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Thienamycins

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Definition: Beta-lactam antibiotics that differ from PENICILLINS in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. They are unstable chemically, but have a very broad antibacterial spectrum. Thienamycin and its more stable derivatives are proposed for use in combinations with enzyme inhibitors.     
Pharmacological Action Anti-Bacterial Agents
Examples Imipenem
Other names Antibiotics, Thienamycin; Thienamycin Antibiotics
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
BO 2502A  0   *Thienamycins. J Antibiot (Tokyo) 1997 Jul;50(7):567-85
desmethyl meropenem  0   *Thienamycins. Biiorg Med Chem 1998 Apr;6(4):367-75
FR 27743  0   *Thienamycins. Bioorg Med Chem 1997 Nov;5(11):2069-87
2-methylthiocarbapenem  118243-53-1   *Thienamycins. J Antibiot (Tokyo) 1993 May;46(5):827-32
panipenem-betamipron  138240-65-0   Thienamycins beta-Alanine/analogs & derivatives.
Pharma Action Anti-Bacterial Agents
Jpn J Antibiot 1992 Feb;45(2):143-54
6-(2'-hydroxyethylidene)-4-methyl-3-(2-(methylthio)pyridinyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate  140631-65-8   *Thienamycins. J Antibiot (Tokyo) 1992 Feb;45(2):240-5
biapenem  120410-24-4 5H-Pyrazolo(1,2-a)(1,2,4)triazol-4-ium, 6-((2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-, hydroxide, inner salt, (4R-(4alpha,5beta,6beta(R*)))  *Thienamycins.
Pharma Action Anti-Infective Agents
Antimicrob Agents Chemother 1990;34(6):994
antibiotic 88617  112525-65-2 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(dimethylamino)-2-(methylimino)ethyl)thio)-6-(1-fluoroethyl)-7-oxo-, (5R-(5alpha,6alpha(R*)))  *Thienamycins. J Antibiot (Tokyo) 1989;42(10):1520
meropenem  96036-03-2 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((5-((dimethylamino)carbonyl)-3-pyrrolidinyl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4R-(3(3S*,5S*),4alpha,5beta,6beta(R*)))  *Thienamycins.
Pharma Action Anti-Bacterial Agents
Antimicrob Agents Chemother 1989;33(2):215MERREM; MEROPENEM
6-(1-hydroxyethyl)-2-(1-acetimidoylpyrrolidin-3-ylthio)-1-methyl-1-carbapen-2-em-3-carboxylic acid  103730-44-5   *Thienamycins. J Antibiot (Tokyo) 1989;42(3):374
epithienamycin E  79057-46-8   *Thienamycins. J Antibiot (Tokyo) 1988;41(5):707
OA 6129E  85414-26-2 1-Azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-((2-((3-((2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)amino)-1-oxopropyl)amino)ethyl)thio)-6-(1-hydroxy-1-methylethyl)-7-oxo-, (2S-(2alpha,3alpha(S*),5alpha,6beta))  *Thienamycins. J Antibiot (Tokyo) 1984;37(3):211
OA 6129D  85414-25-1 1-Azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-((2-((3-((2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)amino)-1-oxopropyl)amino)ethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (2S-(2alpha,3alpha(S*),5alpha,6beta(R*)))  *Thienamycins. J Antibiot (Tokyo) 1984;37(3):211
17927 D  74660-91-6   *Thienamycins. J Antibiot (Tokyo) 1983;36(11):1581
northienamycin  77550-86-8   *Thienamycins. J Antibiot (Tokyo);36(9):1109
panipenem  87726-17-8 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-3-((1-(1-iminoethyl)-3-pyrrolidinyl)thio)-7-oxo-, (5R-(3(S*),5alpha,6alpha(R*)))  *Thienamycins. J Antibiot (Tokyo) 1983;36(8):1034
carpetimycin D  87139-37-5   *Thienamycins. J Antibiot (Tokyo) 1983;36(8):943
carpetimycin C  87695-64-5   *Thienamycins. J Antibiot (Tokyo) 1983;36(8):943
