727:
aqueous solution of a β-lactam antibiotic can denote β-lactamase hydrolysis of amide bonds in the β-lactam ring. This is often observed with a chromogenic β-lactamase substrate like ceftriaxone, merapenem, or nitrocefin, that undergoes a distinctive color change from yellow to red as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase. This color change is a visual indicator of the presence and activity of β-lactamase enzymes, which are responsible for conferring resistance to β-lactam antibiotics in many bacterial species. The hydrolysis of the β-lactam ring by β-lactamase enzymes renders the antibiotic ineffective, thereby allowing the bacteria to survive in the presence of the antibiotic. Some β-lactam antibiotics like ceftriaxone and meropenem are known to be relatively unstable in solution, especially when stored for extended periods, and degrade in an aqueous solution even without the presence of β-lactamase. For ceftriaxone, the color of solutions can range from light yellow to amber, depending on the length of storage, concentration, and diluent used. A study found that meropenem concentrations dropped to 90% of the initial concentration at 7.4 hours at 22°C and 5.7 hours at 33°C, indicating degradation over time.
763:
997:
408:
51:
386:
399:
666:
676:
937:
until the β-carbon of β-lactam is reached, at which point numbering continues counterclockwise around the lactam ring to number the remaining to carbons. For example, the nitrogen atom of all bicyclic β-lactams fused to five-membered rings is labelled position 4, as it is in penams, while in cephems, the nitrogen is position 5.
718:
harbor some level of β-lactamase expression. In this case, failure to use the most appropriate β-lactam antibiotic therapy at the onset of treatment could result in selection for bacteria with higher levels of β-lactamase expression, thereby making further efforts with other β-lactam antibiotics more difficult.
1000:
This figure outlines the different methods of β-lactam closure among the various classes of β-lactam compounds. Penams and cephems are cyclized oxidatively (first row); clavams and carbapenems are closed by ATP-utilizing amidation (second and third row); and some monobactams may be closed by a third
721:
In the context of medical pharmacology, penicillins, cephalosporins, and carbapenems, while all have the β-lactam ring that serves as the fundamental structure, also have an auxiliary ring that carries a carboxylate group that is positioned on the same side as the carbonyl group within the β-lactam
726:
of the β-lactam ring, thereby eliminating the antimicrobial activity of these antibiotics. This resistance mechanism underscores the importance of the structural integrity of the β-lactam ring for the antibiotic's function. The color change from colorless or light yellow to amber or even red in an
1012:
While the ring closure in penams and cephems is between positions 1 and 4 of the β-lactam and is oxidative, the clavams and carbapenems have their rings closed between positions 1 and 2 of the ring. β-lactam synthetases are responsible for these cyclizations, and the carboxylate of the open-ring
936:
By convention, the bicyclic β-lactams are numbered starting with the position occupied by sulfur in the penams and cephems, regardless of which atom it is in a given class. That is, position 1 is always adjacent to the β-carbon of β-lactam ring. The numbering continues clockwise from position one
705:
so that the amoxicillin is not affected by the β-lactamase enzymes. Another β-lactam/β-lactamase inhibitor combination is piperacillin/tazobactam with a broad spectrum of antibacterial activity that includes gram-positive and -negative aerobic and anaerobic bacteria. The addition of tazobactam to
713:
such as boronic acids are being studied in which they irreversibly bind to the active site of β-lactamases. This is a benefit over clavulanic acid and similar beta-lactam competitors, because they cannot be hydrolysed, and therefore rendered useless. Extensive research is currently being done to
717:
However, in all cases where infection with β-lactamase-producing bacteria is suspected, the choice of a suitable β-lactam antibiotic should be carefully considered prior to treatment. In particular, choosing appropriate β-lactam antibiotic therapy is of utmost importance against organisms which
536:. Inhibition of cross-linkage by β-lactams causes a build-up of peptidoglycan precursors, which triggers the digestion of existing peptidoglycan by autolytic hydrolases without the production of new peptidoglycan. As a result, the bactericidal action of β-lactam antibiotics is further enhanced.
735:
As a response to the use of β-lactams to control bacterial infections, some bacteria have evolved penicillin binding proteins with novel structures. β-lactam antibiotics cannot bind as effectively to these altered PBPs, and, as a result, the β-lactams are less effective at disrupting cell wall
416:
In the absence of β-lactam antibiotics (left), the cell wall plays an important role in bacterial reproduction. Bacteria attempting to grow and divide in the presence of β-lactam antibiotics (right) fail to do so, and instead shed their cell walls, forming osmotically fragile
489:
residue of the PBP active site. This irreversible inhibition of the PBPs prevents the final crosslinking (transpeptidation) of the nascent peptidoglycan layer, disrupting cell wall synthesis. β-lactam antibiotics block not only the division of bacteria, including
193:
biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered,
614:
By definition, all β-lactam antibiotics have a β-lactam ring in their structure. The effectiveness of these antibiotics relies on their ability to reach the PBP intact and their ability to bind to the PBP. Hence, there are two main modes of
1020:
The biosynthesis of the β-lactam ring of tabtoxin mirrors that of the clavams and carbapenems. The closure of the lactam ring in the other monobactams, such as sulfazecin and the nocardicins, may involve a third mechanism involving
722:
ring, and, as such, this structural configuration is critical to their antimicrobial activity. Bacterial resistance to these antibiotics primarily occurs through the production of β-lactamases, enzymes that hydrolyze the
345:
will occur in approximately 0.01% of patients. There is perhaps a 5–10% cross-sensitivity between penicillin-derivatives, cephalosporins, and carbapenems; but this figure has been challenged by various investigators.
952:
To date, two distinct methods of biosynthesizing the β-lactam core of this family of antibiotics have been discovered. The first pathway discovered was that of the penams and cephems. This path begins with a
685:
The production of a β-lactamase by a bacterium does not necessarily rule out all treatment options with β-lactam antibiotics. In some instances, β-lactam antibiotics may be co-administered with a
1448:
Pichichero ME (April 2005). "A review of evidence supporting the
American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients".
1832:
Nangia A, Biradha K, Desiraju GR (1996). "Correlation of biological activity in β-lactam antibiotics with
Woodward and Cohen structural parameters—a Cambridge database study".
349:
Nevertheless, the risk of cross-reactivity is sufficient to warrant the contraindication of all β-lactam antibiotics in patients with a history of severe allergic reactions (
532:
Under normal circumstances, peptidoglycan precursors signal a reorganisation of the bacterial cell wall and, as a consequence, trigger the activation of autolytic cell wall
357:) to any β-lactam antibiotic. Rarely, allergic reactions have been triggered by exposure from kissing and sexual contact with a partner who is taking these antibiotics.
2799:
578:) of the pyramid formed by the nitrogen atom of the β-lactam as the apex and the three adjacent carbon atoms as the base. The second is called "Cohen's parameter",
329:
Immunologically mediated adverse reactions to any β-lactam antibiotic may occur in up to 10% of patients receiving that agent (a small fraction of which are truly
1009:
to the cephem core. As with the penams, the variety of cephalosporins and cephamycins come from different transamidations, as is the case for the penicillins.
2646:"The mechanism for isopenicillin N synthase from density-functional modeling highlights the similarities with other enzymes in the 2-His-1-carboxylate family"
3813:
86:
389:
Penicillin and most other β-lactam antibiotics act by inhibiting penicillin-binding proteins, which normally catalyze cross-linking of bacterial cell walls.
