KETOCONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H28Cl2N4O4
Molecular Weight	531.431
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N1CCN(CC1)C2=CC=C(OC[C@@H]3CO[C@](CN4C=CN=C4)(O3)C5=CC=C(Cl)C=C5Cl)C=C2

InChI

InChIKey=XMAYWYJOQHXEEK-ZEQKJWHPSA-N

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

HIDE SMILES / InChI

Molecular Formula	C26H28Cl2N4O4
Molecular Weight	531.431
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27600150https://www.ncbi.nlm.nih.gov/pubmed/25775613 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf | https://www.drugbank.ca/drugs/DB01026
Curator's Comment: Description was created based on several sources, including http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2016.NP.15.SAT-547 | https://www.ncbi.nlm.nih.gov/pubmed/18640464 | https://www.ncbi.nlm.nih.gov/pubmed/25000292

Ketoconazole is an azole antifungal. Ketoconazole was the first broad-spectrum oral antifungal agent available to treat systemic and superficial mycoses. Evidence of hepatotoxicity associated with its use emerged within the first few years of its approval. Due to its hepatotoxic side effects, oral ketoconazole was withdrawn from the European and Australian markets in 2013. The United States imposed strict relabeling requirements and restrictions for prescription, with Canada issuing a risk communication echoing these concerns. Today, oral ketoconazole is only indicated for endemic mycoses, where alternatives are not available or feasible. Meanwhile, topical ketoconazole is effective, safe, and widely prescribed for superficial mycoses, particularly as the first-line treatment for tinea versicolor. Topically administered ketoconazole is usually prescribed for fungal infections of the skin and mucous membranes, such as athlete's foot, ringworm, candidiasis (yeast infection or thrush), jock itch, and tinea versicolor. Topical ketoconazole is also used as a treatment for dandruff (seborrheic dermatitis of the scalp) and for seborrheic dermatitis on other areas of the body, perhaps acting in these conditions by suppressing levels of the fungus Malassezia furfur on the skin. Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone. Ketoconazole is active against clinical infections with Blastomyces dermatitidis, Coccidioides immitis, Histoplasma capsulatum, Paracoccidioides brasiliensis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Aryl hydrocarbon receptor 27 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25000292	Agonist 2752	2.2 µM [EC50]
Aryl hydrocarbon receptor 27 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25000292	Antagonist 2849	17.5 µM [IC50]
Cytochrome P450 11B1 9 Target ID: CHEMBL1908 Sources: http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2016.NP.15.SAT-547	Inhibitor 8504	116.0 nM [IC50]
Cytochrome P450 17A1 8 Target ID: CHEMBL3522 Sources: http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2016.NP.15.SAT-547	Inhibitor 8504	48.0 nM [IC50]
Cytochrome P450 21 4 Target ID: CHEMBL2759 Sources: http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2016.NP.15.SAT-547	Inhibitor 8504	1.0 µM [IC50]
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: https://www.drugbank.ca/drugs/DB01026 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/018533s040lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/23826084	Inhibitor 8504	27.0 nM [Kd]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26614990	Inhibitor 8504	0.18 µM [IC50]
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1526623	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Tinea corporis 19 Sources: https://www.drugs.com/cdi/ketoconazole-cream.html	Curative	Approved 8583	NIZORAL Approved Use Ketoconazole Cream, 2% is indicated for the topical treatment of tinea corporis, tinea cruris and tinea pedis caused by Trichophyton rubrum, T. mentagrophytes and Epidermophyton floccosum; in the treatment of tinea (pityriasis) versicolor caused by Malassezia furfur (Pityrosporum orbiculare); in the treatment of cutaneous candidiasis caused by Candida spp. and in the treatment of seborrheic dermatitis. Launch Date 1981
Tinea pedis 28 Sources: https://www.drugs.com/pro/ketoconazole-cream.html	Curative	Approved 8583	NIZORAL Approved Use Ketoconazole Cream, 2% is indicated for the topical treatment of tinea corporis, tinea cruris and tinea pedis caused by Trichophyton rubrum, T. mentagrophytes and Epidermophyton floccosum; in the treatment of tinea (pityriasis) versicolor caused by Malassezia furfur (Pityrosporum orbiculare); in the treatment of cutaneous candidiasis caused by Candida spp. and in the treatment of seborrheic dermatitis. Launch Date 1981
Cutaneous candidiasis 3 Sources: https://www.drugs.com/pro/ketoconazole-cream.html	Curative	Approved 8583	NIZORAL Approved Use Ketoconazole Cream, 2% is indicated for the topical treatment of tinea corporis, tinea cruris and tinea pedis caused by Trichophyton rubrum, T. mentagrophytes and Epidermophyton floccosum; in the treatment of tinea (pityriasis) versicolor caused by Malassezia furfur (Pityrosporum orbiculare); and in the treatment of cutaneous candidiasis caused by Candida spp. Launch Date 1981
Blastomycosis 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	Curative	Approved 8583	NIZORAL Tablets Approved Use NIZORAL Tablets should be used only when other effective antifungal therapy is not available or tolerated and the potential benefits are considered to outweigh the potential risks. NIZORAL (ketoconazole) Tablets are indicated for the treatment of the following systemic fungal infections in patients who have failed or who are intolerant to other therapies: blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. NIZORAL Tablets should not be used for fungal meningitis because it penetrates poorly into the cerebrospinal fluid. Launch Date 1981
Coccidioidomycosis 5 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	Curative	Approved 8583	NIZORAL Tablets Approved Use NIZORAL Tablets should be used only when other effective antifungal therapy is not available or tolerated and the potential benefits are considered to outweigh the potential risks. NIZORAL (ketoconazole) Tablets are indicated for the treatment of the following systemic fungal infections in patients who have failed or who are intolerant to other therapies: blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. NIZORAL Tablets should not be used for fungal meningitis because it penetrates poorly into the cerebrospinal fluid. Launch Date 1981
Cushing’s disease 13 Sources: http://adisinsight.springer.com/drugs/800037965 http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2016.NP.15.SAT-547	Primary	Phase III 665	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20047506 https://www.ncbi.nlm.nih.gov/pubmed/18640464	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6271723/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		KETOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.5 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		KETOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
1053 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6271723/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		KETOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
122 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6271723/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		KETOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		KETOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		KETOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

