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3577-01-3

3577-01-3 structure
3577-01-3 structure
  • Name: Cefaloglycin
  • Chemical Name: cefaloglycin
  • CAS Number: 3577-01-3
  • Molecular Formula: C18H19N3O6S
  • Molecular Weight: 405.42500
  • Catalog: API Antibiotics Cephalosporin
  • Create Date: 2018-08-17 10:31:31
  • Modify Date: 2024-01-06 04:19:10
  • Cefaloglycin (Cephaloglycin) is an orally active nephrotoxic β-lactam cephalosporin antibiotic with antibacterial activity. Cefaloglycin is activity against Gram-Positive cocci other than enterococci. Cefaloglycin is toxic to mitochondrial substrate uptake and respiration[1][2][3].
Name cefaloglycin
Synonyms Cefaloglycin
Cephaloglycine
(6R)-3-acetoxymethyl-7t-((R)-2-amino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cephaoglycin acid
(6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefaloglycine
Cefaloglicina
CEPHALOGLYCIN
D-Cephaloglycine
Kafocin
Cefaloglycinum
Cephaloglycin anhydrous
Description Cefaloglycin (Cephaloglycin) is an orally active nephrotoxic β-lactam cephalosporin antibiotic with antibacterial activity. Cefaloglycin is activity against Gram-Positive cocci other than enterococci. Cefaloglycin is toxic to mitochondrial substrate uptake and respiration[1][2][3].
Related Catalog
Target

Gram-Positive cocci[2]

In Vitro Cefaclor to be comparable to Cephaloglycin in terms of in vitro activity against S. pyogenes and somewhat superior to Cephalexin[2].
In Vivo Respiration with and the uptake of succinate and ADP are measured in rabbit renal cortical mitochondria exposed for 2 to 6 h to 300 to 3,000 µg of Cefaloglycin (Cephaloglycin) per mL and then washed to remove the antibiotic. Cefaloglycin (Cephaloglycin) irreversibly reduces both respiration and succinate uptake. The pattern of in vitro injury of Cefaloglycin to mitochondrial substrate uptake and respiration evolves in a time-dependent and concentration-dependent manner[1].
References

[1]. B M Tune, et al. The Renal Mitochondrial Toxicity of Beta-Lactam Antibiotics: In Vitro Effects of Cephaloglycin and Imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21.

[2]. S Shadomy, et al. In Vitro Activities of Five Oral Cephalosporins Against Aerobic Pathogenic Bacteria. Antimicrob Agents Chemother. 1977 Nov;12(5):609-13.

[3]. E Bergogne-Bérézin. Continuous Activity of Significant Antibiotics. Clin Ther. Jan-Feb 1991;13(1):181-8.
Density 1.52 g/cm3
Boiling Point 761.8ºC at 760mmHg
Melting Point 236.5°C (rough estimate)
Molecular Formula C18H19N3O6S
Molecular Weight 405.42500
Flash Point 414.5ºC
Exact Mass 405.09900
PSA 164.33000
LogP 1.01720
Index of Refraction 1.678

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XI0345000
CHEMICAL NAME :
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(2-amino-2-phenylacetamido)- 3-(hydroxymethyl)-8-oxo-, acetate (ester), D-
CAS REGISTRY NUMBER :
3577-01-3
LAST UPDATED :
199603
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C18-H19-N3-O6-S
MOLECULAR WEIGHT :
405.46
WISWESSER LINE NOTATION :
T46 ANV EM GUTJ CMVYZR& G1OV1 HVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Liver - other changes
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1300 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2800 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Liver - other changes
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1030 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3700 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1200 mg/kg
SEX/DURATION :
female 9-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,39,1970
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 gm/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,39,1970
Hazard Codes Xn
Risk Phrases 42/43
Safety Phrases 36
19883-41-1 structure

19883-41-1

957-68-6 structure

957-68-6

~%

3577-01-3 structure

3577-01-3

Literature: Ogasa; Saito; Hashimoto; Sato; Hirata Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 2 p. 315 - 321
7765-60-8 structure

7765-60-8

~%

3577-01-3 structure

3577-01-3

Literature: Spencer; Flynn; Roeske; Siu; Chauvette Journal of medicinal chemistry, 1966 , vol. 9, # 5 p. 746 - 750
33125-05-2 structure

33125-05-2

~%

3577-01-3 structure

3577-01-3

Literature: Spencer; Flynn; Roeske; Siu; Chauvette Journal of medicinal chemistry, 1966 , vol. 9, # 5 p. 746 - 750
24461-61-8 structure

24461-61-8

957-68-6 structure

957-68-6

~%

3577-01-3 structure

3577-01-3

Literature: Kawamori; Hashimoto; Katsumata; et al. Agricultural and Biological Chemistry, 1983 , vol. 47, # 11 p. 2503 - 2509

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title: CAS No. 3577-01-3 | Chemsrc address: https://www.chemsrc.com/en/baike/443453.html

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