OA 6129C  82475-09-0 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-((3-((2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)amino)-1-oxopropyl)amino)ethyl)thio)-7-oxo-6-(1-(sulfooxy)ethyl)  *Thienamycins. J Antibiot (Tokyo) 1982;35(10):1255
OA 6129B(1)  82510-13-2 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-((3-((2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)amino)-1-oxopropyl)amino)ethyl)thio)-6-(1-hydroxyethyl)-7-oxo  *Thienamycins. J Antibiot (Tokyo) 1982;35(10):1255
OA 6129A  82475-11-4 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-((3-((2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)amino)-1-oxopropyl)amino)ethyl)thio)-6-ethyl-7-oxo-, (5R-(3(R*),5alpha,6alpha))  *Thienamycins. J Antibiot (Tokyo) 1982;35(10):1255
antibiotic 6643-X  82889-90-5 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethyl)thio)-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (R-(E))  *Thienamycins. J Antibiot (Tokyo) 1982;35(9):1237
antibiotic C 19393E5  83310-72-9 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)sulfinyl)-6-(1-hydroxyethyl)-7-oxo-, (5R-(3(R*(E)),5alpha,6beta(S*)))  *Thienamycins. J Antibiot (Tokyo) 1982;35(8):957
Sch 33755  72888-55-2 4-Thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (5R-(5alpha,6alpha(R*)))  *Thienamycins. Chem Pharm Bull (Tokyo) 1981;29(11):3158
asparenomycin  76466-24-5 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)sulfinyl)-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (R-(R*,R*-(E,E)))  *Thienamycins. J Antibiot (Tokyo) 1981;34(7):909
8-dehydroxythienamycin  74806-75-0 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-ethyl-7-oxo-, (5R-cis)  *Thienamycins. J Antibiot (Tokyo) 1981;34(3):341
carpetimycin B  76094-36-5 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)sulfinyl)-6-(1-methyl-1-(sulfooxy)ethyl)-7-oxo-, (5R-(3(R*(E)),5alpha,6beta))  *Thienamycins. J Antibiot (Tokyo) 1980;33(11):1388
carpetimycin A  76025-73-5 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)sulfinyl)-6-(1-hydroxy-1-methylethyl)-7-oxo-, (5R-(3(R*(E)),5alpha,6beta))  *Thienamycins. J Antibiot (Tokyo) 1980;33(11):1388
delta(1)-thienamycin  77171-32-5 1-Azabicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (2S-(2alpha,5alpha,6alpha(S*)))  *Thienamycins. J Med Chem 1981;24(5):639
antibiotic PS 7  72615-18-0 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)thio)-6-ethyl-7-oxo-, (5R-(3(E),5alpha,6alpha))  *Thienamycins. J Antibiot (Tokyo) 1980;33(10):1128
antibiotic PS 6  72615-19-1 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethyl)thio)-6-(1-methylethyl)-7-oxo-, (5R-cis)  *Thienamycins. J Antibiot (Tokyo) 1980;33(10):1128
PS 5  67007-79-8 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethyl)thio)-6-ethyl-7-oxo-, monosodium salt  *Thienamycins. J Antibiot (Tokyo) 1980;33(8):796; J Antibiot (Tokyo) 32(4):262;1979; J Antibiot (Tokyo) 32(4):272;1979; J Antibiot (Tokyo) 32(4):280;1979; J Antibiotics 31(5):480;1978
thienamycin  64090-99-9 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-,  *Thienamycins.
Pharma Action Anti-Bacterial Agents
Antibiotiki 25(1):60;1980; Antimicrob Agents Chemother 12(3):406;1977; Antimicrob Agents Chemother 14(3):436;1978; Antimicrob Agents Chemother 15(4):518;1979; Antimicrob Agents Chemother 15(6):831;1979; Eur J Biochem 91(2):509;1978; J Antibiot (Tokyo) 32(1):1;1979; J Med Chem 1979;22(12):1435; Scand J Infect Dis (Suppl)13:11;1978

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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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