pramiconazole profile

pramiconazole: has antifungal activity; R-126638 is the (2S-cis)-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	3013050
CHEMBL ID	175633
CHEBI ID	188777
SCHEMBL ID	3048310
MeSH ID	M0509683

Synonyms (30)

Synonym
azoline
r-126638
pramiconazole
1-[4-[4-[4-[[(2s,4r)-4-(2,4-difluorophenyl)-4-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-3-isopropyl-imidazolidin-2-one
r126638
2-imidazolidinone, 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]-1-piperazinyl]phenyl]-3-(1-methylethyl)-
219923-85-0
D06630
pramiconazole (usan/inn)
1-(4-(4-(4-((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)-2-imidazolidinone
r 126638
CHEMBL175633
1-[4-[4-[4-[[(2s,4r)-4-(2,4-difluorophenyl)-4-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-3-propan-2-ylimidazolidin-2-one
CHEBI:188777
1-[4-[4-[4-[[(2s,4r)-4-(2,4-diluorophenyl)-4-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-3-propan-2-ylimidazolidin-2-one
unii-4syh0r661f
2-imidazolidinone, 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)-1-piperazinyl)phenyl)-3-(1-methylethyl)-
4syh0r661f ,
pramiconazole [usan:inn]
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
pramiconazole [inn]
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
pramiconazole [who-dd]
pramiconazole [usan]
SCHEMBL3048310
1-(4-(4-(4-(((2s,4r)-4-((1h-1,2,4-triazol-1-yl)methyl)-4-(2,4-difluorophenyl)-1,3-dioxolan-2-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-3-isopropylimidazolidin-2-one
2-imidazolidinone,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]-1-piperazinyl]phenyl]-3-(1-methylethyl)-
DB06295
DTXSID80944594
AKOS040747301

Research Excerpts

Overview

Pramiconazole (R126638) is a novel azole with potent antifungal activity against yeasts, dermatophytes and many other fungal species. It is a well-tolerated and effective treatment for pityriasis versicolor.

Excerpt	Reference	Relevance
"Pramiconazole (R126638) is a novel azole with potent antifungal activity against yeasts, dermatophytes and many other fungal species. "	( Efficacy of a single oral dose of 200 mg pramiconazole in vulvovaginal yeast infections: an exploratory phase IIa trial. Ausma, J; Borgers, M; Cauwenbergh, G; Donders, G; Janssens, D; Wouters, L, 2008)	2.05
"Pramiconazole is a broad-spectrum triazole antifungal with potential for oral treatment of pityriasis versicolor."	( A double-blind, randomized, placebo-controlled, dose-finding study of oral pramiconazole in the treatment of pityriasis versicolor. Barranco, C; Briones, M; Faergemann, J; Gillies, JD; Pather, S; Quiring, JN; Todd, G; Vawda, ZF; Walford, T, 2009)	2.03
"Pramiconazole is a well-tolerated and effective treatment for pityriasis versicolor and the most effective treatment regimen in this study included 200 or 400 mg taken once, and 200 mg taken once daily for 2 or 3 days."	( A double-blind, randomized, placebo-controlled, dose-finding study of oral pramiconazole in the treatment of pityriasis versicolor. Barranco, C; Briones, M; Faergemann, J; Gillies, JD; Pather, S; Quiring, JN; Todd, G; Vawda, ZF; Walford, T, 2009)	2.03
"Pramiconazole is an antifungal with high potential for the treatment of dermatophyte and yeast infections of the skin. "	( Absence of an active metabolite for the triazole antifungal pramiconazole. Ausma, J; Bohets, H; Borgers, M; Fothergill, A; Pennick, G; van de Velde, V, 2007)	2.02
"Pramiconazole is a novel triazole with potent in vitro antifungal activity, especially against Malassezia spp."	( A pilot study on seborrheic dermatitis using pramiconazole as a potent oral anti-Malassezia agent. Ausma, J; Borgers, M; Cauwenbergh, G; Henry, F; Piérard, GE; Piérard-Franchimont, C; Vroome, V; Wouters, L, 2007)	1.32

Dosage Studied

Excerpt	Relevance	Reference
" It was concluded that there was no active metabolite present in serum samples from healthy volunteers after oral dosing of pramiconazole."	( Absence of an active metabolite for the triazole antifungal pramiconazole. Ausma, J; Bohets, H; Borgers, M; Fothergill, A; Pennick, G; van de Velde, V, 2007)	0.79

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Class	Description
piperazines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (20)

