3,352,912 and 3,592,934. Both patents describe the preparation of rimantadine from the corresponding ketone oxime by reduction with lithium aluminum
635:
infection. When taken within one to two days of developing symptoms, rimantadine can shorten the duration and moderate the severity of influenza. Rimantadine can mitigate symptoms, including fever. Both rimantadine and the similar drug
719:
The mutation S31N binding site with rimantadine is shown in the image to the left. It shows rimantadine binding into lumenal (top) or peripheral (bottom) binding sites with influenza M2 channel Serine 31 (gold) or
Asparagine 31 (blue).
947:
1-carboxyadamatanones are reduced with sodium borohydride to create racemic hydroxy acid. Excess methyllithium is then added to create methyl ketones which when reduced with lithium aluminum hydride gives the amine group.
1496:
Singer C, Papapetropoulos S, Gonzalez MA, Roberts EL, Lieberman A (July 2005). "Rimantadine in
Parkinson's disease patients experiencing peripheral adverse effects from amantadine: report of a case series".
1567:
Younossi ZM, Perrillo RP (1999). "The roles of amantadine, rimantadine, ursodeoxycholic acid, and NSAIDs, alone or in combination with alpha interferons, in the treatment of chronic hepatitis C".
752:
Rimantadine enantiomers R and S are pictured interacting with the M2 pore below to the right. This image shows that there is not a significant modeled difference between the R and S enantiomers.
1851:
716:
Resistance to rimantadine can occur as a result of amino acid substitutions at certain locations in the transmembrane region of M2. This prevents binding of the antiviral to the channel.
3044:
3039:
1876:
Camps P, Duque MD, Vázquez S, Naesens L, De Clercq E, Sureda FX, López-Querol M, Camins A, Pallàs M, Prathalingam SR, Kelly JM, Romero V, Ivorra D, Cortés D (December 2008).
772:. However, in general, neither rimantadine nor amantadine is a preferred agent for this therapy and would be reserved for cases of the disease that are less responsive to
1715:
Danysz W, Parsons CG, Kornhuber J, Schmidt WJ, Quack G (July 1997). "Aminoadamantanes as NMDA receptor antagonists and antiparkinsonian agents--preclinical studies".
4823:
1801:"BindingDB BDBM50216627 (alpha-methyl-1-adamantyl)methylamine::1-Adamantan-1-yl-ethylamine::CHEMBL959::RIMANTADINE::US11241393, Rimantadine::rimantadin::rimantidin"
4095:
823:. Approximately 6% of patients (compared to 4% of patients taking a placebo) reported side-effects at a dosage of 200 mg/d. Common side effects include:
1925:
Manchand PS, Cerruti RL, Martin JA, Hill CH, Merrett JH, Keech E, et al. (July 1990). "Synthesis and antiviral activity of metabolites of rimantadine".
125:
3199:
979:, 1967). Prichard's methods of synthesis of rimantadine from the corresponding ketone oxime were based on its reduction with lithium aluminum hydride.
6159:
5919:
4346:
3440:
644:. Rimantadine is found to be more effective than amantadine because when used the patient displays fewer symptoms. Rimantadine was approved by the
5300:
4567:
1193:
Antiviral Agents for the
Treatment and Chemoprophylaxis of Influenza: Recommendations of the Advisory Committee on Immunization Practices (ACIP)
5994:
5889:
5250:
4633:
3633:
1649:
5859:
5686:
4597:
4491:
3839:
2197:
60:
5536:
5495:
5445:
5390:
4381:
4361:
4178:
561:
4623:
2338:
5939:
4643:
4204:
4088:
2261:
3642:
1461:
Evidente VG, Adler CH, Caviness JN, Gwinn-Hardy K (1999). "A pilot study on the motor effects of rimantadine in
Parkinson's disease".
4883:
4325:
4271:
3489:
6106:
6014:
2077:
684:. The M2 channel is known to be responsible for viral replication in the influenza virus. Genetic studies suggest that the virus
6070:
6088:
6079:
4421:
4416:
3595:
1532:
Zlydnikov DM, Kubar OI, Kovaleva TP, Kamforin LE (1981-05-01). "Study of rimantadine in the USSR: a review of the literature".
1117:
Jefferson T, Demicheli V, Di
Pietrantonj C, Rivetti D, et al. (Cochrane Acute Respiratory Infections Group) (April 2006).
888:
Taking anticholinergic drugs with amantadine may increase underlying seizure disorders and aggravate congestive heart failure.
4081:
4024:
3600:
2754:
1035:"Neuraminidase inhibitor-rimantadine combinations exert additive and synergistic anti-influenza virus effects in MDCK cells"
655:
samples tested have shown resistance to rimantadine, and it is no longer recommended to prescribe for treatment of the flu.
1800:
6097:
3836:
3136:
2848:
2810:
2399:
1998:
Zlydnikov DM, Kubar OI, Kovaleva TP, Kamforin LE (1981). "Study of rimantadine in the USSR: a review of the literature".
535:
6169:
3626:
3167:
1177:
606:
3339:
3334:
3141:
2384:
620:
581:
6164:
4041:
3447:
3402:
2771:
1306:"Functional studies indicate amantadine binds to the pore of the influenza A virus M2 proton-selective ion channel"
1204:
Vorobjev YN (April 2020). "An effective molecular blocker of ion channel of M2 protein as anti-influenza A drug".
5479:
4510:
3427:
3034:
3029:
3024:
260:
155:
6154:
6115:
3213:
3111:
3054:
3019:
3014:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
6174:
3619:
2055:
879:(aspirin) while taking rimantadine is known to reduce the body's uptake of rimantadine by approximately 12%.
6061:
3805:
2070:
1654:
645:
362:
3777:
3228:
3146:
3131:
797:
450:
5384:
4485:
733:
2045:
411:
3574:
3189:
820:
1412:
Drakopoulos A, Tzitzoglaki C, Ma C, Freudenberger K, Hoffmann A, Hu Y, et al. (February 2017).
1255:
Drakopoulos A, Tzitzoglaki C, Ma C, Freudenberger K, Hoffmann A, Hu Y, et al. (February 2017).
676:
and blocking proton transport across the M2 channel. Rimantadine is believed to inhibit influenza's
2374:
2040:
1659:
1594:
911:
789:
696:, plays an important role in the susceptibility of influenza A virus to inhibition by rimantadine.
466:
4903:
4029:
3531:
3417:
3387:
3382:
3276:
3081:
2803:
2759:
2511:
2063:
1752:"Amantadine: reappraisal of the timeless diamond-target updates and novel therapeutic potentials"
1680:
Zimmerman RK (March 2007). "Rationing of influenza vaccine during a pandemic: ethical analyses".
1614:
Zimmerman RK (March 2007). "Rationing of influenza vaccine during a pandemic: ethical analyses".
1082:
Zimmerman RK (March 2007). "Rationing of influenza vaccine during a pandemic: ethical analyses".
915:
113:
70:
50:
5289:
4465:
3590:
3392:
3194:
3162:
3097:
2623:
2608:
2394:
2389:
1167:
817:
769:
432:
198:
5635:
4909:
4576:
3667:
3172:
2570:
2565:
2515:
2379:
740:
has a stronger binding affinity to the M2 channel pore than the S-enantiomer of rimantadine.
546:
2050:
959:
Rimantadine was discovered in 1963 and patented in 1965 in the US by
William W. Prichard in
6144:
5884:
5095:
4366:
3851:
3679:
3182:
2369:
1317:
964:
951:
The synthesis pictured to the left is a synthesis of rimantadine as synthesized in Europe.
876:
371:
286:
227:
351:
8:
6024:
4757:
4396:
4199:
3774:
3719:
3242:
3126:
2843:
1192:
277:
1878:"Synthesis and pharmacological evaluation of several ring-contracted amantadine analogs"
1321:
784:
Rimantadine is shown to be effective against other RNA-containing viruses. It can treat
4107:
3374:
3316:
3063:
2833:
2796:
2560:
2465:
2035:
1902:
1877:
1776:
1751:
1438:
1413:
1389:
1364:
1340:
1305:
1281:
1256:
1237:
1143:
1118:
796:. Other viruses that can be treated with Rimantadine include respiratory synctial and
680:, possibly by preventing the uncoating of the virus's protective shells, which are the
470:
92:
1728:
1363:
Wright AK, Batsomboon P, Dai J, Hung I, Zhou HX, Dudley GB, Cross TA (February 2016).
