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Carbapenems

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Definition: A group of beta-lactam antibiotics in which the sulfur atom in the thiazolidine ring of the penicillin molecule is replaced by a carbon atom. THIENAMYCINS are a subgroup of carbapenems which have a sulfur atom as the first constituent of the side chain.     
Examples Thienamycins 		Other names Antibiotics, Carbapenem; Carbapenem Antibiotics
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
1-ethylpropyloxycarbonyloxymethyl (1R,5S,6S)-2-((3S,5S)-5-(N,N-dimethylcarbamoyl)-1-(isobutyryloxymethyloxycarbonyl)pyrrolidin-3-ylthio)-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate  0   *Carbapenems. J Antibiot (Tokyo). 2011 Mar;64(3):233-42
pivaloyloxymethyl(1R,5S,6S)-2-((3S,5S)-5-(N,N-dimethylcarbamoyl)-1-(isobutyryloxymethyloxycarbonyl)pyrrolidin-3-ylthio)-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate  0   *Pyrrolidines *Carbapenems. J Antibiot (Tokyo). 2011 Mar;64(3):233-42
LK-157  0   *Carbapenems. Antimicrob Agents Chemother 2009 Feb;53(2):505-11
CP5484  0   *Carbapenems. Bioorg Med Chem 2007 Oct 1;15(19):6379-87
CW-270033  0   *Pyrrolidines *Carbapenems. Biol Pharm Bull 2007 Mar;30(3):575-9
OCA-983  0   *Carbapenems. Med Chem 2006 Jan;2(1):21-5
tebipenem  0   *Carbapenems. Antimicrob Agents Chemother 2005 Mar;49(3):889-94
SM-216601  0   *Carbapenems. J Antibiot (Tokyo). 2005 Feb;58(2):118-40
R 115685  0   *Carbapenems. J Antimicrob Chemother 2004 Aug;54(2):557-62
ME1036  0   *Carbapenems. Antimicrob Agents Chemother. 2004 Aug;48(8):2831-7
CP0569  0   *Carbapenems. Bioorg Med Chem. 2003 Aug 5;11(16):3475-85
1 beta-methylcarbapenem  0   *Carbapenems. Bioorg Med Chem Lett. 2003 Feb 10;13(3):463-6
6-(1-hydroxyethyl)-3-((4-(2-(hydroxymethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1,3-thiazol-2-yl)thio)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid  0   *Carbapenems. J Antibiot (Tokyo) 2002 Aug;55(8):722-57
6-(1-hydroxyethyl)-4-methyl-3-((4-(2-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1,3-thiazol-2-yl)thio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid  0   *Carbapenems. J Antibiot (Tokyo) 2002 Aug;55(8):722-57
3-((4-(2,5-dihydro-1H-pyrrol-3-yl)-1,3-thiazol-2-yl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid  0   *Carbapenems. J Antibiot (Tokyo) 2002 Aug;55(8):722-57
1-aza-6-(1-hydroxyethyl)-4-methyl-7-oxo-3-(((2-(1,2,3-thiadiazol-5-yl)thiomethyl)pyrrolidin-4-yl)thio)bicyclo(3.2.0)heptane-2-carboxylic acid  0   *Carbapenems. Bioorg Med Chem Lett 2001 Sep 3;11(17):2397-9
TA 949  0   Carbapenems. J Org Chem 2000 Jan 28;65(2):517-22
KR 21012  0   *Carbapenems. Bioorg Med Chem Lett 2000 Feb 21;10(4):333-6
J 114870  0   *Carbapenems Stereoisomerism. Bioorg Med Chem Lett 2000 Jan 17;10(2):115-8
J 111225  0   *Carbapenems. Bioorg Med Chem Lett 2000 Jan 17;10(2):115-8
J 111347  0   *Carbapenems. Bioorg Med Chem Lett 2000 Jan 17;10(2):109-13
DK 35C  0   *Carbapenems. Toxicology 1999 Nov 5;138(2):59-67
L 084  0   *Carbapenems. Antimicrob Agents Chemother 1999 Aug;43(8):2010-6
