CEFATRIZINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H18N6O5S2
Molecular Weight	462.503
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC3=CN=NN3)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C4=CC=C(O)C=C4)C(O)=O

InChI

InChIKey=UOCJDOLVGGIYIQ-PBFPGSCMSA-N

InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://druginfosys.com/Drug.aspx?drugCode=841&drugName=Cefatrizine&type=1
Curator's Comment: Description was created based on several sources, including https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C81027 and http://www.ncbi.nlm.nih.gov/pubmed/426514

Cefatrizine is a broad-spectrum, semisynthetic, first-generation cephalosporin with antibacterial activity. Cefatrizine binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis. Cefatrizine is used to treat a large variety of bacterial infections, such as respiratory tract, ear, skin and urinary tract infections. Cefatrizine is less effective against gram positive bacteria than first generation drugs. Antibiotics require constant drug level in body for therapeutic effect.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serine/threonine-protein kinase EEF2K 2 Target ID: CHEMBL5026 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26776155	Inhibitor 8297
Bacterial growth 6 Target ID: Bacterial growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/1137381	Inhibitor 8297
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.kegg.jp/dbget-bin/www_bget?D02406	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Bacterial infection of the respiratory tract (bronchitis or bronchopneumonia) 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3044871	Curative	Preclinical	Unknown Approved Use Unknown
Otitis media 41 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3300988	Curative	Preclinical	Unknown Approved Use Unknown
Streptococcal pharyngitis 4 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3099268	Curative	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
European Surveillance of Antimicrobial Consumption (ESAC): outpatient cephalosporin use in Europe.	2006 Aug	16735416
Pharmacokinetics of oral cefatrizine in pregnant and non-pregnant women with reference to fetal distribution.	2007	17135753

Patents

Sample Use Guides

In Vivo Use Guide

It is given by mouth as the base or, more commonly, as a compound with propylene glycol, in usual doses equivalent to 500 mg twice daily of cefatrizine.

Route of Administration: Oral

In Vitro Use Guide

A total of 90% of isolates were inhibited by 1.6 ug of cefatrizine per ml

Name

Type

Language

CEFATRIZINE

Official Name

English

Cefatrizine [WHO-DD]

Common Name

English

CEFATRIZINE [USAN]

Common Name

English

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*)))-

Common Name

English

BL-S640

Code

English

CEFATRIZINE [JAN]

Common Name

English

cefatrizine [INN]

Common Name

English

S-640P

Code

English

CEFATRIZINE PROPYLENE GLYCOLATE [JAN]

Common Name

English

CEFATRIZINE [MI]

Common Name

English

J01DB07

Code

English

(6R,7R)-7-((R)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-8-OXO-3-((V-TRIAZOL-4-YLTHIO)METHYL)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID

Common Name

English

CEFATRIZINE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01DB07