Doses

Dose	Population	Adverse events
400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3659003	unhealthy, 64.8 years (range: 52-80 years) Health Status: unhealthy Age Group: 64.8 years (range: 52-80 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3659003	Disc. AE: Gastrointestinal disorders, Gastrointestinal disorders... Other AEs: Itching, Dry skin... AEs leading to discontinuation/dose reduction: Gastrointestinal disorders (severe, 4 patients) Gastrointestinal disorders (severe, 3 patients) Other AEs: Itching (3 patients) Dry skin (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3659003
2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf	Other AEs: Application site burning, Headache... Other AEs: Application site burning (4.2%) Headache (1.1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	Other AEs: Hepatotoxicity... Other AEs: Hepatotoxicity (serious\|grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	Other AEs: QT interval prolonged... Other AEs: QT interval prolonged Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf

AEs

AE	Significance	Dose	Population
Dry skin	3 patients	400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3659003	unhealthy, 64.8 years (range: 52-80 years) Health Status: unhealthy Age Group: 64.8 years (range: 52-80 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3659003
Itching	3 patients	400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3659003	unhealthy, 64.8 years (range: 52-80 years) Health Status: unhealthy Age Group: 64.8 years (range: 52-80 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3659003
Gastrointestinal disorders	severe, 3 patients Disc. AE	400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3659003	unhealthy, 64.8 years (range: 52-80 years) Health Status: unhealthy Age Group: 64.8 years (range: 52-80 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3659003
Gastrointestinal disorders	severe, 4 patients Disc. AE	400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3659003	unhealthy, 64.8 years (range: 52-80 years) Health Status: unhealthy Age Group: 64.8 years (range: 52-80 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3659003
Headache	1.1%	2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf
Application site burning	4.2%	2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021946lbl.pdf
Hepatotoxicity	serious\|grade 5	200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf
QT interval prolonged		200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0035JB
A2B Chem	AB46343
Alfa Chemistry	ACM79156755
Ambeed	A183059
Angene	AGN-PC-0TG2VV
Bide Pharmatech	BD41921
BlocksMatrix Scientific	120008
Chem Scene	CS-0016830
Compound Cloud	47576
eMolecules	1987348
eMolecules	46100525
Enamine	EN300-1721056
Enamine	EN300-297716
eNovation Chemicals	D491426
Hairui	HR125788
Hairui	LEXM003
mcule	MCULE-4472529836
mcule	MCULE-7223272511
MedChem Express	HY-B0105B
Molcore	MC445166
MolPort	MolPort-006-167-686
MuseChem	A000489
NCI Plated 2007	317629
Norris Pharm	NSZB-A043550
TargetMol	T0679
Tetrahedron	TS73011
TimTec	ST51039034
Toronto Research Chemicals	K186020
Toronto Research Chemicals	K186025
ZINC	ZINC000000643153	http://zinc15.docking.org/substances/ZINC000000643153

