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56796-20-4

56796-20-4 structure
56796-20-4 structure
  • Name: Cefmetazole
  • Chemical Name: cefmetazole
  • CAS Number: 56796-20-4
  • Molecular Formula: C15H17N7O5S3
  • Molecular Weight: 471.534
  • Catalog: API Antibiotics Cephalosporin
  • Create Date: 2018-07-20 19:19:54
  • Modify Date: 2024-01-02 12:07:49
  • 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].
Name cefmetazole
Synonyms (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
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
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.
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

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
Hazard Codes Xn
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS XI0372200

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