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

CC(C)NC(SCC(=O)N[C@H]1[C@H]2SCC(COC(C)=O)=C(N2C1=O)C(O)=O)=NC(C)C

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

Molecular Formula	C19H28N4O6S2
Molecular Weight	472.579
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3104591	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14761333	Curative		Approved 8583	Xianlisu Approved Use Unknown

C_max

Value	Dose	Analyte	Population
9.53 mg/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	7.3 mg/kg single, intravenous dose: 7.3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
46.67 mg/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	29.2 mg/kg single, intravenous dose: 29.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
170.18 mg/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	116.8 mg/kg single, intravenous dose: 116.8 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1004 mg/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	467.6 mg/kg single, intravenous dose: 467.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2.85 mg × h/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	7.3 mg/kg single, intravenous dose: 7.3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
11.31 mg × h/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	29.2 mg/kg single, intravenous dose: 29.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
53.38 mg × h/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	116.8 mg/kg single, intravenous dose: 116.8 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
374.9 mg × h/L EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	467.6 mg/kg single, intravenous dose: 467.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
0.2 h EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	7.3 mg/kg single, intravenous dose: 7.3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.33 h EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	29.2 mg/kg single, intravenous dose: 29.2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.27 h EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	116.8 mg/kg single, intravenous dose: 116.8 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.38 h EXPERIMENT https://www.researchgate.net/publication/285483014_The_pharmacokinetics_study_of_cefathiamidine_in_mice	467.6 mg/kg single, intravenous dose: 467.6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFATHIAMIDINE plasma	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 times / day multiple, intramuscular Studied dose Dose: , 2 times / day Route: intramuscular Route: multiple Dose: , 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/105842/	unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/105842/	Disc. AE: Allergic reaction to drug, Second degree sinoatrial block... AEs leading to discontinuation/dose reduction: Allergic reaction to drug (2 patients) Second degree sinoatrial block (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/105842/

AEs

AE	Significance	Dose	Population
Second degree sinoatrial block	1 pt Disc. AE	2 times / day multiple, intramuscular Studied dose Dose: , 2 times / day Route: intramuscular Route: multiple Dose: , 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/105842/	unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/105842/
Allergic reaction to drug	2 patients Disc. AE	2 times / day multiple, intramuscular Studied dose Dose: , 2 times / day Route: intramuscular Route: multiple Dose: , 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/105842/	unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/105842/

PubMed

Title	Date	PubMed
First four failures of cefathiamidine to treat urogenital gonorrhoea in Guangzhou, China, 2014-15.	2017-06	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)

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:36:55 GMT 2025` Edited by `admin` on `Mon Mar 31 21:36:55 GMT 2025`
Record UNII	8M7CAS5T8L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFATHIAMIDINE

Common Name

English

XIANLISU

Preferred 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

Cefathiamidine [WHO-DD]

Common Name

English

Code System Code Type Description

SMS_ID

100000127416