PubMed

Title	Date	PubMed
Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.	2016-12-01	27789139
Updates on the role of adrenal steroidogenesis inhibitors in Cushing's syndrome: a focus on novel therapies.	2016-12	27600150
Ketoconazole Stereoisomers Differentially Induce Cytochrome P450 1A1 Between Human Hepatoma HepG2 and Mouse Hepatoma Hepa1c1c7 Cells.	2016-03	26886340
Highly potential antifungal activity of quantum-sized silver nanoparticles against Candida albicans.	2014-05	24648138
Otomycosis in the north of Iran: common pathogens and resistance to antifungal agents.	2014-05	23595615
Identification and antifungal susceptibility of fungi isolated from dermatomycoses.	2014-05	23556501
Synthesis, antifungal activities and molecular docking studies of novel 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates.	2014-03-03	24487187
Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents.	2014-03-03	24480358
Design, synthesis, antimicrobial activity and anti-HIV activity evaluation of novel hybrid quinazoline-triazine derivatives.	2014-02	23327639
Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents.	2014-01-01	24300736
Enantiospecific effects of ketoconazole on aryl hydrocarbon receptor.	2014	25000292
Hytramycins V and I, anti-Mycobacterium tuberculosis hexapeptides from a Streptomyces hygroscopicus strain.	2013-11-22	24224794
Antimicrobial ergosteroids and pyrrole derivatives from halotolerant Aspergillus flocculosus PT05-1 cultured in a hypersaline medium.	2013-11	24030481
3-Aryl-4-acyloxyethoxyfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: synthesis, molecular docking and antibacterial evaluation.	2013-09-01	23891164
Hippolachnin A, a new antifungal polyketide from the South China Sea sponge Hippospongia lachne.	2013-07-19	23829334
Synthesis and biological evaluation of pyrazoline derivatives bearing an indole moiety as new antimicrobial agents.	2013-06	23681942
Effects of chirality on the antifungal potency of methylated succinimides obtained by Aspergillus fumigatus biotransformations. comparison with racemic ones.	2013-05-15	23676473
Antifungal effect of ophthalmic preservatives phenylmercuric nitrate and benzalkonium chloride on ocular pathogenic filamentous fungi.	2013-01	23102555
Antibacterial and antifungal activities of polyketide metabolite from marine Streptomyces sp. AP-123 and its cytotoxic effect.	2013-01	22963878
Antimicrobial, antimycobacterial and antibiofilm properties of Couroupita guianensis Aubl. fruit extract.	2012-12-04	23206492
Antimicrobial aflatoxins from the marine-derived fungus Aspergillus flavus 092008.	2012-08	22941481
Ketoconazole enantiomer for the treatment of diabetes mellitus.	2010-02	20047506
Safety profile and metabolic effects of 14 days of treatment with DIO-902: results of a phase IIa multicenter, randomized, double-blind, placebo-controlled, parallel-group trial in patients with type 2 diabetes mellitus.	2008-06	18640464
Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers.	2007-02	17200836
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.	1998-05-21	9599237
In vitro activities of terbinafine against cutaneous isolates of Candida albicans and other pathogenic yeasts.	1998-05	9593126
Isolation and characterisation of an antifungal antibiotic (GR135402) with protein synthesis inhibition.	1998-01	9531986
In vitro antifungal activity of BMS-181184 against systemic isolates of Candida, Cryptococcus, and Blastomyces species.	1997-08	9327245
In vitro activity of a new pneumocandin antifungal, L-743,872, against azole-susceptible and -resistant Candida species.	1997-07	9210698
Multiple efflux mechanisms are involved in Candida albicans fluconazole resistance.	1996-12	9124851
In vitro antifungal and fungicidal activities and erythrocyte toxicities of cyclic lipodepsinonapeptides produced by Pseudomonas syringae pv. syringae.	1996-12	9124827
The effects of antifungal agents on the morphogenetic transformation by Candida albicans in vitro.	1996-10	8937953
In vitro synergistic activity of ketoconazole with valproic acid against Candida species.	1996-09	8876946
Antifungal activity of sertaconazole in vitro against clinical isolates of Candida spp..	1996-03-01	8697886
In vitro activity of a new pneumocandin antifungal agent, L-733,560 against azole-susceptible and -resistant Candida and Torulopsis species.	1995-12	8593003
In vitro susceptibility of filamentous fungi to itraconazole.	1995-10	9726141
Evaluation of water-soluble pneumocandin analogs L-733560, L-705589, and L-731373 with mouse models of disseminated aspergillosis, candidiasis, and cryptococcosis.	1995-05	7625792
In vitro activity of D0870 compared with those of other azoles against fluconazole-resistant Candida spp.	1995-04	7785986
Pneumocystis carinii is resistant to imidazole antifungal agents.	1994-08	7986021
Ro 09-1470 is a selective inhibitor of P-450 lanosterol C-14 demethylase of fungi.	1993-12	8109933
Effects of the combination of ketoconazole and calmodulin inhibitors against Candida albicans in vitro. Short communication.	1993-09	8240451
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.	1993-07	8369013
Antifungal properties in a novel series of triazino[5,6-b]indoles.	1993-06	8328776
Beta-cyanoglutamic acid, a new antifungal amino acid from a streptomycete.	1993-04	8501013
Stereoisomers of ketoconazole: preparation and biological activity.	1992-07-24	1495014
Cilofungin (LY121019), an antifungal agent with specific activity against Candida albicans and Candida tropicalis.	1988-09	3058017
Activity of SM-4470, a new imidazole derivative, against experimental fungal infections.	1986-09	3777903
In vitro activity of ketoconazole against herpes simplex virus.	1986-08	3021048
Activity of UK-49,858, a bis-triazole derivative, against experimental infections with Candida albicans and Trichophyton mentagrophytes.	1985-05	2990328
Antimycotic imidazoles. part 4. Synthesis and antifungal activity of ketoconazole, a new potent orally active broad-spectrum antifungal agent.	1979-08	490531