2536:
447:
organisms, being the outermost and primary component of the wall. The final transpeptidation step in the synthesis of the peptidoglycan is facilitated by
2276:
1143:(Report). U.S. Department of Health and Human Services; Food and Drug Administration; Center for Drug Evaluation and Research (CDER). April 2013.
570:
Two structural features of β-lactam antibiotics have been correlated with their antibiotic potency. The first is known as "Woodward's parameter",
473:
residues on the precursor NAM/NAG-peptide subunits of the nascent peptidoglycan layer. The structural similarity between β-lactam antibiotics and
2792:
1691:
Fisher JF, Meroueh SO, Mobashery S (2005). "Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity".
2673:
1059:
745:
458:(PBPs). PBPs vary in their affinity for penicillin and other β-lactam antibiotics. The number of PBPs varies between bacterial species.
2497:
2381:
2301:
2960:
1563:
Miyachiro MM, Contreras-Martel C, Dessen A (2019). "Penicillin-Binding
Proteins (PBPS) and Bacterial Cell Wall Elongation Complexes".
239:
and treatment of bacterial infections caused by susceptible organisms. At first, β-lactam antibiotics were mainly active only against
2785:
1371:"Penetration of drugs through the blood-cerebrospinal fluid/blood-brain barrier for treatment of central nervous system infections"
706:
piperacillin has enhanced its stability against a wide range of β-lactamase enzymes including some
Extended-Spectrum β-lactamases.
544:
Another possibility that has been proposed to account for much of the cytotoxicity of beta lactams focuses on the oxidation of the
2359:
2220:"Characterization of Interactions between CTX-M-15 and Clavulanic Acid, Desfuroylceftiofur, Ceftiofur, Ampicillin, and Nitrocefin"
2754:
Townsend CA, Brown AM, Nguyen LT (1983). "Nocardicin A: stereochemical and biomimetic studies of monocyclic β-lactam formation".
263:
2900:
2889:
1017:. In clavams, the β-lactam is formed prior to the second ring; in carbapenems, the β-lactam ring is closed second in sequence.
17:
4038:
2336:
2122:"Beyond susceptible and resistant Part I: treatment of infections due to Gram-negative organisms with inducible B-lactamases"
1580:
701:(a β-lactamase inhibitor). The clavulanic acid is designed to overwhelm all β-lactamase enzymes, and effectively serve as an
1347:
481:-alanine facilitates their binding to the active site of PBPs. The β-lactam nucleus of the molecule irreversibly binds to (
1006:
822:
2519:
1039:
2537:
https://web.archive.org/web/20240222172948/https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/0550585s063lbl.pdf
1538:
1090:
643:
1144:
1435:
4082:
4055:
1614:"Morphological and ultrastructural changes in bacterial cells as an indicator of antibacterial mechanism of action"
2777:
1914:
Cohen NC (February 1, 1983). ".beta.-Lactam antibiotics: geometrical requirements for antibacterial activities".
1044:
773:
361:
1034:
219:, an enzyme that attacks the β-lactam ring. To overcome this resistance, β-lactam antibiotics can be given with
3957:
3843:
619:
to β-lactams: enzymatic hydrolysis of the β-lactam ring and possession of altered penicillin-binding proteins.
2269:
1669:
1427:
771:
770:
642:
the β-lactam ring of the antibiotic, rendering the antibiotic ineffective. (An example of such an enzyme is
318:
3009:
774:
767:
244:
2169:
Kim D, Kim S, Kwon Y, Kim Y, Park H, Kwak K, Lee H, Lee JH, Jang KM, Kim D, Lee SH, Kang LW (March 2023).
3868:
3788:
2915:
2849:
655:
455:
254:
In uninflamed (normal) brain meninges, the penetration of beta-lactam antibiotics is low, at 0.15 of AUC
553:
552:
could cause cytotoxicity. Bacterial cytotoxicity could arise from incomplete repair of closely spaced
103:
3793:
2920:
944:; the nitrogen atom is position 1, the carbonyl carbon is 2, the α-carbon is 3, and the β-carbon 4.
2816:
1726:
Kasten B, Reski R (January 1, 1997). "β-Lactam antibiotics inhibit chloroplast division in a moss (
986:
768:
750:
646:, discovered in 2009.) The genes encoding these enzymes may be inherently present on the bacterial
616:
548:
nucleotide in the bacterial nucleotide pool. The incorporation of oxidized guanine nucleotide into
311:
212:
115:
3722:
710:
686:
220:
4043:
3858:
3818:
2925:
1132:
Yao, JDC, Moellering, RC Jr. (2007). "Antibacterial agents". In Murray, PR, et al. (eds.).
3882:
3833:
3823:
3578:
3350:
2008:
1014:
772:
354:
248:
3611:
3443:
3262:
2645:
4087:
3863:
3848:
3828:
1064:
280:
236:
754:. Altered PBPs do not necessarily rule out all treatment options with β-lactam antibiotics.
3947:
3853:
3798:
2708:
2411:
1872:
1785:
1774:"Oxidation of the guanine nucleotide pool underlies cell death by bactericidal antibiotics"
1743:
1450:
1283:
954:
769:
522:
338:
8:
3838:
3808:
3657:
3619:
766:
702:
443:. The peptidoglycan layer is important for cell wall structural integrity, especially in
432:
2712:
2415:
1876:
1789:
1747:
1648:
1287:
2484:
2432:
2399:
2355:
2328:
2246:
2219:
2195:
2170:
2146:
2121:
2097:
2064:
2045:
1983:
1958:
1806:
1773:
1661:
1594:
1530:
1475:
1395:
1370:
1304:
1267:
1243:
1210:
1191:
200:
2586:
2549:
2460:"Stability of Meropenem After Reconstitution for Administration by Prolonged Infusion"
2317:"Laboratory Diagnosis of Infection Due to Bacteria, Fungi, Parasites, and Rickettsiae"
1755:
3373:
3079:
2854:
2736:
2731:
2696:
2665:
2626:
2591:
2489:
2437:
2423:
2375:
2332:
2316:
2295:
2251:
2200:
2151:
2102:
2084:
2037:
2029:
1988:
1939:
1931:
1896:
1888:
1845:
1811:
1708:
1653:
1598:
1586:
1576:
1522:
1514:
1467:
1431:
1400:
1339:
1309:
1248:
1183:
1141:
Non-Penicillin Beta Lactam Drugs: A CGMP Framework for
Preventing Cross-Contamination
1102:
982:
448:
98:
2577:
2049:
1534:
1479:
1234:
1195:
407:
50:
3961:
3112:
2910:
2807:
2763:
2726:
2716:
2657:
2618:
2581:
2573:
2479:
2471:
2427:
2419:
2324:
2241:
2231:
2190:
2182:
2141:
2133:
2092:
2076:
2021:
1978:
1970:
1923:
1880:
1837:
1801:
1793:
1751:
1700:
1665:
1643:
1633:
1625:
1568:
1506:
1459:
1390:
1382:
1299:
1291:
1238:
1230:
1175:
1022:
330:
565:
3749:
3193:
3020:
1510:
698:
669:
659:
590:. This distance is thought to correspond to the distance between the carboxylate-
299:
224:
121:
2824:
2820:
2186:
1865:
Philosophical
Transactions of the Royal Society of London B: Biological Sciences
1572:
1331:
714:
develop tailored boronic acids to target different isozymes of beta-lactamases.
