Details of the Drug

General Information of Drug (ID: DML8KTN)

Drug Name

Danazol

Synonyms

Anatrol; Chronogyn; Cyclomen; Danatrol; Danazant; Danazole; Danazolum; Danocrine; Danogen; Danokrin; Danol; Danoval; Danzol; Ladogal; Norciden; Panacrine; Winobanin; Alphapharm Brand of Danazol; Antigen Brand of Danazol; Kendrick Brand of Danazol; Ratiopharm Brand of Danazol; Sanofi Brand of Danazol; Sanofi Synthelabo Brand ofDanazol; Sanofi Winthrop Brand of Danazol; WIN 17757; Danazol-ratiopharm; Danazolum [INN-Latin]; Danocrine (TN); WIN 17,757; WIN-17757; Win 17, 757; Danazol (JAN/USP/INN); Danazol [USAN:BAN:INN:JAN];[1,2]oxazolo[4',5':2,3]-17alpha-pregn-4-en-20-yn-17-ol; (1R,3aS,3bR,10aR,10bS,12aS)-1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol; (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol; 1-Ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol; 17-alpha-2,4-Pregnadien-20-yno(2,3-d)isoxazol-17-ol; 17-alpha-Pregn-4-en-20-yno(2,3-d)isoxazol-17-ol; 17-alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol; 17.Alpha.-Pregna-2, {4-dien-20-yno[2,3-d]isoxazol-17-ol}; 17alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol

Indication

Disease Entry	ICD 11	Status	REF
Menorrhagia	GA20.50	Approved	[1], [2]
Breast cancer	2C60-2C65	Phase 2	[1], [3]

Therapeutic Class

Fertility Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

337.5

Topological Polar Surface Area (xlogp)

3.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 15.71 mL/min/kg [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 24 hours [5]
Metabolism: The drug is metabolized via the hepatic [6]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 33.78225 micromolar/kg/day [7]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 5.18 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 0.0009 mg/mL [4]

Chemical Identifiers

Formula: C22H27NO2
IUPAC Name: (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
Canonical SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5
InChI: InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
InChIKey: POZRVZJJTULAOH-LHZXLZLDSA-N

Cross-matching ID

PubChem CID: 28417
ChEBI ID: CHEBI:4315
CAS Number: 17230-88-5
DrugBank ID: DB01406
TTD ID: D09IPV
INTEDE ID: DR2401
ACDINA ID: D00165

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Estrogen receptor (ESR)	TTZAYWL	ESR1_HUMAN	Antagonist	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Menorrhagia

ICD Disease Classification

GA20.50

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Estrogen receptor (ESR)	DTT	ESR1	2.05E-08	-0.08	-0.31