1304:
Jing X, Ma C, Ohigashi Y, Oliveira FA, Jardetzky TS, Pinto LH, Lamb RA (August 2008).
1059:
1034:
5954:
5812:
4104:
3695:
3397:
3326:
2884:
2838:
2721:
2015:
1942:
1907:
1781:
1732:
1697:
1631:
1576:
1549:
1514:
1478:
1474:
1443:
1394:
1345:
1286:
1241:
1229:
1221:
1173:
1148:
1099:
1064:
1050:
923:
745:
673:
652:
422:
170:
84:
703:
5934:
5802:
5410:
5225:
4834:
4667:
4276:
4115:
4064:
3894:
3698:
3539:
3484:
3474:
3412:
3076:
2899:
2894:
2889:
2879:
2580:
2007:
1934:
1897:
1889:
1771:
1763:
1724:
1689:
1623:
1541:
1506:
1470:
1433:
1429:
1425:
1384:
1376:
1335:
1325:
1276:
1272:
1268:
1213:
1138:
1134:
1130:
1091:
1054:
1046:
813:
765:
632:
487:
180:
138:
37:
1693:
1627:
1365:"Differential Binding of Rimantadine Enantiomers to Influenza A M2 Proton Channel"
1217:
1095:
773:
6149:
5485:
5475:
5455:
5325:
5235:
4506:
4456:
3964:
3939:
3919:
3909:
3871:
3512:
3496:
2101:
2097:
843:
729:
551:
311:
220:
208:
188:
1986:
1970:
5787:
5762:
5727:
5651:
5500:
5230:
5190:
4516:
4451:
4073:
4035:
3995:
3808:
3251:
2858:
2765:
2705:
2284:
2089:
1959:
1767:
1310:
Proceedings of the
National Academy of Sciences of the United States of America
677:
628:
2085:
2011:
1893:
1545:
1414:"Affinity of Rimantadine Enantiomers against Influenza A/M2 Protein Revisited"
1257:"Affinity of Rimantadine Enantiomers against Influenza A/M2 Protein Revisited"
975:
969:
6138:
5999:
5914:
5874:
5747:
5566:
5490:
5450:
5430:
5330:
5075:
4924:
4919:
4862:
4813:
4742:
4547:
4309:
4245:
3709:
3611:
3544:
3407:
2298:
1225:
919:
793:
216:
1330:
1021:
20:
6009:
6004:
5989:
5909:
5869:
5843:
5838:
5797:
5792:
5641:
5586:
5576:
5541:
5531:
5460:
5420:
5380:
5340:
5315:
5305:
5295:
5245:
5220:
5215:
5185:
5140:
4944:
4939:
4899:
4752:
4582:
4562:
4552:
4496:
4481:
4471:
4386:
3949:
3934:
3879:
3655:
3646:
3554:
3177:
2853:
2680:
2675:
2645:
2619:
2604:
2594:
2431:
2353:
2251:
2202:
2172:
2093:
1911:
1785:
1701:
1635:
1580:
1518:
1482:
1447:
1398:
1349:
1290:
1233:
1152:
1103:
1068:
1003:
589:
InChI=1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
133:
2019:
1946:
1736:
1553:
939:
5974:
5959:
5944:
5807:
5777:
5772:
5767:
5737:
5711:
5706:
5701:
5676:
5671:
5656:
5646:
5626:
5621:
5606:
5596:
5591:
5581:
5561:
5546:
5526:
5511:
5465:
5400:
5375:
5365:
5360:
5355:
5310:
5285:
5255:
5205:
5165:
5110:
5105:
5085:
5050:
5035:
5025:
5015:
4995:
4985:
4929:
4844:
4767:
4762:
4747:
4607:
4602:
4592:
4557:
4532:
4501:
4461:
4341:
4286:
4260:
4250:
4189:
3969:
3954:
3944:
3847:
3749:
3739:
3714:
3559:
3286:
3281:
3071:
2726:
2700:
2695:
2655:
2650:
2614:
2599:
2589:
2534:
2520:
2440:
2421:
2413:
2271:
2226:
2221:
2167:
2162:
2157:
2152:
2132:
2110:
1380:
872:
801:
689:
78:
1938:
331:
5979:
5969:
5964:
5949:
5904:
5899:
5828:
5757:
5752:
5742:
5696:
5691:
5681:
5666:
5661:
5631:
5601:
5571:
5551:
5470:
5440:
5280:
5275:
5270:
5265:
5260:
5240:
5210:
5200:
5160:
5155:
5150:
5145:
5130:
5115:
5070:
5065:
5060:
5055:
5020:
5010:
5005:
4990:
4914:
4878:
4839:
4818:
4772:
4726:
4690:
4638:
4587:
4572:
4537:
4446:
4376:
4371:
4356:
4351:
4304:
4281:
4255:
4240:
4194:
4168:
4163:
4158:
4153:
4148:
4143:
3985:
3959:
3914:
3904:
3889:
3816:
3795:
3790:
3785:
3764:
3759:
3754:
3685:
3517:
3435:
3311:
3264:
3259:
2863:
2736:
2731:
2665:
2552:
2497:
2492:
2487:
2483:
2475:
2445:
2348:
2343:
2333:
2328:
2308:
2293:
2266:
2256:
2246:
2236:
2192:
2187:
2182:
2177:
2147:
2142:
2137:
1595:"CDC - Influenza (Flu) | Antivirals: Side-Effects | REMOVED!"
1116:
993:
988:
907:
882:
761:
737:
685:
681:
669:
641:
637:
511:
342:
1510:
862:
Rimantadine shows fewer CNS symptoms than its sister drug amantadine.
732:
mixture; the R and S states are both present in the drug. Solid state
6039:
6019:
5984:
5929:
5924:
5879:
5833:
5823:
5616:
5611:
5556:
5516:
5435:
5425:
5415:
5405:
5320:
5195:
5135:
5125:
5100:
5090:
5080:
5040:
4980:
4975:
4894:
4849:
4792:
4787:
4721:
4716:
4711:
4695:
4653:
4648:
4542:
4527:
4426:
4391:
4291:
4219:
4214:
3924:
3899:
3884:
3857:
3826:
3821:
3744:
3729:
3569:
3564:
3344:
3303:
3296:
3291:
2819:
2690:
2660:
2530:
2525:
2470:
2456:
2313:
2303:
2241:
2119:
2086:
1411:
1254:
998:
903:
785:
297:
240:
64:
2041:
U.S. Center for Drug
Evaluation and Research rimantadine description
1495:
651:
Rimantadine was approved for medical use in 1993. Seasonal H3N2 and
6029:
5864:
5782:
5716:
5395:
5370:
5345:
5335:
5045:
5030:
4960:
4870:
4808:
4803:
4777:
4628:
4612:
4476:
4317:
4209:
4173:
4138:
4058:
4004:
4000:
3990:
3929:
3724:
3664:
2231:
849:
391:
322:
534:
438:
5894:
5732:
5521:
5350:
5120:
4970:
4965:
4934:
4336:
4235:
4230:
3479:
2685:
2323:
2318:
1987:
United States Patent № 4551552: Process for preparing rimantadine
1971:
United States Patent № 4551552: Process for preparing rimantadine
1852:"rimantadine (NMDA OR NMDAR OR NMDARs OR "N-methyl-D-aspartate")"
835:
1750:
Danysz W, Dekundy A, Scheschonka A, Riederer P (February 2021).
1749:
1460:
6034:
5000:
4854:
4731:
4296:
3675:
3349:
2670:
2640:
960:
827:
723:
402:
245:
1997:
1531:
926:
of rimantadine are known to act as NMDA receptor antagonists.
28:
5854:
4955:
3549:
1714:
741:
525:
213:
2788:
1743:
455:
2281:
2212:
2123:
693:
382:
1708:
1033:
Govorkova EA, Fang HB, Tan M, Webster RG (December 2004).
4782:
1924:
1489:
1454:
2036:
U.S. FDA press release announcing rimantadine's approval
1875:
1362:
1169:
Principles and
Practice of Pediatric Infectious Disease
1032:
1303:
1119:"Amantadine and rimantadine for influenza A in adults"
668:
Rimantadine inhibits influenza activity by binding to
1869:
728:
Rimantadine, when sold as flumadine, is present as a
1165:
800:. Rimantadine has also been shown to treat chronic
6136:
4103:
1566:
310:
285:
3641:
1818:
1206:Journal of Biomolecular Structure and Dynamics
885:also affects the body's uptake of rimantadine.