4049:
2979:
2701:
Proceedings of the
National Academy of Sciences of the United States of America
1295:
990:
958:
631:
518:
495:
288:
216:
2622:
2137:
1629:
1272:
isolate (IMI 15378) reveals sequence divergence of penicillin synthesis genes"
1179:
4076:
3943:
3802:
3417:
3245:
3157:
3151:
3097:
3093:
3063:
3058:
3053:
3048:
3038:
2974:
2945:
2935:
2523:
2475:
2088:
2033:
2025:
2006:
Gin A, Dilay L, Karlowsky JA, Walkty A, Rubinstein E, Zhanel GG (June 2007).
1935:
1892:
1849:
1518:
996:
635:
595:
491:
444:
436:
240:
166:
91:
60:
2721:
1797:
1110:
3712:
3629:
3472:
3330:
3315:
3121:
2950:
2669:
2630:
2493:
2459:
2441:
2255:
2204:
2155:
2106:
2041:
1992:
1884:
1815:
1712:
1657:
1590:
1526:
1494:
1471:
1463:
1404:
1343:
1313:
1252:
1187:
1140:
1106:
829:
591:
428:
2740:
2595:
1943:
1900:
1266:
Pathak A, Nowell RW, Wilson CG, Ryan MJ, Barraclough TG (September 2020).
1005:
The biosynthesis of cephems branch off at isopenicillin N by an oxidative
4024:
4002:
3971:
3965:
3891:
3771:
3761:
3647:
3639:
3624:
3538:
3508:
3503:
3498:
3493:
3488:
3467:
3456:
3428:
3422:
3378:
3340:
3320:
3305:
3253:
3131:
3088:
3029:
2995:
2970:
2940:
2930:
2808:
2236:
1974:
1841:
1772:
Foti JJ, Devadoss B, Winkler JA, Collins JJ, Walker GC (April 20, 2012).
1386:
909:
851:
840:
737:
694:
679:
583:
506:
502:
418:
365:
342:
292:
186:
154:
3899:
Insert into bacterial cell wall causing perforation and depolarization:
2767:
1927:
1493:
Liccardi G, Caminati M, Senna G, Calzetta L, Rogliani P (October 2017).
385:
64:
4012:
4007:
3975:
3951:
3922:
3900:
3766:
3739:
3689:
3670:
3601:
3591:
3553:
3543:
3533:
3518:
3513:
3461:
3432:
3398:
3388:
3368:
3325:
3295:
3290:
3280:
3249:
3175:
3147:
3126:
3102:
3043:
3034:
2875:
2009:"Piperacillin–tazobactam: a β-lactam/β-lactamase inhibitor combination"
1069:
962:
929:
882:
844:
723:
647:
639:
470:
307:
195:
182:
178:
170:
158:
150:
56:
41:
2661:
2080:
1704:
1638:
134:
4019:
3905:
3756:
3734:
3707:
3702:
3697:
3675:
3665:
3596:
3567:
3558:
3528:
3483:
3407:
3402:
3393:
3383:
3363:
3335:
3310:
3300:
3285:
3275:
3270:
3230:
3225:
3218:
3207:
3197:
3188:
3069:
2990:
2985:
2812:
1054:
920:
690:
533:
526:
510:
498:
482:
440:
350:
284:
190:
1166:
Elander RP (2003). "Industrial production of β-lactam antibiotics".
730:
3995:
3586:
3562:
3548:
3523:
3478:
3451:
3412:
3358:
3213:
3202:
1613:
1049:
905:
894:
867:
587:
575:
369:
303:
2458:
Fawaz S, Barton S, Whitney L, Swinden J, Nabhani-Gebara S (2019).
817:β-lactams are classified according to their core ring structures.
665:
398:
916:
878:
651:
545:
514:
334:
3745:
3241:
2547:
2218:
Ahmadvand P, Avillan JJ, Lewis JA, Call DR, Kang C (May 2022).
1562:
898:
855:
736:
synthesis. Notable examples of this mode of resistance include
628:
317:
Pain and inflammation at the injection site is also common for
174:
675:
598:
of the PBP enzyme. The best antibiotics are those with higher
3730:
3179:
2879:
1863:
Woodward RB (May 16, 1980). "Penems and related substances".
1492:
978:
941:
871:
833:
283:
for the β-lactam antibiotics include diarrhea, nausea, rash,
162:
1567:. Subcellular Biochemistry. Vol. 93. pp. 273–289.
622:
266:
of cerebrosopinal fluid against area under curve of serum).
63:(bottom) the 2 most common groups of β-lactam antibiotics .
2609:
Dalhoff A, Janjic N, Echols R (2006). "Redefining penems".
1565:
Macromolecular
Protein Complexes II: Structure and Function
1771:
1131:
2457:
2217:
1611:
1091:"Appropriate prescribing of oral beta-lactam antibiotics"
549:
2643:
2065:"Class D β-Lactamases: a reappraisal after five decades"
2321:
Principles and
Practice of Pediatric Infectious Disease
2005:
556:
lesions in the DNA resulting in double-strand breaks.
2548:
Ubukata K, Nonoguchi R, Matsuhashi M, Konno M (1989).
2063:
Leonard DA, Bonomo RA, Powers RA (November 19, 2013).
1834:
Journal of the
Chemical Society, Perkin Transactions 2
1690:
1268:"Comparative genomics of Alexander Fleming's original
1265:
1208:
3814:
Benzathine benzylpenicillin/procaine benzylpenicillin
1831:
1040:
ATC code J01C Beta-lactam antibacterials, penicillins
582:, and is the distance between the carbon atom of the
2314:
863:β-lactams fused to unsaturated five-membered rings:
380:
2753:
2608:
2062:
890:β-lactams fused to unsaturated six-membered rings:
2694:
2350:
2348:
2126:Journal of Pediatric Pharmacology and Therapeutics
2007:
1499:Current Opinion in Allergy and Clinical Immunology
981:cyclized (two cyclizations by a single enzyme) to
989:(IPNS) to form the penam core structure. Various
940:The numbering of monobactams follows that of the
731:Possession of altered penicillin-binding proteins
4074:
2697:"β-lactam synthetase: a new biosynthetic enzyme"
1368:
928:β-lactams not fused to any other ring are named
157:ring in their chemical structure. This includes
2453:
2451:
2393:
2391:
2345:
1558:
1556:
765:
602:values (more reactive to hydrolysis) and lower
189:. Most β-lactam antibiotics work by inhibiting
2171:"Structural Insights for β-Lactam Antibiotics"
1827:
1825:
1329:
1325:
1323:
1211:"Fleming's penicillin producing strain is not
1045:ATC code J01D Other beta-lactam antibacterials
2793:
2168:
1447:
2644:Lundberg M, Siegbahn PE, Morokuma K (2008).
2558:gene, which encodes a methicillin-resistant
2448:
2400:"Metallo-β-lactamase structure and function"
2388:
2211:
2162:
2119:
1605:
1553:
1088:
2541:
1956:
1822:
1767:
1765:
1725:
1612:Cushnie TP, O'Driscoll NH, Lamb AJ (2016).
1369:Nau R, Sörgel F, Eiffert H (October 2010).
1362:
1320:
1259:
1209:Houbraken J, Frisvad JC, Samson RA (2011).
1202:
1136:(9th ed.). Washington D.C.: ASM Press.
1082:
1060:Discovery and development of cephalosporins
993:lead to the different natural penicillins.
