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Details

Stereochemistry ACHIRAL
Molecular Formula C14H11N3O4
Molecular Weight 285.2548
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIRIMAZOLE

SMILES

OC(=O)C1=CC=C(\C=C\C2=NC=C(N2C=C)[N+]([O-])=O)C=C1

InChI

InChIKey=RBNZISNWCHORNF-VMPITWQZSA-N
InChI=1S/C14H11N3O4/c1-2-16-12(15-9-13(16)17(20)21)8-5-10-3-6-11(7-4-10)14(18)19/h2-9H,1H2,(H,18,19)/b8-5+

HIDE SMILES / InChI
Stirimazole is an imidazole derivative patented by Lilly Industries Ltd. as an antiparasitic agent effective against Trypanosoma congolense, T. gambiense, T. rhodesiense, and T. cruzi. Stirimazole inhibited Trichomonas vaginalis in vitro at 0.225 μg/ml and eliminated infected lesions in mice at 20 mg/kg orally. Stirimazole eliminated intestinal amebiasis in rats at 50 mg/kg orally and hepatic amebiasis in hamsters at 100 mg/kg i.p. Stirimazole was curative against Trypanosoma rhodesiense, Trypanosoma cruzi, Trypanosoma gambiense, and Trypanosoma congolense in mice at 25, 100, 12.5, and 25 mg/kg (4 times, i.p.), respectively, and against Trypanosoma vivax in calves at 25 mg/kg i.v.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antiparasitic nitroimidazoles. 3. Synthesis of 2-(4-carboxystyryl)-5-nitro-1-vinylimidazole and related compounds.
1973 Apr
Patents

Patents

Name Type Language
STIRIMAZOLE
INN  
INN  
Official Name English
stirimazole [INN]
Common Name English
P-(2-(5-NITRO-1-VINYL-2-IMIDAZOLYL)VINYL)BENZOIC ACID
Common Name English
NSC-271231
Code English
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
Code System Code Type Description
NSC
271231
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
INN
3068
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
SMS_ID
100000083502
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104913
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
PUBCHEM
5476886
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
FDA UNII
AX8T791ON0
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
CAS
30529-16-9
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
EVMPD
SUB10653MIG
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID901009868
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY
NCI_THESAURUS
C90759
Created by admin on Fri Dec 15 15:51:06 GMT 2023 , Edited by admin on Fri Dec 15 15:51:06 GMT 2023
PRIMARY