4089:
3627:
2804:
2071:
2051:U.S. CDC flu anti-viral treatment information
1844:
768:activity and can be used in the treatment of
16:Drug used to treat influenzavirus A infection
4835:Deoxyepinephrine (N-methyldopamine, epinine)
4277:Deoxyepinephrine (N-methyldopamine, epinine)
973:, 1965 and on the first method of synthesis
724:Rimantadine enantiomers interactions with M2
1297:
1123:The Cochrane Database of Systematic Reviews
1026:
4096:
4082:
3634:
3620:
2811:
2797:
2078:
2064:
1172:. Elsevier Health Sciences. p. 1502.
631:used to treat, and in rare cases prevent,
469:
350:
1901:
1792:
1775:
1679:
1613:
1437:
1388:
1339:
1329:
1280:
1166:Long SS, Pickering LK, Prober CG (2012).
1142:
1081:
1058:
1022:https://www.rxlist.com/flumadine-drug.htm
370:
1369:Journal of the American Chemical Society
1203:
938:
702:
6160:Drugs with unknown mechanisms of action
5724:Antiemetics/gastroprokinetics/sedatives
760:Rimantadine, like its antiviral cousin
711:
465:
330:
83:
6137:
755:
4077:
4062:
3615:
3601:US influenza statistics by flu season
2792:
2059:
1039:Antimicrobial Agents and Chemotherapy
922:does not seem to have been reported.
431:
410:
164:
69:
4063:
437:
137:
5326:Levomepromazine (methotrimeprazine)
2400:Sofosbuvir/velpatasvir/voxilaprevir
1960:US patent 3352912 to W. W. Prichard
897:
390:
301:
13:
3596:2017–2018 United States flu season
14:
6186:
3335:Live attenuated influenza vaccine
2385:Ombitasvir/paritaprevir/ritonavir
2029:
967:(patent on new chemical compound
707:Rimantadine S31N Mutation Binding
2046:U.S. NIH rimantadine description
1475:10.1097/00002826-199901000-00006
1051:10.1128/AAC.48.12.4855-4863.2004
504:
498:
36:
27:
6107:Monoamine metabolism modulators
1991:
1980:
1964:
1953:
1918:
1798:
1673:
1642:
1607:
1587:
1560:
1525:
1418:ACS Medicinal Chemistry Letters
1405:
1356:
1261:ACS Medicinal Chemistry Letters
892:
865:
807:
658:
594:Key:UBCHPRBFMUDMNC-UHFFFAOYSA-N
2000:Reviews of Infectious Diseases
1927:Journal of Medicinal Chemistry
1534:Reviews of Infectious Diseases
1430:10.1021/acsmedchemlett.6b00311
1273:10.1021/acsmedchemlett.6b00311
1248:
1197:
1186:
1159:
1135:10.1002/14651858.CD001169.pub3
1110:
1075:
1015:
736:studies have shown that the R
663:
492:
1:
6089:Monoamine reuptake inhibitors
6062:Receptor/signaling modulators
4241:Adrogolide (ABT-431, DAS-431)
3393:Russian flu (1889–1890)
2818:
2126:protease inhibitors (–previr)
1729:10.1016/s0149-7634(96)00037-1
1694:10.1016/j.vaccine.2006.11.045
1628:10.1016/j.vaccine.2006.11.045
1218:10.1080/07391102.2020.1747550
1096:10.1016/j.vaccine.2006.11.045
1009:
1655:Food and Drug Administration
934:
929:
906:and to a much lesser extent
875:(acetaminophen, Tylenol) or
646:Food and Drug Administration
627:) is an orally administered
623:, sold under the trade name
7:
982:
10:
6191:
6098:Monoamine releasing agents
5286:Flupentixol (flupenthixol)
4462:Flupentixol (flupenthixol)
3168:Transmission and infection
1768:10.1007/s00702-021-02306-2
954:
700:bound inside the M2 pore.
482:Chemical and physical data
6170:Suspected embryotoxicants
6052:
5950:Metitepine (methiothepin)
5376:Pericyazine (periciazine)
5174:
4800:Dihydrexidine derivatives
4679:
4666:
4639:Metitepine (methiothepin)
4435:
4405:
4227:Dihydrexidine derivatives
4127:
4114:
4071:
4019:
3978:
3870:
3835:
3804:
3773:
3694:
3663:
3654:
3583:
3530:
3505:
3467:
3460:
3448:Central Luzon H5N6 (2017)
3426:
3388:Influenza pandemic (1557)
3383:Influenza pandemic (1510)
3373:
3362:
3325:
3250:
3241:
3221:
3212:
3155:
3119:
3110:
3090:
3062:
3053:
2908:
2872:
2826:
2749:
2714:
2633:
2579:
2551:
2544:
2454:
2430:
2412:
2362:
2280:
2211:
2118:
2109:
1894:10.1016/j.bmc.2008.10.028
1569:Seminars in Liver Disease
912:NMDA receptor antagonists
779:
602:
577:
569:NC(C)C13CC2CC(CC(C1)C2)C3
557:
545:
523:
510:
486:
481:
449:
421:
401:
381:
361:
341:
321:
296:
276:
268:1-(adamantanyl)ethanamine
256:
251:
239:
226:
207:
197:
187:
179:
154:
149:
124:
112:
91:
77:
59:
49:
44:
35:
26:
5552:Clotiapine (clothiapine)
5426:Spiperone (spiroperidol)
5391:Piflutixol (pifluthixol)
3490:2007 Australian outbreak
2512:neuraminidase inhibitors
2375:Glecaprevir/pibrentasvir
1756:J Neural Transm (Vienna)
855:Difficulty concentrating
812:Rimantadine can produce
790:Saint Louis encephalitis
674:M2 transmembrane channel
6165:Proton channel blockers
5508:Atypical antipsychotics
4891:Atypical antipsychotics
4824:N,N-Propyldihydrexidine
4524:Atypical antipsychotics
4413:Tetrahydroisoquinolines
3277:Neuraminidase inhibitor
2012:10.1093/clinids/3.3.408
1546:10.1093/clinids/3.3.408
1331:10.1073/pnas.0804958105
918:of rimantadine for the
692:specified by virion M2
5182:Typical antipsychotics
4443:Typical antipsychotics
3591:Influenza-like illness
3260:Adamantane derivatives
2715:Multiple/Unknown/Other
2484:adamantane derivatives
2395:Sofosbuvir/velpatasvir
2390:Sofosbuvir/daclatasvir
944:
818:central nervous system
708:
6155:Anti-influenza agents
6116:Monoamine neurotoxins
4910:Aripiprazole lauroxil
3441:1989–1990 UK outbreak
3403:Asian flu (1957-1958)
2583:inhibitors (–trelvir)
2571:Peginterferon alfa-2b
2566:Peginterferon alfa-2a
2380:Ledipasvir/sofosbuvir
1717:Neurosci Biobehav Rev
976:U.S. patent 3,592,934
970:U.S. patent 3,352,912
943:Rimantadine synthesis
942:
798:parainfluenza viruses
774:front-line treatments
706:
6175:Suspected teratogens
5885:Desmethoxyfallypride
5096:Propylnorapomorphine
4895:Alentemol (U-66444B)
4367:Propylnorapomorphine
3643:Antiparkinson agents
3408:Hong Kong flu (1968)
3200:Pandemic preparation
2370:Elbasvir/grazoprevir
1381:10.1021/jacs.5b13129
965:Wilmington, Delaware
910:are known to act as
877:acetylsalicylic acid
712:Influenza resistance
6025:Tetrahydropalmatine
4758:Dihydroergocryptine
4397:Tetrahydropalmatine
4200:Dihydroergocryptine
3720:Dihydroergocryptine
2287:inhibitors (–buvir)
2215:inhibitors (–asvir)
1939:10.1021/jm00169a029
1575:(Suppl 1): 95–102.