324:
235:β-lactam antibiotics are indicated for the
2800:
2786:
513:. In contrast, they have no effect on the
494:, but also the division of cyanelles, the
251:organisms has increased their usefulness.
215:to β-lactam antibiotics by synthesizing a
49:
3921:Inhibits PG elongation and crosslinking:
2730:
2720:
2585:
2483:
2431:
2245:
2235:
2194:
2145:
2096:
1982:
1959:"Three decades of β-lactamase inhibitors"
1805:
1647:
1637:
1394:
1303:
1242:
662:may be induced by exposure to β-lactams.
623:Enzymatic hydrolysis of the β-lactam ring
274:
2756:Journal of the American Chemical Society
2397:
1862:
1762:
995:
915:β-lactams containing 3,6-dihydro-2H-1,3-
893:β-lactams containing 3,6-dihydro-2H-1,3-
761:
674:
664:
384:
243:bacteria, yet the recent development of
2695:Bachmann BO, Li R, Townsend CA (1998).
2676:from the original on September 22, 2017
2014:Expert Review of Anti-infective Therapy
1418:
1416:
1414:
1165:
904:β-lactams containing 1,2,3,4-tetrahydro
364:may occur after initial treatment of a
14:
4075:
2500:from the original on February 27, 2024
2380:: CS1 maint: archived copy as title (
2362:from the original on February 22, 2024
2300:: CS1 maint: archived copy as title (
2282:from the original on February 16, 2022
1350:from the original on December 15, 2020
1168:Applied Microbiology and Biotechnology
1147:from the original on December 13, 2019
609:
461:β-lactam antibiotics are analogues of
375:
2781:
2562:-specific penicillin-binding protein"
2323:. W.B. Saunders. pp. 1341–1352.
2315:Christenson JC, Korgenski EK (2008).
1913:
1672:from the original on October 7, 2017
1618:Cellular and Molecular Life Sciences
1495:"Anaphylaxis and intimate behaviour"
1411:
1089:Holten KB, Onusko EM (August 2000).
877:β-lactams containing 2,3-dihydro-1H-
586:and the oxygen atom of the β-lactam
539:
529:of plastid division in land plants.
1541:from the original on April 25, 2023
961:(ACVS), which generates the linear
435:by inhibiting the synthesis of the
321:administered β-lactam antibiotics.
247:antibiotics active against various
27:Class of broad-spectrum antibiotics
24:
2329:10.1016/B978-0-7020-3468-8.50292-3
1424:Australian Medicines Handbook 2004
644:New Delhi metallo-beta-lactamase 1
269:
25:
4099:
3946:subunit synthesis and transport:
606:values (better binding to PBPs).
381:Inhibition of cell wall synthesis
2550:"Expression and inducibility in
2424:10.1111/j.1749-6632.2012.06796.x
985:intermediate isopenicillin N by
866:β-lactams containing 2,3-dihydro
406:
397:
198:, was isolated from a strain of
2747:
2688:
2637:
2602:
2578:10.1128/jb.171.5.2882-2885.1989
2530:
2512:
2308:
2262:
2113:
2056:
1999:
1950:
1907:
1856:
1719:
1684:
1486:
1235:10.5598/imafungus.2011.02.01.12
1134:Manual of Clinical Microbiology
955:nonribosomal peptide synthetase
947:
757:
3844:Imipenem/cilastatin/relebactam
1916:Journal of Medicinal Chemistry
1441:
1159:
1125:
777:The β-lactam core structures.
627:If the bacterium produces the
230:
13:
1:
2520:"Ceftriaxone: Package Insert"
2069:Accounts of Chemical Research
1963:Clinical Microbiology Reviews
1756:10.1016/S0176-1617(97)80193-9
1428:Australian Medicines Handbook
1375:Clinical Microbiology Reviews
1330:Pandey N, Cascella M (2020).
1075:
854:rings are named oxapenams or
1957:Drawz SM, Bonomo RA (2010).
1511:10.1097/ACI.0000000000000386
1035:List of β-lactam antibiotics
697:(a β-lactam antibiotic) and
372:with a β-lactam antibiotic.
7:
3869:Ticarcillin/clavulanic acid
3789:Amoxicillin/clavulanic acid
2926:Phenoxymethylpenicillin (V)
2916:Benzathine benzylpenicillin
2398:Palzkill T (January 2013).
2187:10.4062/biomolther.2023.008
1736:Journal of Plant Physiology
1573:10.1007/978-3-030-28151-9_8
1155:– via US FDA website.
1028:
1013:substrates is activated by
748:) and penicillin-resistant
656:plasmid-mediated resistance
456:penicillin binding proteins
362:Jarisch–Herxheimer reaction
10:
4104:
1296:10.1038/s41598-020-72584-5
1023:inversion of configuration
563:
559:
104:Penicillin binding protein
4033:
3985:
3935:
3914:
3890:
3881:
3794:Ampicillin/flucloxacillin
3781:
3721:
3688:
3656:
3638:
3610:
3577:
3442:
3349:
3261:
3240:
3174:
3140:
3111:
3078:
3019:
3008:
2959:
2921:Procaine benzylpenicillin
2899:
2888:
2874:
2832:
2623:10.1016/j.bcp.2005.12.003
2138:10.5863/1551-6776-16.1.23
1630:10.1007/s00018-016-2302-2
1332:"Beta lactam antibiotics"
1180:10.1007/s00253-003-1274-y
1095:American Family Physician
521:. This is supporting the
427:β-lactam antibiotics are
302:include fever, vomiting,
133:
128:
114:
109:
97:
85:
77:
72:
48:
39:
34:
2611:Biochemical Pharmacology
2476:10.1177/0018578718779009
2026:10.1586/14787210.5.3.365
987:isopenicillin N synthase
751:Streptococcus pneumoniae
574:, and is the height (in
517:of the highly developed
325:Allergy/hypersensitivity
312:pseudomembranous colitis
4083:Beta-lactam antibiotics
3859:Piperacillin/tazobactam
3819:Cefepime/enmetazobactam
2722:10.1073/pnas.95.16.9082
2566:Journal of Bacteriology
1798:10.1126/science.1219192
1732:Lycopersicon esculentum
1213:Penicillium chrysogenum
650:or may be acquired via
554:8-oxo-2'-deoxyguanosine
245:broad-spectrum β-lactam
211:Bacteria often develop
147:beta-lactam antibiotics
3950:synthesis inhibition (
3834:Ceftolozane/tazobactam
3824:Cefoperazone/sulbactam
3723:β-lactamase inhibitors
1885:10.1098/rstb.1980.0042
1464:10.1542/peds.2004-1276
1422:Rossi S (ed.) (2004).
1002:
977:-valine (ACV). ACV is
814:
711:β-lactamase inhibitors
682:
672:
505:, and the division of
469:-alanine—the terminal
390:
355:interstitial nephritis
281:adverse drug reactions
275:Adverse drug reactions
221:β-lactamase inhibitors
18:Beta-lactam antibiotic
3864:Sulbactam/durlobactam
3849:Meropenem/vaborbactam
3829:Ceftazidime/avibactam
2961:β-lactamase resistant
2901:β-lactamase sensitive
2552:Staphylococcus aureus
2120:Macdougall C (2011).
