CEPHACETRILE

First approved in 1974

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H13N3O6S
Molecular Weight	339.324
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O

InChI

InChIKey=RRYMAQUWDLIUPV-BXKDBHETSA-N

InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C13H13N3O6S
Molecular Weight	339.324
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/768843 | https://www.ncbi.nlm.nih.gov/pubmed/4479816 | https://www.drugbank.ca/drugs/DB01414 | https://www.ncbi.nlm.nih.gov/pubmed/4377 | https://www.ncbi.nlm.nih.gov/pubmed/4211859

Cephacetrile, a parenteral cephalosporin, is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections. It works by inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cephacetrile was used in the treatment of female pelvic inflammatory disease, meningitis and number of other systemic, respiratory and urinary infections.

Originator

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
122.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4479808/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		CEPHACETRILE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
71 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4479808/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		CEPHACETRILE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4479808/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		CEPHACETRILE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-6525	http://www.3bsc.com/index/pro_info.php?id=126884
AA Blocks	AA0085Q0	https://www.aablocks.com/goods/Goods/detail?id=AA0085Q0
Ambinter	Amb17610657	http://www.ambinter.com/reference/17610657
Angene	AGN-PC-0OR70P	http://www.angenechemical.com/productshow/AGN-PC-0OR70P.html
BLD Pharm	BD120237	http://www.bldpharm.com/products/10206-21-0.html
BenchChem	B523054	https://www.benchchem.com/product/b523054
BioSynth	J-000558	https://www.biosynth.com/en/products/all-products/products/J-000558.html
ChemMol	49410184	http://www.chemmol.com/chemmol/49410184.html
Chemspace	CSSB00020619505	https://chem-space.com/CSSB00020619505
DC Chemicals	DC31583	http://www.dcchemicals.com//product_show-Cefacetrile.html
LGC Standards	DRE-A11062500AL-100	https://www.lgcstandards.com/US/en/p/DRE-A11062500AL-100
Lab Network	LN01262273	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01262273
Parchem	47772	https://www.parchem.com/chemical-supplier-distributor/Cefacetrile-------047772.aspx
Smolecule	S523054	http://www.smolecule.com/products/s523054
Smolecule	S774130	https://www.smolecule.com/products/s774130
THE BioTek	bt-263300	https://www.thebiotek.com/product/inhibitors/bt-263300
Yuhao Chemical	XJ3568	http://www.chemyuhao.com/10206-21-0.html
eNovation Chemicals	D674196	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674196

PubMed

Title	Date	PubMed
Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance.	2001 Dec	11814020
[Antimicrobial sensitivity of coagulase-positive staphylococcal strains isolated from bovine mastitis in the central dairy catchment area of Argentina ].	2002 Jul-Sep	12415901

Patents

Sample Use Guides

In Vivo Use Guide

This pharmacokinetic investigation was based on the determination of serum and urinary levles of cephacetrile in 50 subjects given single intramuscular or intravenous doses of 0.5 or 1 gm of the antibiotic; 30 normal subjects, 10 patients with renal insufficiency, and 10 patients with chronic nephritis undergoing maintenance haemodialysis were included in this study.

Route of Administration: Parenteral

In Vitro Use Guide

The MICs were 0.06 to 0.5 ug/ml for Group A Streptococcus, D. pneumoniae, and Staph. aureus, 4-6 ug/ml for E. coli and Klebsiella-Enterobacter 8-32 ug/ml for Pr. mirabilis and more than 500 ug/ml for Ps. aeruginosa. A few strains of Klebsiella and E. coli had MICs of more than 125 ug/ml.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:18:15 UTC 2023` Edited by `admin` on `Fri Dec 15 16:18:15 UTC 2023`
Record UNII	FDM21QQ344
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEPHACETRILE

Common Name

English

CEFACETRILE

Official Name

English

Cefacetrile [WHO-DD]

Common Name

English

VETRIMAST

Brand Name

English

cefacetrile [INN]

Common Name

English

CEPHACETRILE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ51RD34