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=C(Cl)C=C(Cl)C=C5)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/25775613 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018533s041lbl.pdf | https://www.drugbank.ca/drugs/DB01026https://www.ncbi.nlm.nih.gov/pubmed/27600150
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

2S,4R ketoconazole or levoketoconazole is the 2S,4R enantiomer of ketoconazole, purified from racemic ketoconazole. Both enantiomers exerts antifungal activity. Ketoconazole activates AhR in gene reporter cell line and dose-dependently induces CYP1A1 mRNA and CYP1A1 protein in HepG2 cells, with enantiospecific pattern, i.e. 2R,4S ketoconazole was much more active as compared to 2S,4R ketoconazole. Levoketoconazole was shown to be a more potent inhibitor than the 2R,4S enantiomer of several enzymes in the steroidogenic pathway (CYP11B1, CYP17 and CYP21). Levoketoconazole was tested for the treatment of endogenous Cushing’s syndrome (Phase III) and type 2 diabetes mellitus (Phase II).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Aryl hydrocarbon receptor 26 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25000292	Agonist 2678	2.2 µM [EC50]
Aryl hydrocarbon receptor 26 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25000292	Antagonist 2778	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 8297	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 8297	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 8297	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 8297	27.0 nM [Kd]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26614990	Inhibitor 8297	0.18 µM [IC50]
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1526623	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Tinea corporis 19 Sources: https://www.drugs.com/cdi/ketoconazole-cream.html	Curative	Approved 8429	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 8429	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 8429	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 8429	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 8429	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 656	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20047506 https://www.ncbi.nlm.nih.gov/pubmed/18640464	Primary	Phase II 1132	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) n = 28 Health Status: unhealthy Condition: relapsing prostatic cancer Age Group: 64.8 years (range: 52-80 years) Sex: M Population Size: 28 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 n = 545 Health Status: unhealthy Condition: seborhheic dermatitis Age Group: adult Population Size: 545 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 Co-administed with:: dofetilide 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) n = 28 Health Status: unhealthy Condition: relapsing prostatic cancer Age Group: 64.8 years (range: 52-80 years) Sex: M Population Size: 28 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) n = 28 Health Status: unhealthy Condition: relapsing prostatic cancer Age Group: 64.8 years (range: 52-80 years) Sex: M Population Size: 28 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) n = 28 Health Status: unhealthy Condition: relapsing prostatic cancer Age Group: 64.8 years (range: 52-80 years) Sex: M Population Size: 28 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) n = 28 Health Status: unhealthy Condition: relapsing prostatic cancer Age Group: 64.8 years (range: 52-80 years) Sex: M Population Size: 28 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 n = 545 Health Status: unhealthy Condition: seborhheic dermatitis Age Group: adult Population Size: 545 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 n = 545 Health Status: unhealthy Condition: seborhheic dermatitis Age Group: adult Population Size: 545 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 Co-administed with:: dofetilide 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
Enamine	EN300-1721056
Enamine	EN300-297716
Hairui	HR125788
Hairui	LEXM003
MedChem Express	HY-B0105B
MolPort	MolPort-006-167-686
Molcore	MC445166
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
eMolecules	1987348
eMolecules	46100525
eNovation Chemicals	D491426
mcule	MCULE-4472529836
mcule	MCULE-7223272511