1730:) but not in tomato (
1728:Physcomitrella patens
1065:History of penicillin
999:
839:β-lactams containing
828:β-lactams containing
825:five-membered rings:
776:
742:Staphylococcus aureus
687:β-lactamase inhibitor
678:
668:
388:
3854:Panipenem/betamipron
3799:Ampicillin/sulbactam
2911:Benzylpenicillin (G)
2845:cell wall by binding
2237:10.3390/ijms23095229
1975:10.1128/CMR.00037-09
1842:10.1039/p29960000943
1387:10.1128/CMR.00007-10
1282:(1): Article 15705.
1001:method (fourth row).
617:bacterial resistance
523:endosymbiotic theory
262:ratio (the ratio of
143:β-lactam antibiotics
3839:Imipenem/cilastatin
3809:Aztreonam/avibactam
3620:Ceftaroline fosamil
2768:10.1021/ja00342a047
2713:1998PNAS...95.9082B
2416:2013NYASA1277...91P
2175:Biomol Ther (Seoul)
1928:10.1021/jm00356a027
1877:1980RSPTB.289..239W
1790:2012Sci...336..315F
1748:1997JPPhy.150..137K
1288:2020NatSR..1015705P
850:β-lactams fused to
821:β-lactams fused to
658:), and β-lactamase
610:Modes of resistance
566:β-lactam reactivity
439:layer of bacterial
376:Mechanism of action
206:Penicillium notatum
81:Bacterial infection
35:β-lactam antibiotic
4060:Never to phase III
3992:Hydrolyze NAM-NAG
3080:Carboxypenicillins
2843:layer of bacterial
2839:(inhibit synthesis
1276:Scientific Reports
1003:
815:
683:
673:
638:, the enzyme will
391:
368:infection such as
201:Penicillium rubens
55:Core structure of
4070:
4069:
3931:
3930:
3877:
3876:
3684:
3683:
3466:Antipseudomonal (
3374:Cefuroxime axetil
3170:
3169:
3166:
3165:
3113:Ureidopenicillins
3004:
3003:
2868:
2861:
2857:
2847:to and inhibiting
2707:(16): 9082–9086.
2662:10.1021/bi701577q
2526:on April 2, 2023.
2464:Hospital Pharmacy
2338:978-0-7020-3468-8
2081:10.1021/ar300327a
2075:(11): 2407–2415.
1871:(1036): 239–250.
1784:(6079): 315–319.
1705:10.1021/cr030102i
1624:(23): 4471–4492.
1582:978-3-030-28150-2
1025:at the β-carbon.
976:
972:
968:
693:(FGP) is made of
540:Guanine oxidation
525:and indicates an
451:
140:
139:
99:Biological target
73:Class identifiers
16:(Redirected from
4095:
3888:
3887:
3259:
3258:
3115:(4th generation)
3082:(4th generation)
3023:(3rd generation)
3021:Aminopenicillins
3017:
3016:
2964:(2nd generation)
2904:(1st generation)
2897:
2896:
2886:
2885:
2872:
2871:
2867:
2859:
2855:
2841:of peptidoglycan
2837:
2802:
2795:
2788:
2779:
2778:
2772:
2771:
2751:
2745:
2744:
2734:
2724:
2692:
2686:
2685:
2683:
2681:
2656:(3): 1031–1042.
2641:
2635:
2634:
2617:(7): 1085–1095.
2606:
2600:
2599:
2589:
2545:
2539:
2534:
2528:
2527:
2522:. Archived from
2516:
2510:
2509:
2507:
2505:
2487:
2455:
2446:
2445:
2435:
2404:Ann N Y Acad Sci
2395:
2386:
2385:
2379:
2371:
2369:
2367:
2352:
2343:
2342:
2312:
2306:
2305:
2299:
2291:
2289:
2287:
2281:
2274:
2266:
2260:
2259:
2249:
2239:
2215:
2209:
2208:
2198:
2166:
2160:
2159:
2149:
2117:
2111:
2110:
2100:
2060:
2054:
2053:
2011:
2003:
1997:
1996:
1986:
1954:
1948:
1947:
1911:
1905:
1904:
1860:
1854:
1853:
1829:
1820:
1819:
1809:
1769:
1760:
1759:
1723:
1717:
1716:
1693:Chemical Reviews
1688:
1682:
1681:
1679:
1677:
1651:
1641:
1609:
1603:
1602:
1560:
1551:
1550:
1548:
1546:
1490:
1484:
1483:
1445:
1439:
1420:
1409:
1408:
1398:
1366:
1360:
1359:
1357:
1355:
1327:
1318:
1317:
1307:
1263:
1257:
1256:
1246:
1206:
1200:
1199:
1174:(5–6): 385–392.
1163:
1157:
1156:
1154:
1152:
1137:
1129:
1123:
1122:
1120:
1118:
1109:. Archived from
1086:
974:
970:
969:-α-aminoadipyl)-
966:
919:rings are named
908:rings are named
897:rings are named
881:rings are named
870:rings are named
843:rings are named
832:rings are named
764:
480:
476:
468:
464:
454:, also known as
452:-transpeptidases
449:
410:
401:
339:amoxicillin rash
264:area under curve
124:
53:
32:
31:
21:
4103:
4102:
4098:
4097:
4096:
4094:
4093:
4092:
4073:
4072:
4071:
4066:
4065:
4050:Clinical trials
4029:
3981:
3927:
3910:
3873:
3777:
3750:Clavulanic acid
3717:
3680:
3652:
3634:
3606:
3573:
3438:
3345:
3252:
3248:
3244:
3236:
3194:Antipseudomonal
3162:
3136:
3107:
3074:
3011:
3000:
2963:
2955:
2903:
2891:
2864:transpeptidases
2863:
2853:
2848:
2846:
2844:
2842:
2840:
2838:
2836:
2828:
2806:
2776:
2775:
2752:
2748:
2693:
2689:
2679:
2677:
2642:
2638:
2607:
2603:
2546:
2542:
2535:
2531:
2518:
2517:
2513:
2503:
2501:
2456:
2449:
2396:
2389:
2373:
2372:
2365:
2363:
2356:"Archived copy"
2354:
2353:
2346:
2339:
2313:
2309:
2293:
2292:
2285:
2283:
2279:
2272:
2270:"Archived copy"
2268:
2267:
2263:
2216:
2212:
2167:
2163:
2118:
2114:
2061:
2057:
2004:
2000:
1955:
1951:
1912:
1908:
1861:
1857:
1830:
1823:
1770:
1763:
1724:
1720:
1689:
1685:
1675:
1673:
1610:
1606:
1583:
1561:
1554:
1544:
1542:
1491:
1487:
1446:
1442:
1421:
1412:
1367:
1363:
1353:
1351:
1328:
1321:
1264:
1260:
1207:
1203:
1164:
1160:
1150:
1148:
1139:
1130:
1126:
1116:
1114:
1113:on June 6, 2011
1087:
1083:
1078:
1031:
991:transamidations
950:
809:A carbacephem.
