OralTopicalDosed ingredientTherapeutic flag Cosmetic cross-reference

Ketoconazole

CAS 65277-42-1

Ketoconazole (CAS 65277-42-1) is a Phase 4 pharmaceutical compound with 44 bioactivity targets and 592 adverse event associations.

SOURCE NLM DailyMed

Label records

SOURCE EMBL-EBI ChEMBL

Bioactivity

SOURCE DrugCentral

Adverse signals

592

SOURCE IUPHAR/BPS

PubMed IDs

SOURCE EMBL-EBI ChEMBL B25820EEF0F0

Compound Identity

Matched identifiers and naming fields for the pharmaceutical compound record.

Primary Name

Ketoconazole

CAS Number

65277-42-1

UNII

R9400W927I

InChIKey

XMAYWYJOQHXEEK-UHFFFAOYSA-N

ChEMBL ID

CHEMBL157101

Molecule Type

Small molecule

Source Match

EMBL-EBI ChEMBL (INCHIKEY)

black box warningdosed ingredientnatural productoraltherapeutic flagtopicalwithdrawn flag

SOURCE EMBL-EBI ChEMBL B25820EEF0F0

Clinical Development Phase

Highest clinical development phase rendered from the matched compound identifier rows.

Phase 4 (Approved)

Approved or marketed human pharmaceutical use is represented in the source phase field.

ChEMBL CHEMBL157101 | Small molecule

SOURCE Ingredients table / CosIng profile same-CAS cross-reference

Cross-Reference to Cosmetics

Same-CAS ingredient record found in the cosmetics vertical.

This substance also has a cosmetic safety profile →

SOURCE EMBL-EBI ChEMBL 61 bioactivity rows

Bioactivity & Target Interactions

Target-level activity records with assay counts, activity type, and measured value where present.

Target	Activity	Value	Assays	Organism
-	MIC	21.899877885714286 ug.mL-1	875	-
-	IC50	6698.840855263158 nM	439	-
-	MIC	121768.66744186047 nM	165	-
-	Potency	17876.327840909093 nM	109	-
-	AC50	15335.392156862745 nM	97	-
-	MIC	136.52047619047622 10'-2 umol/ml	63	-
-	GI50	31915.989491525423 nM	59	-
-	Ki	7108.555681818182 nM	40	-
-	Kd	6875.467733333334 nM	15	-
-	IC50	8.085 ug.mL-1	12	-
-	MIC	166.25 10'-2mmol/ml	8	-
-	MIC	9.375 ug	8	-
-	EC50	12308.825 nM	4	-
-	MIC	0.01 mg	1	-
Sodium/nucleoside cotransporter 1 Transporter	Ki	5.821	-	Homo sapiens
Alpha-2A adrenergic receptor GPCR	Ki	5.13	-	Homo sapiens
Potassium voltage-gated channel subfamily H member 2 Ion channel	IC50	5.72	-	Homo sapiens
Cytochrome P450 3A4 Enzyme	Ki	7	-	Homo sapiens
Multidrug resistance protein 1 Transporter	Ki	6	-	Homo sapiens
Sodium-dependent serotonin transporter Transporter	Ki	6.55	-	Homo sapiens
Sodium-dependent noradrenaline transporter Transporter	Ki	4.62	-	Homo sapiens
Alpha-2B adrenergic receptor GPCR	Ki	5.084	-	Homo sapiens
Histamine H2 receptor GPCR	Ki	4.667	-	Homo sapiens
Muscarinic acetylcholine receptor M2 GPCR	Ki	5.028	-	Homo sapiens
Aldehyde oxidase Enzyme	IC50	5.456	-	Homo sapiens
Sodium-dependent dopamine transporter Transporter	Ki	4.729	-	Homo sapiens
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor	-	-	-	Homo sapiens
Alpha-1D adrenergic receptor GPCR	Ki	4.84	-	Homo sapiens
Lanosterol 14-alpha demethylase Enzyme	IC50	7	-	Candida albicans (strain SC5314 / ATCC MYA-2876)
Delta-type opioid receptor GPCR	Ki	5.346	-	Homo sapiens
Bile salt export pump Transporter	IC50	5.54	-	Homo sapiens
Cytochrome P450 2C9 Enzyme	IC50	4.4	-	Homo sapiens
Aromatase Enzyme	Ki	6.4	-	Homo sapiens
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial Enzyme	IC50	6.47	-	Homo sapiens
Potassium voltage-gated channel subfamily A member 10 Ion channel	IC50	6.3	-	Homo sapiens
Cytochrome P450 2C19 Enzyme	IC50	4.72	-	Homo sapiens
Thromboxane-A synthase Enzyme	IC50	5.665	-	Homo sapiens
Lanosterol 14-alpha demethylase Enzyme	app Ki	7.197	-	Homo sapiens
Indoleamine 2,3-dioxygenase 1 Enzyme	IC50	4.6	-	Homo sapiens
Solute carrier family 22 member 1 Transporter	IC50	5.58	-	Homo sapiens
Substance-K receptor GPCR	Ki	5.24	-	Homo sapiens
Cytochrome P450 3A5 Enzyme	IC50	6.92	-	Homo sapiens
Arachidonate 15-lipoxygenase Enzyme	IC50	5.266	-	Oryctolagus cuniculus
Alpha-1B adrenergic receptor GPCR	Ki	4.897	-	Rattus norvegicus
5-hydroxytryptamine receptor 1B GPCR	Ki	5.211	-	Rattus norvegicus
Membrane-associated progesterone receptor component 1 Membrane receptor	Ki	5.009	-	Rattus norvegicus
Alpha-1A adrenergic receptor GPCR	IC50	4.45	-	Rattus norvegicus
Gonadotropin-releasing hormone receptor GPCR	Kd	9.66	-	Rattus norvegicus
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial Enzyme	IC50	6.506	-	Homo sapiens
Cytochrome P450 21 Enzyme	IC50	5.05	-	Homo sapiens

