CAS 65277-42-1|1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one|Ketoconazolum [INN-Latin]|Ketozole|Nizoral Cream|nizora...

General Information

Structure

Molecular Formula

C₂₆H₂₈Cl₂N₄O₄

Molecular Mass

531.43092

Exact Mass

530.14876076

Charge

0

InChI

InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

InChIKey

XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Canonic Smiles

Clc1ccc(c(c1)Cl)[C@@]1(OC[C@H](O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1

Isomeric Smiles

Clc1c([C@]2(O[C@@H](CO2)COc2ccc(N3CCN(CC3)C(=O)C)cc2)Cn2ccnc2)ccc(Cl)c1

Calculated Properties

JChem

H Acceptors

6

H Donor

0

LogD (pH = 5.5)

3.6516862

LogD (pH = 7.4)

4.128518

Log P

4.191598

Molar Refractivity

138.0672

Polarizability

53.26531

Polar Surface Area

69.06

Rotatable Bonds

7

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

4.3

LOG S

-4.76

Solubility (Water)

9.31e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

Synonyms

Ketoconazolum [INN-Latin]Ketoconazol [INN-Spanish]KetoconazoleketoconazoleKetocanazole2%Ketoconazole [Usan:Ban:Inn:Jan]Ketoconazol

Brand Name

KetozoleNizoral CreamFungarestNizoral a-D ShampooOrifungalSebazoleKetoisdinNizoralPanfungolNizoral ShampooNizoral a-DFungoralKetodermExtinaOrifungal M

IUPAC Traditional name

nizoral shampoo

Names and Identifiers

Registration numbers

CAS Number

65277-42-1

PubChem CID

47576

PubChem SID

160964362

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

4

Solubility

0.0866 mg/L

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01026

Drug Groups

approved; investigational

Description

Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. [PubChem]

Indication

For the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.

Pharmacology

Ketoconazole, like clotrimazole, fluconazole, itraconazole, and miconazole, is an imidazole antifungal agent.

Toxicity

Hepatotoxicity, LD₅₀=86 mg/kg (orally in rat)

Affected Organisms

Fungi

Biotransformation

Hepatic

Absorption

Moderate

Half Life

2 hours

Protein Binding

99% (in vitro, plasma protein binding)

References

• Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. [Pubmed]

• Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. [Pubmed]

• Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. [Pubmed]

• Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. Pubmed

• Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. Pubmed

• Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. Pubmed

• Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:899