U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H39F2N7O4
Molecular Weight 659.7255
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAMICONAZOLE

SMILES

CC(C)N1CCN(C1=O)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(OC[C@H]5OC[C@@](CN6C=NC=N6)(O5)C7=C(F)C=C(F)C=C7)C=C4

InChI

InChIKey=AEKNYBWUEYNWMJ-QWOOXDRHSA-N
InChI=1S/C35H39F2N7O4/c1-25(2)43-17-18-44(34(43)45)29-6-4-27(5-7-29)40-13-15-41(16-14-40)28-8-10-30(11-9-28)46-20-33-47-22-35(48-33,21-42-24-38-23-39-42)31-12-3-26(36)19-32(31)37/h3-12,19,23-25,33H,13-18,20-22H2,1-2H3/t33-,35+/m0/s1

HIDE SMILES / InChI
Pramiconazole is a novel azole with potent antifungal activity against yeasts, dermatophytes and many other fungal species. It is a new addition to the family of triazole antifungal agents that act by inhibiting fungal cell membrane ergosterol synthesis, thereby leading to increased cell permeability and destruction. In preclinical studies, pramiconazole exhibited similar or superior antifungal activity to ketoconazole and itraconazole, and selectively inhibited ergosterol synthesis with a broad spectrum activity. Pramiconazole was absorbed rapidly and had a long half-life, allowing for once-daily dosing. In phase I and II clinical trials, pramiconazole reduced the growth of Candida albicans, Malassezia globosa, Microsporum canis, Trichophyton mentagrophytes and Trichophyton rubrum, and was generally well tolerated. Pramiconazole is a well-tolerated and effective treatment for pityriasis versicolor.

Approval Year

PubMed

PubMed

TitleDatePubMed
The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis.
2004 Sep
Gateways to clinical trials.
2006 Oct
Absence of an active metabolite for the triazole antifungal pramiconazole.
2007
The efficacy of oral treatment with pramiconazole in pityriasis versicolor: a phase II a trial.
2007 Jun
Efficacy of a single oral dose of 200 mg pramiconazole in vulvovaginal yeast infections: an exploratory phase IIa trial.
2008
The efficacy of oral treatment with pramiconazole in tinea pedis and tinea cruris/corporis: two exploratory phase IIa trials.
2008 Apr
Gateways to clinical trials.
2008 May
Pramiconazole, a triazole compound for the treatment of fungal infections.
2008 Sep
A double-blind, randomized, placebo-controlled, dose-finding study of oral pramiconazole in the treatment of pityriasis versicolor.
2009 Dec

Sample Use Guides

200 or 400 mg taken once, and 200 mg taken once daily for 2 or 3 days
Route of Administration: Oral
Name Type Language
PRAMICONAZOLE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
Pramiconazole [WHO-DD]
Common Name English
pramiconazole [INN]
Common Name English
1-[4-[4-[4-[[(2S,4R)-4-(2,4-Difluorophenyl)-4-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-3-(1-methylethyl)imidazolidin-2-one
Systematic Name English
R-126638
Code English
R126638
Code English
PRAMICONAZOLE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
Code System Code Type Description
SMS_ID
300000034320
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
PUBCHEM
3013050
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
CAS
219923-85-0
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID80944594
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
MESH
C482452
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
INN
8769
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
DRUG BANK
DB06295
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
NCI_THESAURUS
C72830
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL175797
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
FDA UNII
4SYH0R661F
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
WIKIPEDIA
PRAMICONAZOLE
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY
USAN
RR-98
Created by admin on Fri Dec 15 16:28:52 GMT 2023 , Edited by admin on Fri Dec 15 16:28:52 GMT 2023
PRIMARY