SOURCE DrugCentral 80 associations

Adverse Event Associations

DrugCentral / FAERS disproportionality signal rows matched to this compound.

Reaction PT	Drug AE	LLR	MedDRA
Psoriasis	203	207.462	10037153
Seborrhoeic dermatitis	37	104.916	10039793
Drug interaction	283	82.381	10013710
Product use in unapproved indication	206	63.137	10076476
Skin exfoliation	82	62.139	10040844
Endocrine ophthalmopathy	17	59.437	10060742
Eyelid disorder	23	58.924	10061130
Swelling of eyelid	26	55.356	10042690
Nasal ulcer	21	53.632	10028780
Adrenal insufficiency	53	52.356	10001367
Dermatitis atopic	37	51.767	10012438
Papule	32	50.976	10033733
Toxic shock syndrome	17	49.805	10044248
Cortisol increased	15	48.916	10011207
Product dose omission issue	197	48.264	10084406
Pruritus	254	45.276	10037087
Dermatitis	44	44.039	10012431
Contraindicated product administered	8	43.48	10078504
Prostatic specific antigen increased	31	39.241	10036975
Eczema	56	38.418	10014184
Systemic lupus erythematosus	7	38.157	10042945
Toxicity to various agents	39	36.59	10070863
Dry skin	73	36.247	10013786
Seborrhoeic keratosis	18	35.051	10039796
Glossodynia	6	32.89	10018388
Impetigo	15	32.68	10021531
Purpura senile	10	32.535	10037560
Infusion related reaction	23	32.501	10051792
Rhabdomyolysis	81	32.306	10039020
Tarsal tunnel syndrome	10	31.29	10043121
Mean cell haemoglobin increased	18	31.214	10026996
Drug ineffective for unapproved indication	56	30.948	10051118
Intertrigo	11	30.676	10022622
Therapeutic response unexpected	37	30.211	10043417
Drug abuse	4	29.587	10013654
Lower respiratory tract infection	5	28.349	10024968
Vitamin D decreased	25	27.43	10062189
Skin disorder	44	27.06	10040831
Colour vision tests normal	4	26.668	10010059
Hypothalamic pituitary adrenal axis suppression	8	26.537	10074052
Hypokalaemia	96	26.315	10021015
Contraindication to medical treatment	11	25.322	10010833
Melanocytic naevus	18	25.269	10027145
Guttate psoriasis	9	24.629	10018797
Pneumonia mycoplasmal	11	24.346	10035724
Xerosis	11	23.902	10048222
Eye infection	25	23.366	10015929
Dyslipidaemia	24	23.184	10058108
Anaplastic astrocytoma	6	22.334	10002224
Wound	11	22.126	10052428

Association rows are source-linked signal records, not incidence rates or clinical causality claims.