775:
762:
760:
733:
699:clavulanic acid
689:. For example,
670:Clavulanic acid
660:gene expression
625:
612:
568:
562:
542:
519:vascular plants
488:
478:
474:
466:
462:
425:
424:
423:
422:
413:
412:
411:
403:
402:
383:
378:
353:, anaphylaxis,
337:reactions, see
327:
300:adverse effects
277:
272:
270:Adverse effects
261:
257:
233:
225:clavulanic acid
153:that contain a
120:
68:
28:
23:
22:
15:
12:
11:
5:
4101:
4091:
4090:
4085:
4068:
4067:
4064:
4063:
4062:
4061:
4058:
4047:
4041:
4035:
4034:
4031:
4030:
4028:
4027:
4022:
4017:
4016:
4015:
4010:
4000:
3999:
3998:
3989:
3987:
3983:
3982:
3980:
3979:
3969:
3955:
3939:
3937:
3933:
3932:
3929:
3928:
3926:
3925:
3918:
3916:
3912:
3911:
3909:
3908:
3903:
3896:
3894:
3885:
3879:
3878:
3875:
3874:
3872:
3871:
3866:
3861:
3856:
3851:
3846:
3841:
3836:
3831:
3826:
3821:
3816:
3811:
3806:
3796:
3791:
3785:
3783:
3779:
3778:
3776:
3775:
3769:
3764:
3759:
3755:non-β-lactam (
3753:
3743:
3737:
3727:
3725:
3719:
3718:
3716:
3715:
3710:
3705:
3700:
3694:
3692:
3686:
3685:
3682:
3681:
3679:
3678:
3673:
3668:
3662:
3660:
3654:
3653:
3651:
3650:
3644:
3642:
3636:
3635:
3633:
3632:
3627:
3622:
3616:
3614:
3612:5th generation
3608:
3607:
3605:
3604:
3599:
3594:
3589:
3583:
3581:
3579:4th generation
3575:
3574:
3572:
3571:
3565:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3470:
3464:
3459:
3454:
3448:
3446:
3444:3rd generation
3440:
3439:
3437:
3436:
3426:
3420:
3415:
3410:
3405:
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3355:
3353:
3351:2nd generation
3347:
3346:
3344:
3343:
3338:
3333:
3328:
3323:
3318:
3313:
3308:
3303:
3298:
3293:
3288:
3283:
3278:
3273:
3267:
3265:
3263:1st generation
3256:
3246:Cephalosporins
3238:
3237:
3235:
3234:
3228:
3222:
3216:
3211:
3205:
3200:
3191:
3184:
3182:
3172:
3171:
3168:
3167:
3164:
3163:
3161:
3160:
3155:
3144:
3142:
3138:
3137:
3135:
3134:
3129:
3124:
3118:
3116:
3109:
3108:
3106:
3105:
3100:
3091:
3085:
3083:
3076:
3075:
3073:
3072:
3067:
3061:
3056:
3051:
3046:
3041:
3032:
3026:
3024:
3014:
3006:
3005:
3002:
3001:
2999:
2998:
2993:
2988:
2983:
2980:Flucloxacillin
2977:
2967:
2965:
2957:
2956:
2954:
2953:
2948:
2943:
2938:
2933:
2928:
2923:
2918:
2913:
2907:
2905:
2894:
2883:
2869:
2830:
2829:
2811:active on the
2809:Antibacterials
2805:
2804:
2797:
2790:
2782:
2774:
2773:
2762:(4): 919–927.
2746:
2687:
2636:
2601:
2540:
2529:
2511:
2470:(3): 190–196.
2447:
2387:
2344:
2337:
2307:
2261:
2210:
2181:(2): 141–147.
2161:
2112:
2055:
2020:(3): 365–383.
1998:
1969:(1): 160–201.
1949:
1922:(2): 259–264.
1906:
1855:
1836:(5): 943–953.
1821:
1761:
1742:(1): 137–140.
1718:
1699:(2): 395–424.
1683:
1604:
1581:
1552:
1505:(5): 350–355.
1485:
1458:(4): 1048–57.
1440:
1410:
1361:
1319:
1258:
1201:
1158:
1124:
1080:
1079:
1077:
1074:
1073:
1072:
1067:
1062:
1057:
1052:
1047:
1042:
1037:
1030:
1027:
1007:ring expansion
959:ACV synthetase
949:
946:
934:
933:
926:
925:
924:
913:
902:
888:
887:
886:
875:
861:
860:
859:
848:
837:
801:A monobactam.
797:A carbapenem.
785:A carbapenam.
759:
756:
732:
729:
634:or the enzyme
624:
621:
611:
608:
561:
558:
541:
538:
496:photosynthetic
486:
415:
414:
405:
404:
396:
395:
394:
393:
392:
382:
379:
377:
374:
326:
323:
306:, dermatitis,
289:superinfection
276:
273:
271:
268:
259:
255:
232:
229:
208:at the time).
167:cephalosporins
138:
137:
131:
130:
126:
125:
118:
112:
111:
110:External links
107:
106:
101:
95:
94:
89:
83:
82:
79:
75:
74:
70:
69:
61:cephalosporins
54:
46:
45:
37:
36:
26:
9:
6:
4:
3:
2:
4100:
4089:
4086:
4084:
4081:
4080:
4078:
4059:
4057:
4054:
4053:
4051:
4048:
4045:
4042:
4040:
4037:
4036:
4032:
4026:
4023:
4021:
4018:
4014:
4011:
4009:
4006:
4005:
4004:
4001:
3997:
3994:
3993:
3991:
3990:
3988:
3984:
3977:
3973:
3970:
3967:
3963:
3959:
3956:
3953:
3949:
3945:
3941:
3940:
3938:
3936:Intracellular
3934:
3924:
3920:
3919:
3917:
3913:
3907:
3904:
3902:
3898:
3897:
3895:
3893:
3889:
3886:
3884:
3880:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3804:
3803:Sultamicillin
3800:
3797:
3795:
3792:
3790:
3787:
3786:
3784:
3780:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3754:
3751:
3747:
3744:
3741:
3738:
3736:
3732:
3729:
3728:
3726:
3724:
3720:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3695:
3693:
3691:
3687:
3677:
3674:
3672:
3669:
3667:
3664:
3663:
3661:
3659:
3655:
3649:
3646:
3645:
3643:
3641:
3637:
3631:
3628:
3626:
3623:
3621:
3618:
3617:
3615:
3613:
3609:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3584:
3582:
3580:
3576:
3569:
3566:
3564:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3474:
3471:
3469:
3465:
3463:
3460:
3458:
3455:
3453:
3450:
3449:
3447:
3445:
3441:
3434:
3430:
3427:
3424:
3421:
3419:
3418:Cefbuperazone
3416:
3414:
3411:
3409:
3406:
3404:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3356:
3354:
3352:
3348:
3342:
3339:
3337:
3334:
3332:
3329:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3269:
3268:
3266:
3264:
3260:
3257:
3255:
3251:
3247:
3243:
3239:
3232:
3229:
3227:
3223:
3220:
3217:
3215:
3212:
3209:
3206:
3204:
3201:
3199:
3195:
3192:
3190:
3187:Carbapenems (
3186:
3185:
3183:
3181:
3177:
3173:
3159:
3158:Sulbenicillin
3156:
3153:
3152:Pivmecillinam
3149:
3146:
3145:
3143:
3139:
3133:
3130:
3128:
3125:
3123:
3120:
3119:
3117:
3114:
3110:
3104:
3101:
3099:
3098:Carindacillin
3095:
3094:Carbenicillin
3092:
3090:
3087:
3086:
3084:
3081:
3077:
3071:
3068:
3065:
3064:Talampicillin
3062:
3060:
3059:Metampicillin
3057:
3055:
3054:Lenampicillin
3052:
3050:
3049:Bacampicillin
3047:
3045:
3042:
3040:
3039:Pivampicillin
3036:
3033:
3031:
3028:
3027:
3025:
3022:
3018:
3015:
3013:
3007:
2997:
2994:
2992:
2989:
2987:
2984:
2981:
2978:
2976:
2975:Dicloxacillin
2972:
2969:
2968:
2966:
2962:
2958:
2952:
2949:
2947:
2946:Clometocillin
2944:
2942:
2939:
2937:
2936:Pheneticillin
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2908:
2906:
2902:
2898:
2895:
2893:
2887:
2884:
2881:
2877:
2873:
2870:
2865:
2851:
2835:
2831:
2826:
2822:
2818:
2814:
2810:
2803:
2798:
2796:
2791:
2789:
2784:
2783:
2780:
2769:
2765:
2761:
2757:
2750:
2742:
2738:
2733:
2728:
2723:
2718:
2714:
2710:
2706:
2702:
2698:
2691:
2675:
2671:
2667:
2663:
2659:
2655:
2651:
2647:
2640:
2632:
2628:
2624:
2620:
2616:
2612:
2605:
2597:
2593:
2588:
2583:
2579:
2575:
2572:(5): 2882–5.
