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Details

Stereochemistry RACEMIC
Molecular Formula C17H9Cl2FN4O2
Molecular Weight 391.183
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LETRAZURIL

SMILES

FC1=CC=C(C=C1)C(C#N)C2=C(Cl)C=C(C=C2Cl)N3N=CC(=O)NC3=O

InChI

InChIKey=XQKYUBTUOHHNDV-UHFFFAOYSA-N
InChI=1S/C17H9Cl2FN4O2/c18-13-5-11(24-17(26)23-15(25)8-22-24)6-14(19)16(13)12(7-21)9-1-3-10(20)4-2-9/h1-6,8,12H,(H,23,25,26)

HIDE SMILES / InChI

Molecular Formula C17H9Cl2FN4O2
Molecular Weight 391.183
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Letrazuril is the p-fluoro analogue of diclazuril, a benzeneacetonitrile which is active against Eimeria spp., the causative agent of coccidiosis in poultry. Letrazuril is better absorbed and unlike diclazuril produces detectable plasma drug levels in humans following oral administration. In experimental studies on neonatal mice infected with Cryptosporidium parvum, oral administration of letrazuril for 4 days reduced stool oocyst counts by 95-98%, with complete clearing of oocysts from the stool in 47% of animals receiving the higher dose. Letrazuril has the potential to be an effective agent in the treatment of AIDS-related Cryptosporidiosis, without associated major toxicity. Severely immunocompromised AIDS patients with refractory cryptosporidiosis may show a modest, short-lived response to letrazuril. Letrazuril had been in phase I clinical trials for the treatment of cryptosporidiosis. However, this study was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Successful treatment of AIDS-related cryptosporidial sclerosing cholangitis.
1993 Nov
Successful treatment of cryptosporidiosis in an AIDS patient with letrazuril.
1993 Sep
A phase I study of letrazuril in AIDS-related cryptosporidiosis.
1994 Aug
Treatment with letrazuril of refractory cryptosporidial diarrhea complicating AIDS.
1995 Sep 1
Pilot studies of azithromycin, letrazuril and paromomycin in the treatment of cryptosporidiosis.
1997 Feb

Sample Use Guides

50 to 100 mg daily for 6 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:37:38 GMT 2023
Edited
by admin
on Fri Dec 15 18:37:38 GMT 2023
Record UNII
U8736VCB22
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LETRAZURIL
INN   MART.  
INN  
Official Name English
letrazuril [INN]
Common Name English
(±)-(2,6-DICHLORO-4-(4,5-DIHYDRO-3,5-DIOXO-AS-TRIAZIN-2(3H)-YL)PHENYL)(P-FLUOROPHENYL)ACETONITRILE
Common Name English
LETRAZURIL [MART.]
Common Name English
Code System Code Type Description
INN
6445
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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EPA CompTox
DTXSID60869392
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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NCI_THESAURUS
C170113
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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ChEMBL
CHEMBL2104819
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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FDA UNII
U8736VCB22
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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EVMPD
SUB08443MIG
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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SMS_ID
100000082594
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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MESH
C080736
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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PUBCHEM
59745
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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DRUG BANK
DB12663
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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CAS
103337-74-2
Created by admin on Fri Dec 15 18:37:38 GMT 2023 , Edited by admin on Fri Dec 15 18:37:38 GMT 2023
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Related Record Type Details
ACTIVE MOIETY