SOURCE IUPHAR/BPS 2 interactions

IUPHAR Ligand-Target Data

Curated ligand-target interaction rows with action, affinity, and literature identifiers.

Target	Action	Affinity	PubMed
CYP3A4 CYP3A4	Inhibition	7.0 pKi	25923589
K v 1.8 KCNA10	Channel blocker	6.3 pIC50	10836990

SOURCE PharmGKB 1 phenotype row

Pharmacogenomics

Drug-gene phenotype annotations and evidence levels from PharmGKB-mapped rows.

CYP3A5 (PA131) CYP3A5*1, CYP3A5*3

CYP3A5 *1/*1 + *1/*3 are associated with decreased severity of inhibition of CYP3A-catalyzed metabolism of midazolam or testosterone when treated with itraconazole or ketoconazole in Human Liver Microsomes as compared to CYP3A5 *3/*3.

Evidence: -; PMID 23723360

SOURCE NLM RxNorm 4 name rows

Drug Names / RxNorm

Normalized drug-name vocabulary rows, RxCUIs, and source abbreviations.

Name	RxCUI	Type	Source
ketoconazole	6135	SU	MTHSPL
Ketoconazole	6135	SU	MTHSPL
KETOCONAZOLE	6135	SU	MTHSPL
ketoconazole	6135	IN	RXNORM

SOURCE SIDER 80 side-effect rows

Side Effects

SIDER side-effect terms mapped to the drug or same-CAS compound identity.