LJC 11036  0   *Carbapenems. Antimicrob Agents Chemother 1999 Aug;43(8):2010-6
CL 191121  0   *Carbapenems. Antimicrob Agents Chemother 1999 Mar;43(3):454-9
MK 826  0   *Carbapenems. J Pharm Sci 1999 Feb;88(2):277-80
L 786392  0   *Lactams *Thiazoles Carbapenems. Science 1999 Jan 29;283(5402):703-6
PGE-5428060  0   *Carbapenems. J Antibiot (Tokyo) 1998 Sep;51(9):857-71
R 95867  0   *Carbapenems. Antimicrob Agents Chemother 1997 Dec;41(12):2652-63
BO 3482  0   *Carbapenems. Antimicrob Agents Chemother 1997 Oct;41(10):2278-81
L 749345  0   *Carbapenems. Antimicrob Agents Chemother 1997 Aug;41(8):1743-8
CS 834  0   *Carbapenems. J Antibiot (Tokyo) 1997 May;50(5):429-39
DZ 2640  0   *Carbapenems. Antimicrob Agents Chemother 1997 Jun;41(6):1260-8
DU 6681  0   *Carbapenems. Antimicrob Agents Chemother 1997 Jun;41(6):1260-8
beta-methyl ADC-13 enolphosphate diphenyl ester  0   *Phosphoric Acid Esters *Carbapenems. J Chromatogr A 1997 Feb 21;762(1-2):327-33
ER 35786  0   *Pyrrolidines *Carbapenems. Antimicrob Agents Chemother 1997 Feb;41(2):298-307
doripenem  0   *Carbapenems. J Antibiot (Tokyo) 1996 Feb;49(2):199-209DORIBAX
DA 1131  0   *Carbapenems. Res Commun Mol Pathol Pharmacol 1995 Dec;90(3):347-62
DX 8739  0   *Carbapenems. Antimicrob Agents Chemother 1995 Mar;39(3):731-4
SM 17466  0   *Carbapenems. Antimicrob Agents Chemother 1995 Apr;39(4):910-6
1-carbapen-2-em-3-carboxylic acid  110453-77-5   *Carbapenems. Biochem Soc Trans 1995 Feb;23(1):127S
L 695256  0   Imidazoles Carbapenems. Antimicrob Agents Chemother 1995 Feb;39(2):462-6
BMS 181139  0   *Guanidines *Carbapenems. Antimicrob Agents Chemother 1995 Feb;39(2):380-5
BO 2727  149882-71-3 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-3-((5-(1-hydroxy-3-(methylamino)propyl)-3-pyrrolidinyl)thio)-4-methyl-7-oxo-, monohydrochloride, (4R-(3(3S*,5S*(R*)),4alpha,5beta,6beta(R*)))  *Carbapenems. Antimicrob Agents Chemother 1993 Dec;37(12):2756-9
2-hydroxymethyl-1-carbapenam  139748-18-8   *Carbapenems. Chem Pharm Bull (Tokyo) 1991 Nov;39(11):2813-8
FCE 25199  140881-20-5   *Carbapenems. APMIS 1991;99(10):916
SUN 5555  122547-49-3 4-Thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, monosodium salt, (5R-(3(R*),5alpha,6alpha(R*)))  *Carbapenems. J Antibiot (Tokyo) 1989;42(6):977
6-(1-hydroxyethyl)-2-(5-chloro-2-oxobenzoxazolin-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylic acid  125412-71-7   *Carbapenems. J Antibiot (Tokyo) 1989;42(3):374
ritipenem  84845-57-8   *Carbapenems. Antimicrob Agents Chemother 1983;24(6):909
carbapenem-3-carboxylic acid  82768-37-4 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 7-oxo  *Carbapenems. J Antibiot (Tokyo) 1982;35(6):653
pluracidomycin  82138-64-5 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 7-oxo-3-sulfo-6-(1-(sulfooxy)ethyl)-, (5R-(5alpha,6beta(S*)))  *Carbapenems beta-Lactamases/antagonists & inhibitors. J Antibiot (Tokyo) 1982;35(4):533; J Antibiot (Tokyo) 1982;35(4):536

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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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