Assay ID	Title	Year	Journal	Article
AID249329	Minimum inhibitory concentration against Candida species (n=24)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249266	Minimum inhibitory concentration against Microsporum species (n=38)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249273	Minimum inhibitory concentration against Trichophyton mentagrophytes (n=20)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID246892	Effective dose was measured in mice infected with Trichophyton mentagrophytes	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249272	Minimum inhibitory concentration against Epidermophyton floccosum (n=12)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249264	Minimum inhibitory concentration against Aspergillus species (n=8)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249344	Minimum inhibitory concentration against Trichophyton mentagrophytes (n=20)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249267	Minimum inhibitory concentration against Trichophyton rubrum (n=14)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249335	Minimum inhibitory concentration against Trichophyton tonsurans (n=18)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249271	Minimum inhibitory concentration against Trichophyton tonsurans (n=18)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249332	Minimum inhibitory concentration against Trichophyton rubrum (n=14)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249269	Minimum inhibitory concentration against Trichophyton species (n=80)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249263	Minimum inhibitory concentration against Candida species (n=24)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID246929	Effective dose was measured in guinea pig infected with Microsporum canis on 14th day	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID246930	Effective dose was measured in guinea pig infected with Microsporum canis on 21st day	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID246926	Effective dose was measured in guinea pig infected with Microsporum canis on 7th day	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249339	Minimum inhibitory concentration against Epidermophyton floccosum (n=12)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249333	Minimum inhibitory concentration against Trichophyton species (n=80)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249330	Minimum inhibitory concentration against Aspergillus species (n=8)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
AID249331	Minimum inhibitory concentration against Microsporum species (n=38)	2005	Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6	Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	12 (85.71)	29.6817
2010's	2 (14.29)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	6 (42.86%)	5.53%
Reviews	1 (7.14%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	7 (50.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.06	1	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
itraconazole [no description available]	2.02	1	0	piperazines
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.43	2	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	2.94	4	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	8.09	14	6	1,2,3-triazole
ergosterol [no description available]	2.02	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.02	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
terbinafine [no description available]	2.44	2	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor

Condition	Relationship Strength	Studies	Trials
Fungal Diseases [description not available]	3.35	2	0
Mycoses Diseases caused by FUNGI.	3.35	2	0
Candidiasis, Genital [description not available]	3.84	2	1
Candidiasis, Vulvovaginal Infection of the VULVA and VAGINA with a fungus of the genus CANDIDA.	3.84	2	1
Malassezia furfur Infection [description not available]	4.39	2	2
Tinea Versicolor A common chronic, noninflammatory and usually symptomless disorder, characterized by the occurrence of multiple macular patches of all sizes and shapes, and varying in pigmentation from fawn-colored to brown. It is seen most frequently in hot, humid, tropical regions and is mostly caused by MALASSEZIA FURFUR (formerly Pityrosporum orbiculare).	4.39	2	2
Dermatitis Any inflammation of the skin.	7.05	1	0
Vaginitis Inflammation of the vagina characterized by pain and a purulent discharge.	7.05	1	0
Bacterial Vaginitides [description not available]	2.06	1	0
Vaginosis, Bacterial Polymicrobial, nonspecific vaginitis associated with positive cultures of Gardnerella vaginalis and other anaerobic organisms and a decrease in lactobacilli. It remains unclear whether the initial pathogenic event is caused by the growth of anaerobes or a primary decrease in lactobacilli.	2.06	1	0
Dermatomycoses Superficial infections of the skin or its appendages by any of various fungi.	3.81	2	1
Dermatophytoses [description not available]	2.02	1	0
Tinea Fungal infection of keratinized tissues such as hair, skin and nails. The main causative fungi include MICROSPORUM; TRICHOPHYTON; and EPIDERMOPHYTON.	2.02	1	0
Dermatitis Seborrheica [description not available]	3.42	1	1
Dermatitis, Seborrheic A chronic inflammatory disease of the skin with unknown etiology. It is characterized by moderate ERYTHEMA, dry, moist, or greasy (SEBACEOUS GLAND) scaling and yellow crusted patches on various areas, especially the scalp, that exfoliate as dandruff. Seborrheic dermatitis is common in children and adolescents with HIV INFECTIONS.	3.42	1	1
Athlete's Foot [description not available]	3.43	1	1
Tinea Pedis Dermatological pruritic lesion in the feet, caused by Trichophyton rubrum, T. mentagrophytes, or Epidermophyton floccosum.	8.43	1	1

pramiconazole

Description

Cross-References

Synonyms (30)

Research Excerpts

Overview

Dosage Studied

Drug Classes (1)

Bioassays (20)

Research

Studies (14)

Market Indicators

Research Demand Index: 25.87

Study Types

pramiconazole

Description

Cross-References

Synonyms (30)

Research Excerpts

Overview

Dosage Studied

Drug Classes (1)

Bioassays (20)

Research

Studies (14)

Market Indicators

Research Demand Index: 25.87

Study Types

Related Drugs (8)

Related Conditions (17)