1463:Clin Neuropharmacol
1322:2008PNAS..10510967J
770:Parkinson's disease
756:Parkinson's disease
682:envelope and capsid
23:
4046:Never to phase III
3398:Spanish flu (1918)
3317:Baloxavir marboxil
3142:West Bengal (2008)
3077:1977 (Russian flu)
3072:1918 (Spanish flu)
2776:Never to phase III
2634:RNA pol inhibitors
2561:Interferon alfa 2b
2466:Baloxavir marboxil
945:
902:The related drugs
848:Trouble sleeping (
709:
19:
6132:
6131:
6126:
6125:
6119:
6110:
6101:
6092:
6083:
6074:
6065:
6048:
6047:
5955:N-Methylspiperone
5813:Trimethobenzamide
4873:
4865:
4857:
4662:
4661:
4320:
4312:
4299:
4105:Dopamine receptor
4056:
4055:
3866:
3865:
3609:
3608:
3526:
3525:
3456:
3455:
3436:Fujian flu (H3N2)
3358:
3357:
3237:
3236:
3208:
3207:
3163:Genetic structure
3106:
3105:
2910:Influenza A virus
2849:Genome sequencing
2786:
2785:
2745:
2744:
2408:
2407:
2363:Combination drugs
1888:(23): 9925–9936.
1511:10.1002/mds.20471
961:Du Pont & Co.
746:electrophysiology
678:viral replication
653:2009 pandemic flu
640:are derivates of
614:
613:
536:Interactive image
451:CompTox Dashboard
168:
105:
6182:
6113:
6104:
6095:
6086:
6077:
6068:
6056:
5935:Levofenfluramine
5803:Thiethylperazine
5480:+tranylcypromine
5411:Prochlorperazine
5226:Chlorproethazine
4871:
4863:
4858:-DOPA (levodopa)
4855:
4677:
4676:
4511:+tranylcypromine
4318:
4310:
4300:-DOPA (levodopa)
4297:
4125:
4124:
4098:
4091:
4084:
4075:
4074:
4065:Pharmacodynamics
4060:
4059:
3895:Chlorphenoxamine
3872:Anticholinergics
3661:
3660:
3636:
3629:
3622:
3613:
3612:
3540:Acute bronchitis
3465:
3464:
3418:Swine flu (2009)
3413:1977 Russian flu
3371:
3370:
3307:
3248:
3247:
3219:
3218:
3117:
3116:
3082:2009 (Swine flu)
3060:
3059:
2880:Orthomyxoviridae
2813:
2806:
2799:
2790:
2789:
2549:
2548:
2545:Multiple/general
2116:
2115:
2080:
2073:
2066:
2057:
2056:
2024:
2023:
1995:
1989:
1984:
1978:
1968:
1962:
1957:
1951:
1950:
1922:
1916:
1915:
1905:
1873:
1867:
1866:
1864:
1862:
1848:
1842:
1841:
1839:
1837:
1822:
1816:
1815:
1813:
1811:
1796:
1790:
1789:
1779:
1747:
1741:
1740:
1712:
1706:
1705:
1677:
1671:
1670:
1668:
1667:
1662:on June 30, 2005
1658:. Archived from
1646:
1640:
1639:
1611:
1605:
1604:
1602:
1601:
1591:
1585:
1584:
1564:
1558:
1557:
1529:
1523:
1522:
1493:
1487:
1486:
1458:
1452:
1451:
1441:
1409:
1403:
1402:
1392:
1360:
1354:
1353:
1343:
1333:
1316:(31): 10967–72.
1301:
1295:
1294:
1284:
1252:
1246:
1245:
1212:(7): 2352–2363.
1201:
1195:
1190:
1184:
1183:
1163:
1157:
1156:
1146:
1114:
1108:
1107:
1079:
1073:
1072:
1062:
1030:
1024:
1019:
978:
972:
898:Pharmacodynamics
814:gastrointestinal
766:antiparkinsonian
633:influenzavirus A
610:
609:
538:
518:
506:
500:
494:
474:
473:
459:
457:
441:
435:
414:
394:
374:
354:
334:
314:
304:
303:
289:
235:25.4 ± 6.3 hours
231:
166:
163:
141:
103:
87:
73:
40:
31:
24:
22:
18:
6190:
6189:
6185:
6184:
6183:
6181:
6180:
6179:
6135:
6134:
6133:
6128:
6127:
6122:
6044:
5820:Antidepressants
5486:Triflupromazine
5476:Trifluoperazine
5456:Thioproperazine
5236:Chlorprothixene
5170:
4831:Phenethylamines
4671:
4658:
4507:Trifluoperazine
4457:Chlorprothixene
4431:
4401:
4268:Phenethylamines
4119:
4110:
4102:
4067:
4057:
4052:
4051:
4036:Clinical trials
4015:
4001:Methylxanthines
3974:
3965:Trihexyphenidyl
3940:Phenglutarimide
3920:Etybenzatropine
3910:Diphenhydramine
3862:
3831:
3800:
3769:
3690:
3650:
3640:
3610:
3605:
3579:
3522:
3501:
3452:
3422:
3367:
3365:
3354:
3321:
3305:
3252:Antiviral drugs
3233:
3204:
3190:Human mortality
3183:clinical trials
3151:
3102:
3086:
3049:
2913:
2911:
2904:
2868:
2822:
2817:
2787:
2782:
2781:
2766:Clinical trials
2741:
2710:
2629:
2575:
2540:
2450:
2426:
2404:
2358:
2276:
2207:
2105:
2084:
2032:
2027:
1996:
1992:
1985:
1981:
1969:
1965:
1958:
1954:
1923:
1919:
1882:Bioorg Med Chem
1874:
1870:
1860:
1858:
1850:
1849:
1845:
1835:
1833:
1826:"PDSP Database"
1824:
1823:
1819:
1809:
1807:
1797:
1793:
1748:
1744:
1713:
1709:
1688:(11): 2019–26.
1678:
1674:
1665:
1663:
1648:
1647:
1643:
1622:(11): 2019–26.
1612:
1608:
1599:
1597:
1593:
1592:
1588:
1565:
1561:
1530:
1526:
1494:
1490:
1459:
1455:
1410:
1406:
1361:
1357:
1302:
1298:
1253:
1249:
1202:
1198:
1191:
1187:
1180:
1164:
1160:
1129:(2): CD001169.
1115:
1111:
1090:(11): 2019–26.
1080:
1076:
1045:(12): 4855–63.
1031:
1027:
1020:
1016:
1012:
985:
974:
968:
957:
937:
932:
900:
895:
868:
844:Lightheadedness
821:adverse effects
810:
782:
758:
742:Antiviral assay
726:
714:
666:
661:
648:(FDA) in 1994.