Side Effect	Drug Name	MedDRA Type	Concept ID
Abdominal pain	ketoconazole	LLT	C0000737
Abdominal pain	ketoconazole	PT	C0000737
Abdominal pain upper	ketoconazole	LLT	C0232492
Abdominal pain upper	ketoconazole	PT	C0232492
Accidental exposure to product	ketoconazole	PT	C3544060
Accidental ingestion	ketoconazole	LLT	C0857807
Acute generalised exanthematous pustulosis	ketoconazole	LLT	C0877055
Acute generalised exanthematous pustulosis	ketoconazole	PT	C0877055
Alcohol intolerance	ketoconazole	LLT	C0151474
Alcohol intolerance	ketoconazole	PT	C0151474
Allergic conditions	ketoconazole	-	C0851444
Alopecia	ketoconazole	LLT	C0002170
Alopecia	ketoconazole	PT	C0002170
Anaphylactic shock	ketoconazole	LLT	C0002792
Anaphylactic shock	ketoconazole	PT	C0002792
Anaphylactic shock	ketoconazole	PT	C0002792
Anaphylactoid reaction	ketoconazole	LLT	C0340865
Anaphylactoid reaction	ketoconazole	PT	C0340865
Angioedema	ketoconazole	LLT	C0002994
Angioedema	ketoconazole	PT	C0002994
Angiopathy	ketoconazole	LLT	C0042373
Angiopathy	ketoconazole	PT	C0042373
Anorexia	ketoconazole	LLT	C0003123
Application site burn	ketoconazole	LLT	C0877661
Application site burn	ketoconazole	PT	C0877661
Application site pain	ketoconazole	PT	C0521491
Application site reaction	ketoconazole	LLT	C0151505
Application site reaction	ketoconazole	PT	C0151505
Arrhythmia	ketoconazole	LLT	C0003811
Arrhythmia	ketoconazole	PT	C0003811
Arthralgia	ketoconazole	LLT	C0003862
Arthralgia	ketoconazole	PT	C0003862
Asthenia	ketoconazole	LLT	C0004093
Asthenia	ketoconazole	PT	C0004093
Asthenia	ketoconazole	PT	C0004093
Azoospermia	ketoconazole	LLT	C0004509
Azoospermia	ketoconazole	PT	C0004509
Azoospermia	ketoconazole	PT	C0004509
Blood and lymphatic system disorders	ketoconazole	-	C0851353
Blood triglycerides increased	ketoconazole	PT	C0853692
Body temperature increased	ketoconazole	LLT	C0015967
Body temperature increased	ketoconazole	PT	C0015967
Breast disorder	ketoconazole	LLT	C0006145
Breast disorder	ketoconazole	PT	C0006145
Burning sensation	ketoconazole	LLT	C0085624
Burning sensation	ketoconazole	PT	C0085624
Chills	ketoconazole	LLT	C0085593
Chills	ketoconazole	PT	C0085593
Connective tissue disorder	ketoconazole	LLT	C0009782
Connective tissue disorder	ketoconazole	PT	C0009782
Constipation	ketoconazole	LLT	C0009806
Constipation	ketoconazole	PT	C0009806
Decreased appetite	ketoconazole	PT	C0232462
Dermatitis	ketoconazole	LLT	C0011603
Dermatitis	ketoconazole	PT	C0011603
Dermatitis	ketoconazole	PT	C0011603
Dermatitis contact	ketoconazole	LLT	C0011616
Dermatitis contact	ketoconazole	PT	C0011616
Dermatitis exfoliative	ketoconazole	LLT	C0011606
Dermatitis exfoliative	ketoconazole	PT	C0011606
Diarrhoea	ketoconazole	LLT	C0011991
Diarrhoea	ketoconazole	PT	C0011991
Discomfort	ketoconazole	PT	C0234215
Dizziness	ketoconazole	LLT	C0012833
Dizziness	ketoconazole	PT	C0012833
Dry eye	ketoconazole	PT	C0314719
Dry mouth	ketoconazole	LLT	C0043352
Dry mouth	ketoconazole	PT	C0043352
Dry skin	ketoconazole	LLT	C0151908
Dry skin	ketoconazole	PT	C0151908
Dysgeusia	ketoconazole	LLT	C0013378
Dysgeusia	ketoconazole	PT	C0013378
Dyspepsia	ketoconazole	LLT	C0013395
Dyspepsia	ketoconazole	PT	C0013395
Electrocardiogram QT prolonged	ketoconazole	LLT	C0151878
Electrocardiogram QT prolonged	ketoconazole	PT	C0151878
Endocrine disorder	ketoconazole	LLT	C0014130
Endocrine disorder	ketoconazole	PT	C0014130
Epistaxis	ketoconazole	LLT	C0014591
Epistaxis	ketoconazole	PT	C0014591

SOURCE Rendered pharma page rows FAQPage JSON-LD

Frequently Asked Questions

Short answers generated only from the same visible source-linked rows on this page.

What is Ketoconazole used for in pharmaceutical contexts?

Ketoconazole (CAS 65277-42-1) is rendered as a pharmaceutical compound from the matched source rows; no DailyMed product-name rows are present in this page query.

What are the known adverse events for Ketoconazole?

Ketoconazole has 592 DrugCentral/FAERS adverse event associations. Rendered reaction terms include Psoriasis, Seborrhoeic dermatitis, Drug interaction, Product use in unapproved indication, Skin exfoliation. Signal rows are source-linked records and should not be read as incidence rates or causality conclusions.

Is Ketoconazole also used in cosmetics?

Yes. The ingredients table has a same-CAS cosmetic profile for Ketoconazole with EU status "prohibited".

What clinical phase is Ketoconazole in?

Ketoconazole is rendered with ChEMBL max phase 4 (approved).

What bioactivity targets are documented for Ketoconazole?

Ketoconazole has 61 bioactivity rows in this page query. Rendered target entries include Sodium/nucleoside cotransporter 1, Alpha-2A adrenergic receptor, Potassium voltage-gated channel subfamily H member 2, Cytochrome P450 3A4, Multidrug resistance protein 1.