Cefmetazole

Names

[ Name ]:
Cefmetazole

[Synonym ]:
(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
cefmetazolum [INN_la]
(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
Cefmetazole
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-
EINECS 260-384-2
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)-
MFCD00214260

Biological Activity

[Description]:

Cefmetazole (CS 1170) is a semisynthetic cephamycin antibiotic with broad-spectrum antibacterial activity, covering gram-positive, gram-negative and anaerobic bacteria. Cefmetazole binds to penicillin binding proteins (PBPs), resulting in interfering bacterial cell wall biosynthesis. Cefmetazole is used for the research of gynecologic, intraabdominal, urinary tract, respiratory tract and skin and soft tissue infections[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Cefmetazole (CS 1170) has antibiotic affinity to S. aureus with a MIC value of 1.0 mg/L. Cefmetazole has affinity for PBP1, PBP2 and PBP3 with IC50 values of ≤0.3, 0.109 and 0.494 mg/L[1].

[In Vivo]

Cefmetazole (CS 1170) (100 mg/kg; i.h.; twice a day, for 7 days; male ICR mice) alters gut bacterial flora[3]. Animal Model: Male ICR mice[3] Dosage: 100 mg/kg Administration: Subcutaneous injection; twice a day, for 7 days Result: Reduced Peyer's patch (PP) lymphocyte cell numbers while decreased bacterial numbers in the small intestine.

[References]

[1]. Truesdell SE, et, al. Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9.

[2]. Schentag JJ. Cefmetazole sodium: pharmacology, pharmacokinetics, and clinical trials. Pharmacotherapy. 1991;11(1):2-19.

[3]. Yaguchi Y, et, al. Influences of long-term antibiotic administration on Peyer's patch lymphocytes and mucosal immunoglobulin A levels in a mouse model. JPEN J Parenter Enteral Nutr. 2006 Sep-Oct;30(5):395-8; discussion 399.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Melting Point ]:
163-165ºC

[ Molecular Formula ]:
C₁₅H₁₇N₇O₅S₃

[ Molecular Weight ]:
471.534

[ Exact Mass ]:
471.045319

[ PSA ]:
239.23000

[ LogP ]:
0.97

[ Index of Refraction ]:
1.798

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XI0372000

CHEMICAL NAME :: 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)-

CAS REGISTRY NUMBER :: 56796-20-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C15-H17-N7-O5-S3

MOLECULAR WEIGHT :: 471.57

WISWESSER LINE NOTATION :: T46 ANV ES GUTJ CO1 CMV1S1CN HVQ G1S- ET5NNNNJ A1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10233 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair

REFERENCE :: SKKNAJ Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories. (Sankyo K.K. Sogo Kenkyusho, 1-2-58 Hiro-machi, Shinagawa-ku, Tokyo 140, Japan) No.15- 1963- Volume(issue)/page/year: 31,49,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12190 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair

REFERENCE :: SKKNAJ Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories. (Sankyo K.K. Sogo Kenkyusho, 1-2-58 Hiro-machi, Shinagawa-ku, Tokyo 140, Japan) No.15- 1963- Volume(issue)/page/year: 31,49,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8690 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair

REFERENCE :: SKKNAJ Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories. (Sankyo K.K. Sogo Kenkyusho, 1-2-58 Hiro-machi, Shinagawa-ku, Tokyo 140, Japan) No.15- 1963- Volume(issue)/page/year: 31,49,1979 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 9 gm/kg

SEX/DURATION :: female 18-35 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 6,289,1980

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
XI0372200

Synthetic Route

Click to get detail synthetic route

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