CAS 51627-14-6|Cefatrizine

Introduction：Basic information about CAS 51627-14-6|Cefatrizine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameCefatrizine
CAS Number51627-14-6Molecular Weight462.503
Density1.7±0.1 g/cm3Boiling Point948.1±65.0 °C at 760 mmHg
Molecular FormulaC18H18N6O5S2Melting Point/
MSDS/Flash Point527.2±34.3 °C

Names

NameCefatrizine
SynonymMore Synonyms

Cefatrizine BiologicalActivity

DescriptionCefatrizine (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 CatalogSignaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial
Target

eEF2K, bacterial[1][2].

In VitroCefatrizine (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 VivoCefatrizine (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

Density1.7±0.1 g/cm3
Boiling Point948.1±65.0 °C at 760 mmHg
Molecular FormulaC18H18N6O5S2
Molecular Weight462.503
Flash Point527.2±34.3 °C
Exact Mass462.078003
PSA225.13000
LogP-0.41
Vapour Pressure0.0±0.3 mmHg at 25°C
Index of Refraction1.794
InChIKeyUOCJDOLVGGIYIQ-PBFPGSCMSA-N
SMILESNC(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSc3cn[nH]n3)CSC12)c1ccc(O)cc1

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

Synonyms

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
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