Patents

Sample Use Guides

In Vivo Use Guide

Subjects with type 2 diabetes who were between the ages of 18 and 70 years and were drug naive or receiving metformin at a stable dose were randomized to receive one of the following once daily at bedtime for 14 days: ketoconazole 400 mg; 2S,4R ketoconazole 200, 400, or 600 mg; or placebo. In a three period cross-over study in 24 healthy subjects dosed with placebo, 2S,4R ketoconazole or ketoconazole at a dose of 400mg QD.

Route of Administration: Oral

In Vitro Use Guide

30 or 50 uM 2S,4R ketoconazole induced CYP1A1 mRNA and protein in human HepG2 cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:02:14 GMT 2025` Edited by `admin` on `Mon Mar 31 19:02:14 GMT 2025`
Record UNII	R9400W927I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

KETOCONAZOLE

Official Name

English

J02AB02

Preferred Name

English

PIPERAZINE, 1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-, CIS-

Common Name

English

KETOCONAZOLE [MART.]

Common Name

English

R-41400

Code

English

KETOCONAZOLE [USAN]

Common Name

English

KETOCONAZOLE [MI]

Common Name

English

KETOCONAZOLE [EP MONOGRAPH]

Common Name

English

NSC-317629

Code

English

KETOCONAZOLE [EP IMPURITY]

Common Name

English

(±)-CIS-1-ACETYL-4-(P-((2-(2,4-DICHLOROPHENYL)-2-(IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE

Common Name

English

KETOCONAZOLE [USP MONOGRAPH]

Common Name

English

KETOCONAZOLE [USP-RS]

Common Name

English

R 41,400

Code

English

KETOZOLE

Brand Name

English

EXTINA

Brand Name

English

KETOCONAZOLE [JAN]

Common Name

English

KETOCONAZOLE [ORANGE BOOK]

Common Name

English

NIZORAL

Brand Name

English

ketoconazole [INN]

Common Name

English

Ketoconazole [WHO-DD]

Common Name

English

KETOCONAZOLE [USP IMPURITY]

Common Name

English

KETOCONAZOLE [VANDF]

Common Name

English

XOLEGEL

Brand Name

English

KETOCONAZOLE [HSDB]

Common Name

English

KETOCONAZOLUM [WHO-IP LATIN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG01AF11