PubMed

Title	Date	PubMed
Activity of SM-4470, a new imidazole derivative, against experimental fungal infections.	1986 Sep	3777903
Cilofungin (LY121019), an antifungal agent with specific activity against Candida albicans and Candida tropicalis.	1988 Sep	3058017
Pradimicins A, B and C: new antifungal antibiotics. II. In vitro and in vivo biological activities.	1990 Jul	2167304
In vitro studies of activities of some antifungal agents against Candida albicans ATCC 10231 by the turbidimetric method.	1992 Apr	1503456
In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.	1992 Apr	1406898
Beta-cyanoglutamic acid, a new antifungal amino acid from a streptomycete.	1993 Apr	8501013
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.	1993 Jul	8369013
Antifungal properties in a novel series of triazino[5,6-b]indoles.	1993 Jun	8328776
Effects of the combination of ketoconazole and calmodulin inhibitors against Candida albicans in vitro. Short communication.	1993 Sep	8240451
In vitro activity of a new pneumocandin antifungal agent, L-733,560 against azole-susceptible and -resistant Candida and Torulopsis species.	1995 Dec	8593003
In vitro susceptibility of filamentous fungi to itraconazole.	1995 Oct	9726141
Multiple efflux mechanisms are involved in Candida albicans fluconazole resistance.	1996 Dec	9124851
In vitro antifungal and fungicidal activities and erythrocyte toxicities of cyclic lipodepsinonapeptides produced by Pseudomonas syringae pv. syringae.	1996 Dec	9124827
Antifungal activity of sertaconazole in vitro against clinical isolates of Candida spp.	1996 Mar-Apr	8697886
The effects of antifungal agents on the morphogenetic transformation by Candida albicans in vitro.	1996 Oct	8937953
In vitro synergistic activity of ketoconazole with valproic acid against Candida species.	1996 Sep	8876946
In vitro antifungal activity of BMS-181184 against systemic isolates of Candida, Cryptococcus, and Blastomyces species.	1997 Aug	9327245
In vitro activity of a new pneumocandin antifungal, L-743,872, against azole-susceptible and -resistant Candida species.	1997 Jul	9210698
Isolation and characterisation of an antifungal antibiotic (GR135402) with protein synthesis inhibition.	1998 Jan	9531986
In vitro activities of terbinafine against cutaneous isolates of Candida albicans and other pathogenic yeasts.	1998 May	9593126
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.	1998 May 21	9599237
3-Phenyl-5-methyl-2H,5H-furan-2-ones: tuning antifungal activity by varying substituents on the phenyl ring.	2000 Aug 21	10969993
Synthesis and antimicrobial activities of some 3-arylamino-5-[2-(substituted 1-imidazolyl)ethyl]-1,2,4-triazole derivatives.	2000 Nov	11137231
Activity of voriconazole against Candida albicans and Candida krusei isolated since 1984.	2000 Nov	11091037
Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis.	2000 Nov 15	11064188
Azasordarins: susceptibility of fluconazole-susceptible and fluconazole-resistant clinical isolates of Candida spp. to GW 471558.	2001 Jun	11353650
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.	2001 Jun 15	11377375
Antimicrobial activities of a new schizozygane indoline alkaloid from Schizozygia coffaeoides and the revised structure of isoschizogaline.	2002 Apr	11975502
Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates.	2002 Nov	12431873
Pharmacokinetics and interactions of a novel antagonist of chemokine receptor 5 (CCR5) with ritonavir in rats and monkeys: role of CYP3A and P-glycoprotein.	2003 Mar	12604693
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Synthesis and SAR studies of biaryloxy-substituted triazoles as antifungal agents.	2008 Jun 1	18467095
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009 Feb	19014974
In vitro investigation of antifungal activity of allicin alone and in combination with azoles against Candida species.	2010 Apr	19924565
Synergistic anticandidal activity of pure polyphenol curcumin I in combination with azoles and polyenes generates reactive oxygen species leading to apoptosis.	2010 Aug 1	20528949
Synthesis and the selective antifungal activity of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine derivatives.	2010 May	20106559
Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives.	2011 Jul	21420761
Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones.	2011 Jul 1	21621411
Comparison of the effect of non-antifungal and antifungal agents on Candida isolates from the gastrointestinal tract.	2012 Jan	22208440
Effect of pH on in vitro susceptibility of Candida glabrata and Candida albicans to 11 antifungal agents and implications for clinical use.	2012 Mar	22232293
Antibacterial and antifungal activities of polyketide metabolite from marine Streptomyces sp. AP-123 and its cytotoxic effect.	2013 Jan	22963878
Hippolachnin A, a new antifungal polyketide from the South China Sea sponge Hippospongia lachne.	2013 Jul 19	23829334
Antimicrobial ergosteroids and pyrrole derivatives from halotolerant Aspergillus flocculosus PT05-1 cultured in a hypersaline medium.	2013 Nov	24030481
Hytramycins V and I, anti-Mycobacterium tuberculosis hexapeptides from a Streptomyces hygroscopicus strain.	2013 Nov 22	24224794
3-Aryl-4-acyloxyethoxyfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: synthesis, molecular docking and antibacterial evaluation.	2013 Sep 1	23891164
Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents.	2014 Jan 1	24300736
Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents.	2014 Mar 3	24480358
Highly potential antifungal activity of quantum-sized silver nanoparticles against Candida albicans.	2014 May	24648138
Otomycosis in the north of Iran: common pathogens and resistance to antifungal agents.	2014 May	23595615
Identification and antifungal susceptibility of fungi isolated from dermatomycoses.	2014 May	23556501

Patents

Sample Use Guides

In Vivo Use Guide

The recommended starting dose of NIZORAL (ketoconazole) Tablets is a single daily administration of 200 mg (one tablet). If clinical responsiveness is insufficient within the expected time, the dose of NIZORAL Tablets may be increased to 400 mg (two tablets) once daily

Route of Administration: Oral

In Vitro Use Guide

In the case of ketoconazole, 50% inhibition of E. floccosum growth was achieved at 100 mg/L while 100% inhibition of growth was achieved at 200 mg/L. Ketoconazole was found to inhibit the growth of E. floccosum at 0.003-1.700 mg/L and was fungicidal at concentrations ranging from 0.027-1.700 mg/L.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:05:27 GMT 2023` Edited by `admin` on `Fri Dec 15 18:05:27 GMT 2023`
Record UNII	R9400W927I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KETOCONAZOLE

Official 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

KETOCONAZOLE [INCI]

Common Name

English

NSC-317629

Code

English

J02AB02

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