605:
603:
598:
595:
590:
585:
584:
573:
570:
565:
564:
552:Racemic mixture
541:
516:
503:
497:
477:
453:
445:
417:
397:
377:
357:
337:
317:
300:
292:
272:
269:
264:
263:
229:
221:glucuronidation
199:Protein binding
189:Bioavailability
181:Pharmacokinetic
175:
145:
115:
108:
104:(United States)
94:
17:
12:
11:
5:
6188:
6178:
6177:
6172:
6167:
6162:
6157:
6152:
6147:
6130:
6129:
6124:
6123:
6121:
6120:
6111:
6102:
6093:
6084:
6075:
6066:
6053:
6050:
6049:
6046:
6045:
6043:
6042:
6037:
6032:
6027:
6022:
6017:
6012:
6007:
6002:
5997:
5992:
5987:
5982:
5977:
5972:
5967:
5962:
5957:
5952:
5947:
5942:
5937:
5932:
5927:
5922:
5920:Isocorypalmine
5917:
5912:
5907:
5902:
5897:
5892:
5887:
5882:
5877:
5872:
5867:
5862:
5857:
5847:
5846:
5841:
5836:
5831:
5826:
5816:
5815:
5810:
5805:
5800:
5795:
5790:
5788:Metoclopramide
5785:
5780:
5775:
5770:
5765:
5763:Deudomperidone
5760:
5755:
5750:
5745:
5740:
5735:
5730:
5728:Aceprometazine
5720:
5719:
5714:
5709:
5704:
5699:
5694:
5689:
5684:
5679:
5674:
5669:
5664:
5659:
5654:
5652:Piperacetazine
5649:
5644:
5639:
5629:
5624:
5619:
5614:
5609:
5604:
5599:
5594:
5589:
5584:
5579:
5574:
5569:
5564:
5559:
5554:
5549:
5544:
5539:
5534:
5529:
5524:
5519:
5514:
5504:
5503:
5501:Zuclopenthixol
5498:
5493:
5488:
5483:
5473:
5468:
5463:
5458:
5453:
5448:
5443:
5438:
5433:
5428:
5423:
5418:
5413:
5408:
5403:
5398:
5393:
5388:
5385:+amitriptyline
5378:
5373:
5368:
5363:
5358:
5353:
5348:
5343:
5338:
5333:
5328:
5323:
5318:
5313:
5308:
5303:
5298:
5293:
5283:
5278:
5273:
5268:
5263:
5258:
5253:
5248:
5243:
5238:
5233:
5231:Chlorpromazine
5228:
5223:
5218:
5213:
5208:
5203:
5198:
5193:
5191:Acetophenazine
5188:
5178:
5176:
5172:
5171:
5169:
5168:
5163:
5158:
5153:
5148:
5143:
5138:
5133:
5128:
5123:
5118:
5113:
5108:
5103:
5098:
5093:
5088:
5083:
5078:
5073:
5068:
5063:
5058:
5053:
5048:
5043:
5038:
5033:
5028:
5023:
5018:
5013:
5008:
5003:
4998:
4993:
4988:
4983:
4978:
4973:
4968:
4963:
4958:
4948:
4947:
4942:
4937:
4932:
4927:
4922:
4917:
4912:
4907:
4897:
4887:
4886:
4881:
4876:
4868:
4866:-Phenylalanine
4860:
4852:
4847:
4842:
4837:
4827:
4826:
4821:
4816:
4811:
4806:
4796:
4795:
4790:
4785:
4780:
4775:
4770:
4765:
4760:
4755:
4750:
4745:
4735:
4734:
4729:
4724:
4719:
4714:
4708:Aminotetralins
4704:
4703:
4698:
4693:
4683:
4681:
4674:
4669:
4664:
4663:
4660:
4659:
4657:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4616:
4615:
4610:
4605:
4600:
4595:
4590:
4585:
4580:
4570:
4565:
4560:
4555:
4550:
4545:
4540:
4535:
4530:
4520:
4519:
4517:Zuclopenthixol
4514:
4504:
4499:
4494:
4489:
4486:+amitriptyline
4479:
4474:
4469:
4459:
4454:
4452:Chlorpromazine
4449:
4439:
4437:
4433:
4432:
4430:
4429:
4424:
4419:
4409:
4407:
4403:
4402:
4400:
4399:
4394:
4389:
4384:
4379:
4374:
4369:
4364:
4359:
4354:
4349:
4347:Isocorypalmine
4344:
4339:
4329:
4328:
4323:
4315:
4313:-Phenylalanine
4307:
4302:
4294:
4289:
4284:
4279:
4274:
4264:
4263:
4258:
4253:
4248:
4243:
4238:
4233:
4223:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4182:
4181:
4176:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4131:
4129:
4122:
4117:
4112:
4111:
4101:
4100:
4093:
4086:
4078:
4072:
4069:
4068:
4054:
4053:
4050:
4049:
4048:
4047:
4044:
4033:
4027:
4021:
4020:
4017:
4016:
4014:
4013:
4008:
3998:
3996:Istradefylline
3993:
3988:
3982:
3980:
3976:
3975:
3973:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3932:
3927:
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3882:
3876:
3874:
3868:
3867:
3864:
3863:
3861:
3860:
3855:
3844:
3842:
3833:
3832:
3830:
3829:
3824:
3819:
3813:
3811:
3802:
3801:
3799:
3798:
3793:
3788:
3782:
3780:
3771:
3770:
3768:
3767:
3762:
3757:
3752:
3747:
3742:
3733:
3732:
3727:
3722:
3717:
3712:
3703:
3701:
3692:
3691:
3689:
3688:
3683:
3672:
3670:
3658:
3652:
3651:
3639:
3638:
3631:
3624:
3616:
3607:
3606:
3604:
3603:
3598:
3593:
3587:
3585:
3584:Related topics
3581:
3580:
3578:
3577:
3572:
3567:
3562:
3557:
3552:
3547:
3542:
3536:
3534:
3528:
3527:
3524:
3523:
3521:
3520:
3515:
3509:
3507:
3503:
3502:
3500:
3499:
3494:
3493:
3492:
3482:
3477:
3471:
3469:
3462:
3458:
3457:
3454:
3453:
3451:
3450:
3445:
3444:
3443:
3432:
3430:
3424:
3423:
3421:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3379:
3377:
3368:
3363:
3360:
3359:
3356:
3355:
3353:
3352:
3347:
3342:
3337:
3331:
3329:
3323:
3322:
3320:
3319:
3314:
3309:
3306:(experimental)
3301:
3300:
3299:
3294:
3289:
3284:
3274:
3273:
3272:
3267:
3256:
3254:
3245:
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3147:2020s outbreak
3144:
3139:
3134:
3129:
3127:Croatia (2005)
3123:
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3114:
3108:
3107:
3104:
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3101:
3100:
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2859:Superinfection
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2827:General topics
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2706:Valopicitabine
2703:
2698:
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2285:RNA polymerase
2278:
2277:
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2030:External links
2028:
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1979:
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1952:
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1868:
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1762:(2): 127–169.
1742:
1723:(4): 455–468.
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6080:Serotonergics
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6000:Sonepiprazole
5998:
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5941:
5938:
5936:
5933:
5931:
5928:
5926:
5923:
5921:
5918:
5916:
5915:Iodobenzamide
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5881:
5878:
5876:
5875:Bromocriptine
5873:
5871:
5868:
5866:
5863:
5861:
5858:
5856:
5852:
5849:
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5845:
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5774:
5771:
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5759:
5756:
5754:
5751:
5749:
5748:Benzquinamide
5746:
5744:
5741:
5739:
5736:
5734:
5731:
5729:
5725:
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5718:
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5598:
5595:
5593:
5590:
5588:
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5568:
5567:DHA-clozapine
5565:
5563:
5560:
5558:
5555:
5553:
5550:
5548:
5545:
5543:
5540:
5538:
5535:
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5520:
5518:
5515:
5513:
5509:
5506:
5505:
5502:
5499:
5497:
5494:
5492:
5491:Trifluperidol
5489:
5487:
5484:
5481:
5477:
5474:
5472:
5469:
5467:
5464:
5462:
5459:
5457:
5454:
5452:
5451:Thiopropazate
5449:
5447:
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5442:
5439:
5437:
5434:
5432:
5431:Sulforidazine
5429:
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5424:
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5409:
5407:
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5357:
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5334:
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5331:Levosulpiride
5329:
5327:
5324:
5322:
5319:
5317:
5314:
5312:
5309:
5307:
5304:
5302:
5301:Fluprothixene
5299:
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5287:
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5282:
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5269:
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5102:
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5076:Phencyclidine
5074:
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4925:Brilaroxazine
4923:
4921:
4920:Brexpiprazole
4918:
4916:
4913:
4911:
4908:
4905:
4901:
4898:
4896:
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4888:
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4841:
4838:
4836:
4832:
4829:
4828:
4825:
4822:
4820:
4817:
4815:
4814:Dihydrexidine
4812:
4810:
4807:
4805:
4801:
4798:
4797:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4764:
4761:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4743:Bromocriptine
4740:
4737:
4736:
4733:
4730:
4728:
4725:
4723:
4720:
4718:
4715:
4713:
4709:
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4609:
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4596:
4594:
4591:
4589:
4586:
4584:
4581:
4578:
4574:
4571:
4569:
4568:Norquetiapine
4566:
4564:
4561:
4559:
4556:
4554:
4551:
4549:
4548:DHA-clozapine
4546:
4544:
4541:
4539:
4536:
4534:
4531:
4529:
4525:
4522:
4521:
4518:
4515:
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4500:
4498:
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4398:
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4380:
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4288:
4285:
4283:
4280:
4278:
4275:
4273:
4269:
4266:
4265:
4262:
4259:
4257:
4254:
4252:
4249:
4247:
4246:Dihydrexidine
4244:
4242:
4239:
4237:
4234:
4232:
4228:
4225:
4224:
4221:
4218:
4216:
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4211:
4208:
4206:
4203:
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4109:
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4022:
4018:
4012:
4009:
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3999:
3997:
3994:
3992:
3989:
3987:
3984:
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3981:
3977:
3971:
3968:
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3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3737:Non-ergoline:
3735:
3734:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3710:Bromocriptine
3708:
3705:
3704:
3702:
3700:
3697:
3693:
3687:
3684:
3681:
3677:
3674:
3673:
3671:
3669:
3666:
3662:
3659:
3657:
3656:Dopaminergics
3653:
3648:
3644:
3637:
3632:
3630:
3625:
3623:
3618:
3617:
3614:
3602:
3599:
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3588:
3586:
3582:
3576:
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3545:Bronchiolitis
3543:
3541:
3538:
3537:
3535:
3533:
3532:Complications
3529:
3519:
3518:Fujian (H5N1)
3516:
3514:
3511:
3510:
3508:
3504:
3498:
3495:
3491:
3488:
3487:
3486:
3483:
3481:
3478:
3476:
3473:
3472:
3470:
3466:
3463:
3459:
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3419:
3416:
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3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3380:
3378:
3376:
3372:
3369:
3364:Pandemics and
3361:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
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3330:
3328:
3324:
3318:
3315:
3313:
3310:
3308:
3302:
3298:
3295:
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3290:
3288:
3285:
3283:
3280:
3279:
3278:
3275:
3271:
3268:
3266:
3263:
3262:
3261:
3258:
3257:
3255:
3253:
3249:
3246:
3244:
3240:
3230:
3227:
3226:
3224:
3220:
3217:
3215:
3211:
3201:
3198:
3196:
3195:Social impact
3193:
3191:
3188:
3184:
3181:
3180:
3179:
3176:
3174:
3173:Global spread
3171:
3169:
3166:
3164:
3161:
3160:
3158:
3154:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3124:
3122:
3118:
3115:
3113:
3109:
3099:
3096:
3095:
3093:
3089:
3083:
3080:
3078:
3075:
3073:
3070:
3069:
3067:
3065:
3061:
3058:
3056:
3052:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2917:
2915:
2907:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2877:
2875:
2871:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2831:
2829:
2825:
2821:
2814:
2809:
2807:
2802:
2800:
2795:
2794:
2791:
2775:
2773:
2770:
2769:
2767:
2764:
2761:
2758:
2756:
2753:
2752:
2748:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2719:
2717:
2713:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2638:
2636:
2632:
2625:
2621:
2618:
2616:
2613:
2610:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2587:
2585:
2582:
2578:
2572:
2569:
2567:
2564:
2562:
2559:
2558:
2556:
2554:
2550:
2547:
2543:
2536:
2532:
2529:
2527:
2524:
2522:
2518:
2517:
2516:release phase
2513:
2509:
2508:
2504:
2501:
2499:
2496:
2494:
2490:
2489:
2488:M2 inhibitors
2485:
2481:
2480:
2477:
2474:
2472:
2469:
2467:
2464:
2463:
2461:
2458:
2453:
2447:
2444:
2442:
2438:
2437:
2435:
2433:
2429:
2423:
2420:
2419:
2417:
2415:
2411:
2401:
2398:
2396:
2393:
2391:
2388:
2386:
2383:
2381:
2378:
2376:
2373:
2371:
2368:
2367:
2365:
2361:
2355:
2352:
2350:
2347:
2345:
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2305:
2302:
2300:
2299:Bemnifosbuvir
2297:
2295:
2292:
2291:
2289:
2286:
2283:
2279:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2219:
2217:
2214:
2210:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2130:
2128:
2125:
2121:
2117:
2114:
2112:
2108:
2103:
2099:
2095:
2091:
2088:
2081:
2076:
2074:
2069:
2067:
2062:
2061:
2058:
2052:
2049:
2047:
2044:
2042:
2039:
2037:
2034:
2033:
2021:
2017:
2013:
2009:
2006:(3): 408–21.
2005:
2001:
1994:
1988:
1983:
1977:
1972:
1967:
1961:
1956:
1948:
1944:
1940:
1936:
1933:(7): 1992–5.
1932:
1928:
1921:
1913:
1909:
1904:
1899:
1895:
1891:
1887:
1883:
1879:
1872:
1857:
1853:
1847:
1831:
1827:
1821:
1806:
1802:
1799:Liu, Tiqing.
1795:
1787:
1783:
1778:
1773:
1769:
1765:
1761:
1757:
1753:
1746:
1738:
1734:
1730:
1726:
1722:
1718:
1711:
1703:
1699:
1695:
1691:
1687:
1683:
1676:
1661:
1657:
1656:
1651:
1645:
1637:
1633:
1629:
1625:
1621:
1617:
1610:
1596:
1590:
1582:
1578:
1574:
1570:
1563:
1555:
1551:
1547:
1543:
1540:(3): 408–21.
1539:
1535:
1528:
1520:
1516:
1512:
1508:
1504:
1500:
1492:
1484:
1480:
1476:
1472:
1468:
1464:
1457:
1449:
1445:
1440:
1435:
1431:
1427:
1423:
1419:
1415:
1408:
1400:
1396:
1391:
1386:
1382:
1378:
1375:(5): 1506–9.
1374:
1370:
1366:
1359:
1351:
1347:
1342:
1337:
1332:
1327:
1323:
1319:
1315:
1311:
1307:
1300:
1292:
1288:
1283:
1278:
1274:
1270:
1266:
1262:
1258:
1251:
1243:
1239:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1207:
1200:
1194:
1189:
1181:
1175:
1171:
1170:
1162:
1154:
1150:
1145:
1140:
1136:
1132:
1128:
1124:
1120:
1113:
1105:
1101:
1097:
1093:
1089:
1085:
1078:
1070:
1066:
1061:
1056:
1052:
1048:
1044:
1040:
1036:
1029:
1023:
1018:
1014:
1005:
1002:
1000:
997:
995:
992:
990:
987:
986:
980:
977:
971:
966:
962:
952:
949:
941:
927:
925:
921:
920:NMDA receptor
917:
913:
909:
905:
887:
884:
881:
878:
874:
870:
869:
863:
857:
854:
851:
847:
845:
842:
839:
837:
834:
832:Upset stomach
831:
829:
826:
825:
824:
822:
819:
815:
805:
803:
799:
795:
791:
787:
777:
775:
771:
767:
763:
753:
750:
747:
743:
739:
735:
731:
721:
717:
705:
701:
697:
695:
691:
687:
683:
679:
675:
671:
656:
654:
649:
647:
643:
639:
634:
630:
626:
622:
618:
608:
601:
592:
587:
586:
583:
576:
567:
566:
563:
556:
553:
550:
548:
544:
537:
533:
532:
530:
527:
522:
515:
513:
509:
491:
489:
485:
480:
472:
468:
467:DTXSID2023561
464:
463:
461:
452:
448:
440:
439:RCSB PDB
434:
429:
428:
426:
424:
420:
413:
409:
408:
406:
404:
400:
393:
389:
388:
386:
384:
380:
373:
369:
368:
366:
364:
360:
353:
349:
348:
346:
344:
340:
333:
329:
328:
326:
324:
320:
313:
309:
308:
306:
299:
295:
288:
284:
283:
281:
279:
275:
266:
265:
262:
255:
250:
247:
244:
242:
238:
234:
232:
225:
222:
218:
217:hydroxylation
215:
212:
210:
206:
202:
200:
196:
193:well absorbed
192:
190:
186:
182:
178:
172:
162:
161:
159:
157:
153:
148:
140:
135:
132:
131:
129:
127:
123:
119:
117:
111:
101:
100:
98:
96:
90:
86:
82:
80:
76:
72:
68:
66:
62:
58:
54:
52:
48:
45:Clinical data
43:
39:
34:
30:
25:
6114:
6105:
6096:
6087:
6078:
6069:
6058:
6057:
6010:Stepholidine
6005:Spiroxatrine
5995:Seridopidine
5990:SB-277,011-A
5910:Fenfluramine
5870:Bromerguride
5850:
5844:Trimipramine
5839:Propiomazine
5819:
5798:Promethazine
5793:Metopimazine
5723:
5642:Paliperidone
5587:Fluperlapine
5577:Elopiprazole
5542:Clocapramine
5532:Carpipramine
5507:
5461:Thioridazine
5421:Prothipendyl
5381:Perphenazine
5341:Mesoridazine
5316:Homopipramol
5306:Fluspirilene
5296:Fluphenazine
5251:Clothixamide
5246:Clopenthixol
5221:Chloracizine
5216:Butaperazine
5186:Acepromazine
5181:
5141:Salvinorin A
4951:
4945:Norclozapine
4940:Lumateperone
4900:Aripiprazole
4890:
4830:
4799:
4753:Chanoclavine
4738:
4707:
4700:
4686:
4619:
4583:Paliperidone
4563:Norclozapine
4553:Fluperlapine
4523:
4497:Thioridazine
4482:Perphenazine
4472:Fluphenazine
4442:
4412:
4387:Stepholidine
4332:
4267:
4226:
4185:
4135:Benzazepines
4134:
4010:
3950:Procyclidine
3935:Orphenadrine
3880:Benzatropine
3736:
3706:
3680:+benserazide
3575:Strep throat
3555:Otitis media
3269:
3132:India (2006)
2854:Reassortment
2681:Molnupiravir
2676:Mericitabine
2646:Deuremidevir
2620:Simnotrelvir
2605:Nirmatrelvir
2595:Ibuzatrelvir
2581:3CL protease
2510:
2502:
2482:
2439:
2432:Picornavirus
2354:Uprifosbuvir
2252:Pibrentasvir
2203:Voxilaprevir
2173:Paritaprevir
2003:
1999:
1993:
1982:
1974:
1966:
1955:
1930:
1926:
1920:
1885:
1881:
1871:
1861:13 September
1859:. Retrieved
1855:
1846:
1836:13 September
1834:. Retrieved
1829:
1820:
1810:13 September
1808:. Retrieved
1804:
1794:
1759:
1755:
1745:
1720:
1716:
1710:
1685:
1681:
1675:
1664:. Retrieved
1660:the original
1653:
1644:
1619:
1615:
1609:
1598:. Retrieved
1589:
1572:
1568:
1562:
1537:
1533:
1527:
1502:
1498:
1491:
1469:(1): 30–32.
