HYDROXYITRACONAZOLE

Details

Stereochemistry	MIXED
Molecular Formula	C35H38Cl2N8O5
Molecular Weight	721.633
Optical Activity	( + / - )
Defined Stereocenters	2 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)C(C)N1N=CN(C1=O)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(OC[C@@H]5CO[C@](CN6C=NC=N6)(O5)C7=C(Cl)C=C(Cl)C=C7)C=C4

InChI

InChIKey=ISJVOEOJQLKSJU-SQWDFJLRSA-N

InChI=1S/C35H38Cl2N8O5/c1-24(25(2)46)45-34(47)44(23-40-45)29-6-4-27(5-7-29)41-13-15-42(16-14-41)28-8-10-30(11-9-28)48-18-31-19-49-35(50-31,20-43-22-38-21-39-43)32-12-3-26(36)17-33(32)37/h3-12,17,21-25,31,46H,13-16,18-20H2,1-2H3/t24?,25?,31-,35-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C35H38Cl2N8O5
Molecular Weight	721.633
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	2 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10702560
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27001813

Hydroxyitraconazole is the antifungally active metabolite of itraconazole formed in the liver by Ω-1-oxidation of itraconazole's 1-methylpropyl substituent. Hydroxyitraconazole has being shown to inhibit ATP-binding cassette yransporters P-Glycoprotein, BCRP, and BSEP..

Approval Year

Targets

Primary Target	Pharmacology	Potency
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27001813	Inhibitor 8297	5.0 µM [IC50]
ATP-binding cassette sub-family G member 2 16 Target ID: CHEMBL5393 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27001813	Inhibitor 8297	12.0 µM [IC50]
Bile salt export pump 15 Target ID: CHEMBL6020 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27001813	Inhibitor 8297	17.0 µM [IC50]
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10702560	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mycoses 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10702560	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antifungal activity of itraconazole compared with hydroxy-itraconazole in vitro.	2000 Mar	10702560

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

In replicate tests with three Candida albicans bioassay strains (NCPF 3241, 3153A and RV 1488) the IC50 value for hydroxyitraconazole was 0.016 mg/L.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:09:15 GMT 2023` Edited by `admin` on `Sat Dec 16 11:09:15 GMT 2023`
Record UNII	0X2BAV045O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDROXYITRACONAZOLE

Common Name

English

Hydroxyitraconazole [WHO-DD]

Common Name

English

R-63373

Code

English

3H-1,2,4-TRIAZOL-3-ONE, 4-(4-(4-(4-(((2R,4S)-2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-1-PIPERAZINYL)PHENYL)-2,4-DIHYDRO-2-(2-HYDROXY-1-METHYLPROPYL)-, REL-

Systematic Name

English

Code System Code Type Description

FDA UNII

0X2BAV045O