2571:
2567:
2563:
2561:
2557:
2553:
2544:
2538:
2533:
2525:
2521:
2515:
2499:
2495:
2491:
2486:
2481:
2477:
2473:
2469:
2465:
2461:
2454:
2452:
2443:
2439:
2434:
2429:
2425:
2421:
2417:
2413:
2410:(1): 91–104.
2409:
2405:
2401:
2394:
2392:
2383:
2377:
2361:
2357:
2351:
2349:
2340:
2334:
2330:
2326:
2322:
2318:
2311:
2303:
2297:
2278:
2271:
2265:
2257:
2253:
2248:
2243:
2238:
2233:
2229:
2225:
2224:Int J Mol Sci
2221:
2214:
2206:
2202:
2197:
2192:
2188:
2184:
2180:
2176:
2172:
2165:
2157:
2153:
2148:
2143:
2139:
2135:
2131:
2127:
2123:
2116:
2108:
2104:
2099:
2094:
2090:
2086:
2082:
2078:
2074:
2070:
2066:
2059:
2051:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2015:
2010:
2002:
1994:
1990:
1985:
1980:
1976:
1972:
1968:
1964:
1960:
1953:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1910:
1902:
1898:
1894:
1890:
1886:
1882:
1878:
1874:
1870:
1866:
1859:
1851:
1847:
1843:
1839:
1835:
1828:
1826:
1817:
1813:
1808:
1803:
1799:
1795:
1791:
1787:
1783:
1779:
1775:
1768:
1766:
1757:
1753:
1749:
1745:
1741:
1737:
1733:
1729:
1722:
1714:
1710:
1706:
1702:
1698:
1694:
1687:
1671:
1667:
1663:
1659:
1655:
1650:
1645:
1640:
1635:
1631:
1627:
1623:
1619:
1615:
1608:
1600:
1596:
1592:
1588:
1584:
1578:
1574:
1570:
1566:
1559:
1557:
1540:
1536:
1532:
1528:
1524:
1520:
1516:
1512:
1508:
1504:
1500:
1496:
1489:
1481:
1477:
1473:
1469:
1465:
1461:
1457:
1453:
1452:
1444:
1437:
1436:0-9578521-4-2
1433:
1429:
1425:
1419:
1417:
1415:
1406:
1402:
1397:
1392:
1388:
1384:
1381:(4): 858–83.
1380:
1376:
1372:
1365:
1349:
1345:
1341:
1337:
1333:
1326:
1324:
1315:
1311:
1306:
1301:
1297:
1293:
1289:
1285:
1281:
1277:
1273:
1271:
1262:
1254:
1250:
1245:
1240:
1236:
1232:
1228:
1224:
1220:
1218:
1214:
1205:
1197:
1193:
1189:
1185:
1181:
1177:
1173:
1169:
1162:
1146:
1142:
1135:
1128:
1112:
1108:
1104:
1101:(3): 611–20.
1100:
1096:
1092:
1085:
1081:
1071:
1068:
1066:
1063:
1061:
1058:
1056:
1053:
1051:
1048:
1046:
1043:
1041:
1038:
1036:
1033:
1032:
1026:
1024:
1018:
1016:
1010:
1008:
998:
994:
992:
988:
984:
980:
964:
960:
956:
945:
943:
938:
931:
927:
922:
918:
914:
911:
907:
903:
900:
896:
892:
891:
889:
884:
880:
876:
873:
869:
865:
864:
862:
857:
853:
849:
846:
842:
838:
835:
831:
827:
826:
824:
820:
819:
818:
813:An oxacephem.
812:
808:
804:
800:
796:
792:
789:An oxapenam.
788:
784:
780:
755:
753:
752:
747:
743:
739:
728:
725:
719:
715:
712:
707:
704:
700:
696:
692:
688:
681:
677:
671:
667:
663:
661:
657:
653:
649:
645:
641:
637:
636:penicillinase
633:
630:
620:
618:
607:
605:
601:
597:
596:oxyanion hole
593:
589:
585:
581:
577:
573:
567:
557:
555:
551:
547:
537:
535:
530:
528:
524:
520:
516:
512:
508:
504:
500:
497:
493:
492:cyanobacteria
484:
472:
459:
457:
453:
446:
445:gram-positive
442:
438:
437:peptidoglycan
434:
430:
420:
409:
400:
387:
373:
371:
367:
363:
358:
356:
352:
347:
344:
340:
336:
332:
322:
320:
315:
313:
309:
305:
301:
296:
294:
290:
286:
282:
267:
265:
252:
250:
249:gram-negative
246:
242:
241:gram-positive
238:
228:
226:
222:
218:
214:
209:
207:
203:
202:
197:
192:
188:
184:
180:
176:
172:
168:
164:
161:derivatives (
160:
156:
152:
148:
144:
136:
132:
127:
123:
119:
117:
113:
108:
105:
102:
100:
96:
93:
90:
88:
84:
80:
76:
71:
66:
62:
58:
52:
47:
44:
43:
38:
33:
30:
19:
4088:Nephrotoxins
3974:inhibitors (
3964:inhibitors (
3892:Lipopeptides
3883:Polypeptides
3782:Combinations
3713:Nocardicin A
3630:Ceftobiprole
3473:Cefoperazone
3331:Cefaloridine
3316:Cefaloglycin
3254:Carbacephems
3122:Piperacillin
2951:Penamecillin
2852:, a group of
2833:
2759:
2755:
2749:
2704:
2700:
2690:
2678:. Retrieved
2653:
2650:Biochemistry
2649:
2639:
2614:
2610:
2604:
2569:
2565:
2559:
2555:
2551:
2543:
2532:
2524:the original
2514:
2504:February 22,
2502:. Retrieved
2467:
2463:
2407:
2403:
2366:February 22,
2364:. Retrieved
2320:
2310:
2286:February 22,
2284:. Retrieved
2264:
2227:
2223:
2213:
2178:
2174:
2164:
2132:(1): 23–30.
2129:
2125:
2115:
2072:
2068:
2058:
2017:
2013:
2001:
1966:
1962:
1952:
1919:
1915:
1909:
1868:
1864:
1858:
1833:
1781:
1777:
1739:
1735:
1731:
1727:
1721:
1696:
1692:
1686:
1674:. Retrieved
1621:
1617:
1607:
1564:
1545:February 27,
1543:. Retrieved
1502:
1498:
1488:
1455:
1449:
1443:
1426:. Adelaide:
1423:
1378:
1374:
1364:
1352:. Retrieved
1335:
1279:
1275:
1269:
1261:
1229:(1): 87–95.