1466:
1462:
1456:
1421:
1417:
1407:
1372:
1368:
1358:
1313:
1309:
1299:
1264:
1260:
1250:
1209:
1205:
1199:
1188:
1168:
1161:
1126:
1122:
1112:
1087:
1083:
1077:
1042:
1038:
1028:
1017:
1004:Tromantadine
958:
950:
946:
901:
893:Pharmacology
866:Interactions
861:
811:
808:Side effects
783:
764:, possesses
759:
751:
727:
718:
715:
698:
667:
659:Medical uses
650:
624:
616:
615:
604:
228:Elimination
156:Legal status
150:Legal status
6145:Adamantanes
6071:Adrenergics
5975:Pridopidine
5960:Nafadotride
5945:Metergoline
5860:Alpiropride
5808:Trazpiroben
5778:Hydroxyzine
5773:Eticlopride
5768:Domperidone
5738:Alimemazine
5712:Ziprasidone
5707:Zicronapine
5702:Veralipride
5687:Tefludazine
5677:Risperidone
5672:Remoxipride
5657:Pipotiazine
5647:Perospirone
5636:+fluoxetine
5627:Ocaperidone
5622:Mosapramine
5607:Mazapertine
5597:Iloperidone
5592:Gevotroline
5582:Flumezapine
5562:Cyamemazine
5547:Clorotepine
5527:Blonanserin
5512:Amisulpride
5466:Thiothixene
5401:Pipamperone
5366:Perathiepin
5361:Penfluridol
5356:Nemonapride
5311:Haloperidol
5290:+melitracen
5256:Clopimozide
5206:Bromperidol
5175:Antagonists
5166:WAY-100,635
5111:Quinelorane
5106:Quinagolide
5086:Pramipexole
5051:Pardoprunox
5036:Mesulergine
5026:Flibanserin
5016:Dizocilpine
4996:Armodafinil
4986:Apomorphine
4930:Cariprazine
4904:+sertraline
4845:Etilevodopa
4768:Ergocornine
4763:Epicriptine
4748:Cabergoline
4701:Rimantadine
4687:Adamantanes
4608:Ziprasidone
4603:Zicronapine
4598:Tefludazine
4593:Risperidone
4577:+fluoxetine
4558:Iloperidone
4533:Clorotepine
4502:Thiothixene
4492:Pifluthixol
4466:+melitracen
4436:Antagonists
4342:Apomorphine
4287:Etilevodopa
4261:Doxanthrine
4251:Dinapsoline
4190:Cabergoline
4032:from market
4011:Rimantadine
3970:Tropatepine
3955:Profenamine
3945:Piroheptine
3848:Benserazide
3750:Pramipexole
3740:Apomorphine
3715:Cabergoline
3696:DA receptor
3560:Pharyngitis
3506:Non-mammals
3287:Laninamivir
3282:Oseltamivir
3270:Rimantadine
3098:2009 A/H1N1
2900:Influenza D
2895:Influenza C
2890:Influenza B
2885:Influenza A
2762:from market
2727:Merimepodib
2701:Triazavirin
2696:Taribavirin
2656:Galidesivir
2651:Favipiravir
2615:Rupintrivir
2600:Lufotrelvir
2590:Ensitrelvir
2535:Laninamivir
2521:Oseltamivir
2503:Rimantadine
2441:viral entry
2422:Bulevirtide
2414:Hepatitis D
2272:Velpatasvir
2227:Daclatasvir
2222:Coblopasvir
2198:Vedroprevir
2168:Narlaprevir
2163:Grazoprevir
2158:Glecaprevir
2153:Faldaprevir
2133:Asunaprevir
2111:Hepatitis C
2092:(primarily
873:paracetamol
836:Nervousness
802:hepatitis C
786:arboviruses
690:ion channel
670:amino acids
664:Influenza A
617:Rimantadine
519: g·mol
252:Identifiers
79:MedlinePlus
51:Trade names
21:Rimantadine
6139:Categories
5980:Raclopride
5970:PNU-99,194
5965:Nuciferine
5905:Fananserin
5900:Fallypride
5829:Nefazodone
5758:Clebopride
5753:Bromopride
5743:Alizapride
5697:Tiospirone
5692:Tenilapine
5682:Sertindole
5667:Quetiapine
5662:Piquindone
5632:Olanzapine
5602:Lurasidone
5572:Dixyrazine
5537:Cinuperone
5496:Zetidoline
5471:Timiperone
5446:Teflutixol
5441:Sultopride
5281:Fluotracen
5276:Flucindole
5271:Fluanisone
5266:Fluacizine
5261:Droperidol
5241:Ciclindole
5211:Butaclamol
5201:Benperidol
5161:Umespirone
5156:Talipexole
5151:Sumanirole
5146:SKF-83,959
5131:Ropinirole
5116:Quinpirole
5071:PF-592,379
5066:PF-219,061
5061:PD-168,077
5056:PD-128,907
5021:Esketamine
5011:CP-226,269
5006:Captodiame
4991:Arketamine
4915:Bifeprunox
4879:Melevodopa
4840:Dopexamine
4819:Dinoxyline
4773:Lergotrile
4727:Rotigotine
4691:Amantadine
4588:Quetiapine
4573:Olanzapine
4538:Clotiapine
4447:Butaclamol
4382:SKF-89,626
4377:SKF-89,145
4372:Rotigotine
4362:PF 6669571
4357:PF-6649751
4352:Nuciferine
4305:Melevodopa
4282:Dopexamine
4256:Dinoxyline
4195:CY-208,243
4179:Zelandopam
4169:SKF-83,959
4164:SKF-82,958
4159:SKF-81,297
4154:SKF-77,434
4149:SKF-38,393
4144:Fenoldopam
4108:modulators
3986:Amantadine
3960:Tigloidine
3915:Etanautine
3905:Dexetimide
3890:Bornaprine
3840:inhibitors
3817:Entacapone
3809:inhibitors
3796:Selegiline
3791:Safinamide
3786:Rasagiline
3778:inhibitors
3765:Talipexole
3760:Rotigotine
3755:Ropinirole
3686:Melevodopa
3668:precursors
3312:Umifenovir
3304:Peramivir
3265:Amantadine
3243:Treatments
2864:Flu season
2737:Presatovir
2732:Moroxydine
2666:Remdesivir
2624:+ritonavir
2609:+ritonavir
2553:Interferon
2498:Amantadine
2493:Adapromine
2476:Umifenovir
2446:Pleconaril
2349:Radalbuvir
2344:TMC-647055
2334:Sofosbuvir
2329:Setrobuvir
2309:Deleobuvir
2294:Beclabuvir
2267:Samatasvir
2257:Ravidasvir
2247:Ombitasvir
2237:Ledipasvir
2193:Vaniprevir
2188:Telaprevir
2183:Sovaprevir
2178:Simeprevir
2148:Danoprevir
2143:Ciluprevir
2138:Boceprevir
2090:antivirals
1666:2008-11-05
1600:2008-11-05
1499:Mov Disord
1010:References
994:Bromantane
989:Adapromine
908:amantadine
883:Cimetidine
762:amantadine
738:enantiomer
686:M2 protein
642:adamantane
638:amantadine
524:3D model (
512:Molar mass
423:PDB ligand
372:0T2EF4JQTU
343:ChemSpider
287:13392-28-4
278:CAS Number
261:IUPAC name
209:Metabolism
6059:See also:
