CEFATHIAMIDINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H28N4O6S2
Molecular Weight	472.579
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC(NC(C)C)=NC(C)C)C(O)=O

InChI

InChIKey=JYXACOFERDBGGQ-RHSMWYFYSA-N

InChI=1S/C19H28N4O6S2/c1-9(2)20-19(21-10(3)4)31-8-13(25)22-14-16(26)23-15(18(27)28)12(6-29-11(5)24)7-30-17(14)23/h9-10,14,17H,6-8H2,1-5H3,(H,20,21)(H,22,25)(H,27,28)/t14-,17-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28384434
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14761333 | https://www.ncbi.nlm.nih.gov/pubmed/3104591 | https://www.ncbi.nlm.nih.gov/pubmed/25499488

Cefathiamidine is a beta-lactam antibiotic that exhibits a broad spectrum of bactericidal activity against gram-positive bacteria. 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. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3104591	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14761333	Curative		Approved 8429	Xianlisu Approved Use Unknown

PubMed

Title	Date	PubMed
First four failures of cefathiamidine to treat urogenital gonorrhoea in Guangzhou, China, 2014-15.	2017 Jun	28384434

Patents

Sample Use Guides

In Vivo Use Guide

1000mg cefathiamidine intramuscularly

Route of Administration: Intramuscular

In Vitro Use Guide

S . faecalis NCTC 775, S . faecium NCTC 7171 and a highly beta-lactam-resistant clinical isolate of S . faecium, strain 37, were used. MICs were determined in Antibiotic Medium 3 (Bacto-penassay broth, Difco) by the broth dilution method. The susceptibility to each of penicillin, ciprofloxacin, spectinomycin and azithromycin was interpreted according to the World Health Organization (WHO) Western Pacific Region Program criteria (Cefathiamidine MIC=2mg/L)

Name

Type

Language

CEFATHIAMIDINE

Common Name

English

LS-150050

Code

English

(7R)-7-(2-((N,N'-DIISOPROPYLAMIDINO)THIO)ACETAMIDO)CEPHALOSPORANIC ACID

Common Name

English

(6R,7R)-7-(2-((N,N'-DIISOPROPYLAMIDINO)THIO)ACETAMIDO)-3-(HYDROXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID ACETATE (ESTER)

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((2-((((1-METHYLETHYL)AMINO)((1-METHYLETHYL)IMINO)METHYL)THIO)ACETYL)AMINO)-8-OXO-, (6R,7R)-

Systematic Name

English

XIANLISU

Brand Name

English

Cefathiamidine [WHO-DD]

Common Name

English

Code System Code Type Description

SMS_ID

100000127416