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Danazol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[16]
Midostaurin	DMI6E0R	Moderate	Decreased metabolism of Danazol caused by Midostaurin mediated inhibition of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[17]
Gilteritinib	DMWQ4MZ	Moderate	Decreased metabolism of Danazol caused by Gilteritinib mediated inhibition of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[18]
Ivabradine	DM0L594	Moderate	Decreased metabolism of Danazol caused by Ivabradine mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[18]
Dronedarone	DMA8FS5	Moderate	Decreased metabolism of Danazol caused by Dronedarone mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[19]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[20]
Cariprazine	DMJYDVK	Moderate	Decreased metabolism of Danazol caused by Cariprazine mediated inhibition of CYP450 enzyme.	Bipolar disorder [6A60]	[18]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Danazol and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[21]
Ixabepilone	DM2OZ3G	Moderate	Decreased metabolism of Danazol caused by Ixabepilone mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[22]
Palbociclib	DMD7L94	Moderate	Decreased metabolism of Danazol caused by Palbociclib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[18]
Bosutinib	DMTI8YE	Moderate	Decreased metabolism of Danazol caused by Bosutinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[18]
Macitentan	DMP79A1	Moderate	Decreased metabolism of Danazol caused by Macitentan mediated inhibition of CYP450 enzyme.	Cardiovascular disease [BA00-BE2Z]	[23]
PF-04449913	DMSB068	Moderate	Decreased metabolism of Danazol caused by PF-04449913 mediated inhibition of CYP450 enzyme.	Chronic myelomonocytic leukaemia [2A40]	[24]
Indacaterol	DMQJHR7	Minor	Decreased metabolism of Danazol caused by Indacaterol mediated inhibition of CYP450 enzyme.	Chronic obstructive pulmonary disease [CA22]	[25]
Ulipristal	DMBNI20	Minor	Decreased metabolism of Danazol caused by Ulipristal mediated inhibition of CYP450 enzyme.	Contraceptive management [QA21]	[18]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Danazol caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[18]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Danazol caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[26]
Vilazodone	DM4LECQ	Moderate	Decreased metabolism of Danazol caused by Vilazodone mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[27]
Polatuzumab vedotin	DMF6Y0L	Moderate	Decreased metabolism of Danazol caused by Polatuzumab vedotin mediated inhibition of CYP450 enzyme.	Diffuse large B-cell lymphoma [2A81]	[28]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Danazol caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[18]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Cannabidiol.	Epileptic encephalopathy [8A62]	[18]
Tazemetostat	DMWP1BH	Moderate	Decreased metabolism of Danazol caused by Tazemetostat mediated inhibition of CYP450 enzyme.	Follicular lymphoma [2A80]	[29]
Mirabegron	DMS1GYT	Minor	Decreased metabolism of Danazol caused by Mirabegron mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[30]
Ripretinib	DM958QB	Moderate	Decreased metabolism of Danazol caused by Ripretinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[16]
Avapritinib	DMK2GZX	Moderate	Decreased metabolism of Danazol caused by Avapritinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[18]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[31]
MK-1439	DM215WE	Minor	Decreased metabolism of Danazol caused by MK-1439 mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[32]
Dolutegravir	DMCZGRE	Minor	Decreased metabolism of Danazol caused by Dolutegravir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[33]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Danazol caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[34]
Lopinavir	DMITQS0	Minor	Decreased metabolism of Danazol caused by Lopinavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[18]
Rilpivirine	DMJ0QOW	Moderate	Decreased metabolism of Danazol caused by Rilpivirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Maraviroc	DMTL94F	Moderate	Decreased metabolism of Danazol caused by Maraviroc mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Danazol and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[36]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Danazol and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[37]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Danazol and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[38]
Suvorexant	DM0E6S3	Moderate	Decreased metabolism of Danazol caused by Suvorexant mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[16]
ITI-007	DMUQ1DO	Moderate	Decreased metabolism of Danazol caused by ITI-007 mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[39]
Naloxegol	DML0B41	Major	Decreased metabolism of Danazol caused by Naloxegol mediated inhibition of CYP450 enzyme.	Large intestine motility disorder [DB32]	[18]
Pemigatinib	DM819JF	Moderate	Decreased metabolism of Danazol caused by Pemigatinib mediated inhibition of CYP450 enzyme.	Liver cancer [2C12]	[18]
Crizotinib	DM4F29C	Moderate	Decreased metabolism of Danazol caused by Crizotinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[40]