1226:
1222:
1216:
1212:
1204:
1171:
1167:
1161:
1149:. Retrieved
1133:
1127:
1115:. Retrieved
1111:the original
1098:
1094:
1084:
1019:
1011:
1004:
951:
948:Biosynthesis
939:
935:
910:carbacephems
830:thiazolidine
816:
810:
806:
802:
798:
794:
790:
786:
782:
778:
758:Nomenclature
749:
741:
734:
720:
716:
708:
684:
626:
613:
603:
599:
592:binding site
579:
571:
569:
543:
531:
507:chloroplasts
503:glaucophytes
460:
429:bactericidal
426:
419:spheroplasts
359:
348:
328:
319:parenterally
316:
297:
278:
253:
234:
210:
205:
199:
187:carbacephems
146:
142:
141:
129:Legal status
67:ring in red.
40:
29:
4046:from market
4025:Teixobactin
4003:Tyrothricin
3972:bactoprenol
3966:Cycloserine
3772:Vaborbactam
3762:Durlobactam
3690:Monobactams
3648:Cefiderocol
3640:Siderophore
3625:Ceftolozane
3539:Cefpimizole
3509:Cefpodoxime
3504:Cefpiramide
3499:Cefmenoxime
3494:Ceftizoxime
3489:Cefdaloxime
3468:Ceftazidime
3457:Ceftriaxone
3429:Carbacephem
3423:Cefmetazole
3379:Cefamandole
3341:Cefatrizine
3321:Cefacetrile
3306:Cefroxadine
3250:Cephamycins
3176:Carbapenems
3132:Mezlocillin
3089:Ticarcillin
3030:Amoxicillin
2996:Methicillin
2971:Cloxacillin
2941:Azidocillin
2931:Propicillin
2876:Penicillins
2680:October 28,
2230:(9): 5229.
1270:Penicillium
1117:November 8,
979:oxidatively
930:monobactams
883:carbapenems
852:oxazolidine
845:carbapenams
841:pyrrolidine
740:-resistant
738:methicillin
695:amoxicillin
680:Amoxicillin
632:β-lactamase
584:carboxylate
366:spirochetal
343:Anaphylaxis
298:Infrequent
293:candidiasis
291:(including
231:Medical use
217:β-lactamase
183:carbapenems
179:monobactams
171:cephamycins
155:beta-lactam
151:antibiotics
135:In Wikidata
57:penicillins
4077:Categories
4013:Tyrocidine
4008:Gramicidin
3976:Bacitracin
3952:Fosfomycin
3923:Ramoplanin
3901:Daptomycin
3767:Relebactam
3740:Tazobactam
3671:Cefquinome
3658:Veterinary
3602:Cefquinome
3592:Cefozopran
3554:Ceftiolene
3544:Cefsulodin
3534:Cefodizime
3519:Cefditoren
3514:Ceftibuten
3462:Cefotaxime
3433:Loracarbef
3399:Cephamycin
3389:Ceforanide
3369:Cefuroxime
3326:Cefalonium
3296:Cefazaflur
3291:Cefazedone
3281:Cefadroxil
3148:Mecillinam
3127:Azlocillin
3103:Temocillin
3044:Hetacillin
3035:Ampicillin
1639:10059/2129
1451:Pediatrics
1336:StatPearls
1223:IMA Fungus
1076:References
1070:Nitrocefin
973:-cysteine-
963:tripeptide
921:oxacephems
805:A cephem.
724:amide bond
703:antagonist
654:transfer (
648:chromosome
564:See also:
534:hydrolases
511:bryophytes
499:organelles
471:amino acid
441:cell walls
333:-mediated
308:angioedema
237:prevention
213:resistance
204:(named as
196:penicillin
159:penicillin
59:(top) and
42:Drug class
4056:Phase III
4044:Withdrawn
4020:Isoniazid
3906:Surfactin
3757:Avibactam
3735:Sulbactam
3708:Carumonam
3703:Tigemonam
3698:Aztreonam
3676:Cefovecin
3666:Ceftiofur
3597:Cefpirome
3568:Latamoxef
3559:Oxacephem
3529:Cefetamet
3484:Cefcapene
3408:Cefotetan
3403:Cefoxitin
3394:Cefuzonam
3384:Cefonicid
3364:Cefprozil
3336:Cefalotin
3311:Ceftezole
3301:Cefradine
3286:Cefapirin
3276:Cefalexin
3271:Cefazolin
3231:Ritipenem
3226:Faropenem
3219:Panipenem
3208:Meropenem
3198:Doripenem
3189:Ertapenem
3070:Epicillin
2991:Nafcillin
2986:Oxacillin
2834:β-lactams
2813:cell wall
2560:S. aureus
2089:0001-4842
2034:1478-7210
1936:0022-2623
1893:0962-8436
1850:1364-5471
1599:210814189
1519:1473-6322
1217:P. rubens
1138:Cited in
1055:Cell wall
823:saturated
793:A penem.
781:A penam.
691:Augmentin
640:hydrolyse
576:angstroms
527:evolution
485:) the Ser
351:urticaria
285:urticaria
191:cell wall
3996:lysozyme
3942:Inhibit
3587:Cefepime
3563:Flomoxef
3549:Cefteram
3524:Cefotiam
3479:Cefdinir
3452:Cefixime
3413:Cefminox
3359:Cefaclor
3224:Penems (
3214:Biapenem
3203:Imipenem
3012:spectrum
3010:Extended
2892:spectrum
2862:-alanine
2858:-alanyl-
2817:envelope
2674:Archived
2670:18163649
2631:16413506
2498:Archived
2494:31205331
2442:23163348
2376:cite web
2360:Archived
2296:cite web
2277:Archived
2256:35563620
2205:36788654
2156:22477821
2107:23902256
2050:68837323
2042:17547502
1993:20065329
1816:22517853
1713:15700950
1670:Archived
1658:27392605
1649:11108400
1591:31939154
1539:Archived
1535:13925217
1527:28742538
1480:21246804
1472:15805383
1405:20930076
1348:Archived
1344:31424895
1314:32973216
1253:22679592
1196:43996071
1188:12679848
1145:Archived
1107:10950216
1050:Bacteria
1029:See also
983:bicyclic
957:(NRPS),
906:pyridine
895:thiazine
868:thiazole
594:and the
588:carbonyl
515:plastids
483:acylates
477:-alanyl-
465:-alanyl-
370:syphilis
335:allergic
304:erythema
223:such as
87:ATC code
65:β-lactam
3242:Cephems
2741:9689037
2709:Bibcode
2596:2708325
2554:of the
2485:6535930
2433:3970115
2412:Bibcode
2247:9100253
2196:9970833
2147:3136230
2098:4018812
1984:2806661
1944:6827544
1901:6109320
1873:Bibcode
1807:3357493
1786:Bibcode
1778:Science
1744:Bibcode
1666:2065821
1396:2952976
1305:7515868
1284:Bibcode
1244:3317369
1151:May 27,
917:oxazine
899:cephems
879:pyrrole
856:clavams
652:plasmid
560:Potency
546:guanine
501:of the
279:Common
175:cephems
122:D047090
4039:WHO-EM
3746:Clavam
3180:Penems
2890:Narrow
2880:Penams
2739:
2729:
2668:
2629:
2594:
2587:209980
2584:
2492:
2482:
2440:
2430:
2335:
2254:
2244:
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