6040:Yohimbine
6020:Terguride
5985:Sarizotan
5930:L-745,870
5925:L-741,626
5880:Buspirone
5834:Opipramol
5824:Amoxapine
5617:Molindone
5612:Melperone
5557:Clozapine
5517:Asenapine
5436:Sulpiride
5416:Promazine
5406:Preclamol
5321:Lenperone
5196:Azaperone
5136:Roxindole
5126:Ro10-5824
5101:Pukateine
5091:Preclamol
5081:Piribedil
5041:Modafinil
4981:Aplindore
4976:Adrafinil
4874:-Tyrosine
4850:Ibopamine
4793:Terguride
4788:Pergolide
4739:Ergolines
4722:8-OH-PBZI
4717:7-OH-DPAT
4712:5-OH-DPAT
4696:Memantine
4654:SCH-23390
4649:Perlapine
4624:Berupipam
4543:Clozapine
4528:Asenapine
4427:Mevidalen
4392:Tavapadon
4321:-Tyrosine
4292:Ibopamine
4220:Terguride
4215:Pergolide
4186:Ergolines
4042:Phase III
4030:Withdrawn
3925:Mazaticol
3900:Cycrimine
3885:Biperiden
3858:Carbidopa
3852:+levodopa
3827:Tolcapone
3822:Opicapone
3745:Piribedil
3730:Pergolide
3707:Ergoline:
3570:Sinusitis
3565:Pneumonia
3461:Non-human
3428:Epidemics
3375:Pandemics
3366:epidemics
3345:Pandemrix
3297:Zanamivir
3292:Peramivir
3229:2020–2022
3222:Outbreaks
3137:UK (2007)
3120:Outbreaks
3064:Pandemics
2844:Treatment
2820:Influenza
2772:Phase III
2760:Withdrawn
2691:Ribavirin
2661:GS-441524
2531:Peramivir
2526:Zanamivir
2471:Pimodivir
2457:influenza
2339:Tegobuvir
2314:Filibuvir
2304:Dasabuvir
2242:Odalasvir
2087:RNA virus
1832:(in Zulu)
1805:BindingDB
1650:"fda.gov"
1242:214681984
1226:0739-1102
999:Memantine
935:Synthesis
930:Chemistry
924:Analogues
904:memantine
858:Confusion
840:Tiredness
625:Flumadine
547:Chirality
412:ChEMBL959
241:Excretion
230:half-life
114:Routes of
93:Pregnancy
71:Monograph
65:Drugs.com
55:Flumadine
6030:Tiapride
5940:LEK-8829
5865:Azapride
5783:Itopride
5717:Zotepine
5396:Pimozide
5371:Perazine
5346:Moperone
5336:Loxapine
5046:OSU-6162
5031:Ketamine
4961:A-412997
4809:Ciladopa
4804:2-OH-NPA
4778:Lisuride
4680:Agonists
4644:Odapipam
4629:Ecopipam
4613:Zotepine
4477:Loxapine
4210:Lisuride
4205:LEK-8829
4174:Trepipam
4139:6-Br-APB
4128:Agonists
4005:caffeine
3991:Budipine
3930:Metixene
3725:Lisuride
3699:agonists
3676:Levodopa
3327:Vaccines
2912:subtypes
2834:Research
2262:Ruzasvir
2232:Elbasvir
1976:hydride.
1912:18954995
1786:33624170
1702:17258359
1636:17258359
1581:10349697
1519:15809995
1483:10047931
1448:28217261
1399:26804976
1350:18669647
1291:28217261
1234:32212957
1153:16625539
1104:17258359
1069:15561867
983:See also
916:affinity
850:insomnia
607:(verify)
323:DrugBank
126:ATC code
95:category
5895:F-15063
5733:AS-8112
5522:BL-1020
5351:Naranol
5121:RDS-127
4971:ABT-724
4966:ABT-670
4935:F-15063
4884:XP21279
4337:A-68930
4326:XP21279
4272:BCO-001
4236:A-86929
4231:A-77636
4003:(e.g.,
3468:Mammals
3178:Vaccine
3156:Science
3091:Science
2873:Viruses
2839:Vaccine
2686:NITD008
2324:IDX-184
2319:GS-6620
2096:, also
2020:7025146
1947:2362279
1903:7125889
1777:7901515
1737:9195603
1682:Vaccine
1616:Vaccine
1554:7025146
1439:5312807
1390:9328162
1341:2492755
1318:Bibcode
1282:5312807
1144:7068158
1084:Vaccine
955:History
871:Taking
794:Sindbis
730:racemic
672:in the
517:179.307
488:Formula
332:DB00478
298:PubChem
214:Hepatic
142:)
136: (
134:J05AC02
85:a698029
6150:Amines
6035:UH-232
6015:SV-293
5851:Others
5001:BP-897
4952:Others
4732:UH-232
4620:Others
4333:Others
4025:WHO-EM
3979:Others
3485:Equine
3480:Feline
3475:Canine
3350:Audenz
3340:Brands
2755:WHO-EM
2671:MK-608
2641:CMX521
2459:agents
2018:
1945:
1910:
1900:
1856:PubMed
1784:
1774:
1735:
1700:
1634:
1579:
1552:
1517:
1481:
1446:
1436:
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1102:
1067:
1060:529183
1057:
914:. The
828:Nausea
780:Others
562:SMILES
403:ChEMBL
392:D08483
171:℞-only
169:
5855:3-PPP
4956:3-PPP
4672:-like
4120:-like
3775:MAO-B
3550:Croup
3513:Avian
3497:Swine
3045:H11N9
3040:H11N2
3035:H10N8
3030:H10N7
3025:H10N3
2722:EICAR
2455:Anti-
2102:D06BB
2098:S01AD
1238:S2CID
788:like
688:, an
582:InChI
526:JSmol
430:RIM (
246:Renal
5890:EEDQ
4634:EEDQ
4422:DPTQ
4417:DETQ
4406:PAMs
3837:AAAD
3806:COMT
3214:H5N8
3112:H5N1
3055:H1N1
3020:H9N2
3015:H7N9
3010:H7N7
3005:H7N4
3000:H7N3
2995:H7N2
2990:H7N1
2985:H6N1
2980:H5N9
2975:H5N8
2970:H5N6
2965:H5N3
2960:H5N2
2955:H5N1
2950:H3N8
2945:H3N2
2940:H3N1
2935:H2N3
2930:H2N2
2925:H1N2
2920:H1N1
2282:NS5B
2213:NS5A
2100:and
2016:PMID
1943:PMID
1908:PMID
1863:2024
1838:2024
1812:2024
1782:PMID
1733:PMID
1698:PMID
1632:PMID
1577:PMID
1550:PMID
1515:PMID
1479:PMID
1444:PMID
1395:PMID
1346:PMID
1287:PMID
1230:PMID
1222:ISSN
1174:ISBN
1149:PMID
1127:2006
1100:PMID
1065:PMID
816:and
792:and
744:and
694:gene
433:PDBe
383:KEGG
363:UNII
352:4893
312:5071
219:and
183:data
120:Oral
61:AHFS
4783:LSD
3647:N04
2120:NS3
2094:J05
2008:doi
1935:doi
1898:PMC
1890:doi
1830:UNC
1772:PMC
1764:doi
1760:128
1725:doi
1690:doi
1624:doi
1542:doi
1507:doi
1471:doi
1434:PMC
1426:doi
1385:PMC
1377:doi
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1336:PMC
1326:doi
1314:105
1277:PMC
1269:doi
1214:doi
1139:PMC
1131:doi
1092:doi
1055:PMC
1047:doi
734:NMR
621:INN
456:EPA
302:CID
203:40%
139:WHO
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