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ketoconazole 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
systemic antifungal agents, miconazole derivatives	1527	65277-42-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ketoconazole (+/-)-ketoconazole brizoral fungarest fungoral ketoderm ketoisdin ketozoral nizoral nizral panfungol ketoconazol R-41400	Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. Molecular weight: 531.43 Formula: C26H28Cl2N4O4 CLOGP: 3.44 LIPINSKI: 1 HAC: 8 HDO: 0 TPSA: 69.06 ALOGS: -4.76 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ketoconazole
(+/-)-ketoconazole
brizoral
fungarest
fungoral
ketoderm
ketoisdin
ketozoral
nizoral
nizral
panfungol
ketoconazol
R-41400

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

Molecular weight: 531.43
Formula: C26H28Cl2N4O4
CLOGP: 3.44
LIPINSKI: 1
HAC: 8
HDO: 0
TPSA: 69.06
ALOGS: -4.76
ROTB: 7

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.40	g	V
0.60	g	O
0.20	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	75 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	10.75 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	0.01 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
June 12, 1981	FDA	JANSSEN PHARMS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Psoriasis	168.76	13.14	138	12255	86819	63389810
Endocrine ophthalmopathy	65.86	13.14	17	12376	654	63475975
Swelling of eyelid	64.54	13.14	24	12369	3132	63473497
Toxic shock syndrome	62.04	13.14	17	12376	825	63475804
Eyelid disorder	56.68	13.14	19	12374	1830	63474799
Nasal ulcer	56.36	13.14	20	12373	2284	63474345
Seborrhoeic dermatitis	52.90	13.14	16	12377	1105	63475524
Product use in unapproved indication	52.44	13.14	111	12282	178969	63297660
Mean cell haemoglobin increased	44.59	13.14	18	12375	2925	63473704
Dermatitis atopic	38.81	13.14	24	12369	9700	63466929

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Psoriasis	53.29	13.27	63	10808	38749	34907311
Seborrhoeic dermatitis	49.51	13.27	19	10852	1689	34944371
Skin exfoliation	33.53	13.27	42	10829	27390	34918670
Pruritus	30.29	13.27	105	10766	141876	34804184
Prostatic specific antigen increased	29.21	13.27	29	10842	14651	34931409
Melanocytic naevus	28.11	13.27	14	10857	2330	34943730
Therapeutic response unexpected	26.64	13.27	23	10848	9734	34936326
Colour vision tests normal	25.53	13.27	4	10867	4	34946056
Toxicity to various agents	24.66	13.27	16	10855	200346	34745714
Anaplastic astrocytoma	24.52	13.27	6	10865	114	34945946

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Psoriasis	141.88	12.33	132	16985	89455	79637816
Endocrine ophthalmopathy	62.89	12.33	17	17100	711	79726560
Swelling of eyelid	61.33	12.33	25	17092	3786	79723485
Nasal ulcer	55.94	12.33	20	17097	2120	79725151
Toxic shock syndrome	53.82	12.33	17	17100	1232	79726039
Eyelid disorder	53.66	12.33	19	17098	1959	79725312
Cortisol increased	48.36	12.33	13	17104	532	79726739
Product dose omission issue	48.02	12.33	139	16978	247398	79479873
Seborrhoeic dermatitis	45.38	12.33	17	17100	2056	79725215
Dermatitis atopic	43.39	12.33	27	17090	10029	79717242

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	D01AC08	DERMATOLOGICALS ANTIFUNGALS FOR DERMATOLOGICAL USE ANTIFUNGALS FOR TOPICAL USE Imidazole and triazole derivatives
ATC	G01AF11	GENITO URINARY SYSTEM AND SEX HORMONES GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS Imidazole derivatives
ATC	H02CA03	SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS CORTICOSTEROIDS FOR SYSTEMIC USE ANTIADRENAL PREPARATIONS Anticorticosteroids
ATC	J02AB02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOTICS FOR SYSTEMIC USE ANTIMYCOTICS FOR SYSTEMIC USE Imidazole derivatives
FDA CS	M0002083	Azoles
FDA EPC	N0000175487	Azole Antifungal
FDA MoA	N0000182141	Cytochrome P450 3A4 Inhibitors
FDA MoA	N0000185503	P-Glycoprotein Inhibitors
FDA MoA	N0000190115	Cytochrome P450 3A5 Inhibitors
MeSH PA	D058888	14-alpha Demethylase Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Tinea pedis	indication	6020002	DOID:12403
Histoplasmosis	indication	12962009	DOID:1731
Hypercortisolism	indication	47270006
Candidiasis of skin	indication	49883006
Seborrheic dermatitis	indication	50563003	DOID:8741
Pityriasis versicolor	indication	56454009	DOID:9060
Paracoccidioidomycosis	indication	59925007	DOID:12662
Coccidioidomycosis	indication	60826002	DOID:13450
Blastomycosis	indication	69996000	DOID:12663
Disseminated candidiasis	indication	70572005

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	5.84	Basic
pKa2	3.5	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Steroid 17-alpha-hydroxylase/17,20 lyase	Enzyme	P05093	CP17A_HUMAN	INHIBITOR	IC50	7.28	WOMBAT-PK	DRUG LABEL
Cytochrome P450 11B1, mitochondrial	Enzyme	P15538	C11B1_HUMAN	INHIBITOR	IC50	6.90	SCIENTIFIC LITERATURE	DRUG LABEL
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		Ki	7	WOMBAT-PK
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		Ki	6	WOMBAT-PK
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	6.55	DRUG MATRIX
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	4.62	DRUG MATRIX
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	5.08	DRUG MATRIX
Histamine H2 receptor	GPCR	P25021	HRH2_HUMAN		Ki	4.67	DRUG MATRIX
Muscarinic acetylcholine receptor M2	GPCR	P08172	ACM2_HUMAN		Ki	5.03	DRUG MATRIX
Aldehyde oxidase	Enzyme	Q06278	AOXA_HUMAN		IC50	5.46	WOMBAT-PK

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External reference:

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ID	Source
KTN	PDB_CHEM_ID
002903	NDDF
202692	RXNORM
2568	IUPHAR_LIGAND_ID
2701	MMSL
31001	MMSL
387216007	SNOMEDCT_US
4019271	VUID
4019271	VANDF
40232005	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
EXTINA	HUMAN PRESCRIPTION DRUG LABEL	1	0378-8136	AEROSOL, FOAM	20 mg	TOPICAL	NDA	25 sections
Ketaconazole	HUMAN PRESCRIPTION DRUG LABEL	1	0378-7007	AEROSOL, FOAM	20 mg	TOPICAL	NDA authorized generic	26 sections
Ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	0093-3219	CREAM	20 mg	TOPICAL	ANDA	17 sections
ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	0168-0099	CREAM	20 mg	TOPICAL	ANDA	16 sections
KETOCONAZOLE	HUMAN PRESCRIPTION DRUG LABEL	1	16590-998	TABLET	200 mg	ORAL	ANDA	22 sections
Ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	16714-955	CREAM	20 mg	TOPICAL	ANDA	18 sections
Ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	21695-554	CREAM	20 mg	TOPICAL	ANDA	19 sections
Ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	21695-555	CREAM	20 mg	TOPICAL	ANDA	19 sections
Ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	21695-556	CREAM	20 mg	TOPICAL	ANDA	19 sections
Ketoconazole	HUMAN PRESCRIPTION DRUG LABEL	1	21695-562	TABLET	200 mg	ORAL	ANDA	23 sections

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