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Details

Stereochemistry EPIMERIC
Molecular Formula C18H18N6O5S2.C3H8O2
Molecular Weight 538.597
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFATRIZINE PROPYLENE GLYCOLATE

SMILES

CC(O)CO.[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=CKOIKOHDEYTLFR-PFBPGKLMSA-N
InChI=1S/C18H18N6O5S2.C3H8O2/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;1-3(5)2-4/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23);3-5H,2H2,1H3/t12-,13-,17-;/m1./s1

HIDE SMILES / InChI
Molecular Formula C18H18N6O5S2
Molecular Weight 462.503
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C3H8O2
Molecular Weight 76.0944
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Preclinical
Unknown

Approved Use

Unknown
Curative
Preclinical
Unknown

Approved Use

Unknown
Curative
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
Pathogen incidence and antibiotic resistance patterns of catheter-associated urinary tract infection in children.
2009 Dec
Antibiotic Treatment of Dogs and Cats during Pregnancy.
2010 Dec 14
Patents

Patents

20010044416
23

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be administered i.v. http://www.ncbi.nlm.nih.gov/pubmed/6660858
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
Curator's Comment: Bacterial isolates were from urine, sputum, throat, stool, and wound cultures of patients. Cefatrizine inhibited the majority of Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, and Salmonella at concentrations below 12.5 mug/ml.
A total of 90% of isolates were inhibited by 1.6 ug of cefatrizine per ml
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:57:12 GMT 2023
Edited
by admin
on Fri Dec 15 18:57:12 GMT 2023
Record UNII
3731IA5GI9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFATRIZINE PROPYLENE GLYCOLATE
Common Name English
CEFATRIZINE COMPD WITH PROPYLENE GLYCOL [MI]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETYL)AMINO)-8-OXO-3-((1H-1,2,3-TRIAZOL-5-YLTHIO)METHYL)-, (6R,7R)-, COMPD. WITH 1,2-PROPANEDIOL (1:1)
Common Name English
CEFATRIZINE PROPYLENE GLYCOL [EP IMPURITY]
Common Name English
OROTRIC
Brand Name English
CEFATRIZINE PROPYLENEGLYCOLATE
WHO-DD  
Common Name English
SEAPURO
Brand Name English
CEFATRIZINE PROPYLENE GLYCOL [EP MONOGRAPH]
Common Name English
CEFATRIZINE PROPYLENE GLYCOL
EP   MART.  
Common Name English
CEFATRIZINE COMPD WITH PROPYLENE GLYCOL
MI  
Common Name English
CEFATRIZINE PROPYLENE GLYCOL [MART.]
Common Name English
Cefatrizine propyleneglycolate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID00972733
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
CAS
57235-40-2
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
NON-SPECIFIC STOICHIOMETRY
SMS_ID
100000091867
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
EVMPD
SUB11797MIG
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
CAS
64217-62-5
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
PUBCHEM
6410757
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
FDA UNII
3731IA5GI9
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
MERCK INDEX
m3187
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C98215
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
260-642-4
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL286398
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
DRUG BANK
DBSALT002708
Created by admin on Fri Dec 15 18:57:13 GMT 2023 , Edited by admin on Fri Dec 15 18:57:13 GMT 2023
PRIMARY
Related Record Type Details
Structure of CEFATRIZINE
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of 7-TACA
IMPURITY -> PARENT
Related Record Type Details
Structure of CEFATRIZINE
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