Cefmetazole acid

Semisynthetic cephamycin β-lactam antibiotic used for the treatment of susceptible bacterial infections. Cefmetazole inhibits bacterial cell-wall synthesis by binding to penicillin-binding proteins and interfering with peptidoglycan cross-linking. It has activity against a range of Gram-positive and Gram-negative bacteria

CAS Number: 56796-20-4

Molecular Mass: 471.5 g/mol

Formula: C₁₅H₁₇N₇O₅S₃

Smiles: CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21

Synonymes:

Cefmetazole acid, cefmetazole, 56796-20-4, Cefmetazolo, Cefmetazolum, (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Cefmetazol, 3J962UJT8H, CHEBI:3489, U-72791, DTXSID7022756, (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-cis)-, (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-7-((((cyanomethyl)sulfanyl)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)sulfanyl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7S)-7-((2-(cyanomethylsulfanyl)acetyl)amino)-7-methoxy-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7S)-7-(2-((cyanomethyl)sulfanyl)acetamido)-7-methoxy-3-(((1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, RefChem:574974, DTXCID502756, J01DA40, 260-384-2, CS1170, Cefmetazolum [INN-Latin], Cefmetazolo [INN-Spanish], MFCD00865068, 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-, (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, SKF 83088, CS 1170, C15H17N7O5S3, U 72791, Cefmetazole (USP/INN), EINECS 260-384-2, BRN 0634647, UNII-3J962UJT8H, Cefmetazole [USAN:USP:INN], (6R,7S)-7-[2-[(Cyanomethyl)thio]acetamido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 56796-20-4 (free), CefmetaZole, 95%, CEFMETAZOLE [MI], Prestwick0_000700, Prestwick1_000700, Prestwick2_000700, Prestwick3_000700, CEFMETAZOLE [INN], CEFMETAZOLE [USAN], Epitope ID:116204, CEFMETAZOLE [VANDF], CEFMETAZOLE [MART.], CS 1170, SKF 83088, U 72791, U 72791a, Lopac0_000266, BSPBio_000859, CEFMETAZOLE [USP-RS], CEFMETAZOLE [WHO-DD], SCHEMBL147832, SPBio_002780, BPBio1_000945, orb1710132, CEFMETAZOLE SODIUM [JAN], CHEMBL1201195, GTPL12215, MSK2846, SNBUBQHDYVFSQF-HIFRSBDPSA-N, CEFMETAZOLE [USP IMPURITY], CEFMETAZOLE [USP MONOGRAPH], HY-B1595, BDBM50350471, EBC-27178, T1070L, AKOS015896219, DB00274, SDCCGSBI-0050254.P002, (6R,7S)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, sodium salt, AC-13154, BS-42476, CS-0013513, NS00011557, C08103, D00910, EN300-19766367, -1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Q5057238, BRD-K48470486-236-10-8, (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia, (6R,7S)-7-{2-[(Cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7beta-{[(cyanomethyl)sulfanyl]acetamido}-7alpha-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid

Bioactivity: β-Lactam antibiotic; bacterial cell-wall synthesis inhibitor; second-generation cephalosporin/cephamycin

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
Ethanol	278.15	-	1.767	[30]
Ethanol	278.15	-	2.185	[31]
Ethanol	283.15	-	2.299	[30]
Ethanol	283.15	-	2.251	[31]
Ethanol	288.15	-	3.001	[30]
Ethanol	288.15	-	2.786	[31]
Ethanol	293.15	-	3.775	[30]
Ethanol	293.15	-	3.517	[31]
Ethanol	298.15	-	4.797	[30]
Ethanol	298.15	-	3.939	[31]
Ethanol	303.15	-	6.051	[30]
Ethanol	303.15	-	5.271	[31]
Isopropanol	278.15	-	0.288	[30]
Isopropanol	283.15	-	0.3837	[30]
Isopropanol	288.15	-	0.5076	[30]
Isopropanol	293.15	-	0.6565	[30]
Isopropanol	298.15	-	0.8452	[30]
Isopropanol	303.15	-	1.061	[30]
Methanol	278.15	-	18.3	[30]
Methanol	278.15	-	19.37	[31]
Methanol	283.15	-	23.9	[30]
Methanol	283.15	-	22.12	[31]
Methanol	288.15	-	30.96	[30]
Methanol	288.15	-	26.03	[31]
Methanol	293.15	-	39.38	[30]
Methanol	293.15	-	31.9	[31]
Methanol	298.15	-	49.89	[30]
Methanol	298.15	-	42.23	[31]
Methanol	303.15	-	63.06	[30]
Methanol	303.15	-	51.47	[31]
Water	278.15	-	0.4101	[30]
Water	283.15	-	0.5353	[30]
Water	288.15	-	0.693	[30]
Water	293.15	-	0.9045	[30]
Water	298.15	-	1.145	[30]
Water	303.15	-	1.438	[30]

Molecule 3D descriptors

Descriptor	Value
PMI1	3215.3758
PMI2	6070.6823
PMI3	8070.0544
NPR1	0.3984
NPR2	0.7522
RadiusOfGyration	4.2899
InertialShapeFactor	0.0002
Eccentricity	0.9172
Asphericity	0.2371
SpherocityIndex	0.2087
PBF	1.0159