Cefatrizine

Names

[ Name ]:
Cefatrizine

[Synonym ]:
MFCD00274172
bls640
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-
7-{[Amino(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(2H-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
antibioticbl-640
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(2H-1,2,3-triazol-4-ylthio)methyl]-
7-{[amino(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1H-1,2,3-triazol-5-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefatrizine
7-{[Amino(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
EINECS 257-324-2
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(1H-1,2,3-triazol-5-ylthio)methyl]-
CEPHATHIAMIDINUM
cephatriazine
s640p
Cephathiamidine
antibioticbl-s640

Biological Activity

[Description]:

Cefatrizine (BL-S-640) is an orally active and broad-spectrum cephalosporin antibiotic. Cefatrizine is also a eEF2K inhibitor, with anti-proliferative activity in human breast cancer cells, which could induce ER stress, leading to cell death. Cefatrizine can be used in studies of cancer and bacterial infection[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

eEF2K, bacterial[1][2].

[In Vitro]

Cefatrizine (0-100 µM; 24 h) causes a remarkable anti-proliferative effect on MCF-7 and MDA-MB-436 cell growth in a dose-dependent manner[1]. Cefatrizine (30 µM; 12 h) induces ER stress in breast cancer cells[1]. Cefatrizine (12, 24, 36 h) increases level of CHOP (marker of ER stress induced apoptosis) and promotes expressions of core proteins in eEF2K-modulated ER stress pathways (Bip, p-PERK, XBP-1S and p-JNK) in MCF-7 and MDA-MB-436 cells[1]. Cell Proliferation Assay[1] Cell Line: MCF-7, MDA-MB-436 cells Concentration: 0-100 µM Incubation Time: 24 h Result: Led to a remarkable anti-proliferative effect on cells and resulted in almost 50% inhibition in the MCF-7 and MDA-MB-436 cells when at 33 µM and 29 µM. Cell Viability Assay[1] Cell Line: MCF-7, MDA-MB-436 cells Concentration: 30 µM Incubation Time: 12 h Result: Led to massive cytoplasmic vacuolization.

[In Vivo]

Cefatrizine (BL-S-640) (0.2, 1, 5, 25 mg/kg; p.o.; 4 times daily for 3 days) reduces the number of infecting organisms in the bladder and the kidneys in P. mirabilis intracystically infected model[2]. Animal Model: MaleSwiss-Webster mice (19-21 g; P. mirabilis intracystically infected model)[2]. Dosage: 0.2, 1, 5, 25 mg/kg Administration: Oral administration; 4 times daily for 3 days. Result: Reduced the number of infecting organisms to less than 1,000 in the bladder when 1 mg/kg, and in the kidneys when 0.2 mg/kg.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
948.1±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₁₈N₆O₅S₂

[ Molecular Weight ]:
462.503

[ Flash Point ]:
527.2±34.3 °C

[ Exact Mass ]:
462.078003

[ PSA ]:
225.13000

[ LogP ]:
-0.41

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.794

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XI0340000

CHEMICAL NAME :: 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino(4-hydroxyphenyl)acetyl) amino)-8-oxo-3-((1H-1,2,3-triazol-4-ylthio)methyl)-, (6R-(6-alpha,7-beta(R)))-

CAS REGISTRY NUMBER :: 51627-14-6

LAST UPDATED :: 199410

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C18-H18-N6-O5-S2

MOLECULAR WEIGHT :: 462.54

WISWESSER LINE NOTATION :: T46 ANV ES GUTJ CMVYZR DQ& HVQ G1S- DT5MNNJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >6 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4325 mg/kg

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

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >6 gm/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >240 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >6 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6410 mg/kg

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

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >6 gm/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1600 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1500 mg/kg

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

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >80 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,612,1976 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 175 mg/kg

SEX/DURATION :: female 8-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,129,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2800 mg/kg

SEX/DURATION :: female 8-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,129,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5600 mg/kg

SEX/DURATION :: female 8-14 day(s) after conception

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

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,129,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 175 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,129,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 225 mg/kg

SEX/DURATION :: female 8-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,144,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 8-16 day(s) after conception

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

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 29,144,1976

Related Compounds

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