Brigatinib	DM7W94S	Moderate	Decreased metabolism of Danazol caused by Brigatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[16]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Danazol caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[41]
Lurbinectedin	DMEFRTZ	Moderate	Decreased metabolism of Danazol caused by Lurbinectedin mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[42]
PF-06463922	DMKM7EW	Moderate	Decreased metabolism of Danazol caused by PF-06463922 mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[43]
Osimertinib	DMRJLAT	Moderate	Decreased metabolism of Danazol caused by Osimertinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[44]
Pralsetinib	DMWU0I2	Moderate	Decreased metabolism of Danazol caused by Pralsetinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[45]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Danazol caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[18]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[46]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Idelalisib.	Mature B-cell leukaemia [2A82]	[47]
GDC-0199	DMH0QKA	Moderate	Decreased metabolism of Danazol caused by GDC-0199 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[16]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Danazol caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[48]
Acalabrutinib	DM7GCVW	Moderate	Decreased metabolism of Danazol caused by Acalabrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[49]
Ibrutinib	DMHZCPO	Moderate	Decreased metabolism of Danazol caused by Ibrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[50]
Selumetinib	DMC7W6R	Moderate	Decreased metabolism of Danazol caused by Selumetinib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[51]
Ubrogepant	DM749I3	Moderate	Decreased metabolism of Danazol caused by Ubrogepant mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[52]
Flibanserin	DM70DTN	Moderate	Decreased metabolism of Danazol caused by Flibanserin mediated inhibition of CYP450 enzyme.	Mood disorder [6A60-6E23]	[53]
Carfilzomib	DM48K0X	Major	Additive thrombogenic effects by the combination of Danazol and Carfilzomib.	Multiple myeloma [2A83]	[16]
Panobinostat	DM58WKG	Moderate	Decreased metabolism of Danazol caused by Panobinostat mediated inhibition of CYP450 enzyme.	Multiple myeloma [2A83]	[54]
Nilotinib	DM7HXWT	Moderate	Decreased metabolism of Danazol caused by Nilotinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[55]
Ruxolitinib	DM7Q98D	Minor	Decreased metabolism of Danazol caused by Ruxolitinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[18]
Entrectinib	DMMPTLH	Moderate	Decreased metabolism of Danazol caused by Entrectinib mediated inhibition of CYP450 enzyme.	Non-small cell lung cancer [2C25]	[56]
Olaparib	DM8QB1D	Moderate	Decreased metabolism of Danazol caused by Olaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[57]
Pimavanserin	DMR7IVC	Moderate	Decreased metabolism of Danazol caused by Pimavanserin mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[58]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Danazol caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[59]
Lonafarnib	DMGM2Z6	Major	Decreased metabolism of Danazol caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[60]
Enzalutamide	DMGL19D	Moderate	Decreased metabolism of Danazol caused by Enzalutamide mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[61]
Silodosin	DMJSBT6	Moderate	Decreased metabolism of Danazol caused by Silodosin mediated inhibition of CYP450 enzyme.	Prostate hyperplasia [GA90]	[62]
Everolimus	DM8X2EH	Moderate	Decreased metabolism of Danazol caused by Everolimus mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[63]
Axitinib	DMGVH6N	Moderate	Decreased metabolism of Danazol caused by Axitinib mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[18]
Temsirolimus	DMS104F	Moderate	Decreased metabolism of Danazol caused by Temsirolimus mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[64]
LDE225	DMM9F25	Moderate	Decreased metabolism of Danazol caused by LDE225 mediated inhibition of CYP450 enzyme.	Skin cancer [2C30-2C37]	[65]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Danazol caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[16]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Danazol and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[18]
Armodafinil	DMGB035	Minor	Decreased metabolism of Danazol caused by Armodafinil mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[16]
LEE011	DMMX75K	Moderate	Decreased metabolism of Danazol caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[16]
Elagolix	DMB2C0E	Moderate	Decreased metabolism of Danazol caused by Elagolix mediated inhibition of CYP450 enzyme.	Uterine fibroid [2E86]	[66]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 28	E00491	6097185	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 16 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Danazol 200 mg capsule	200 mg	Oral Capsule	Oral
Danazol 100 mg capsule	100 mg	Oral Capsule	Oral
Danazol 50 mg capsule	50 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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57	Product Information. Lynparza (olaparib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
58	Product Information. Nuplazid (pimavanserin). Accelis Pharma, East Windsor, NJ.
59	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
60	Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
61	Product Information. Xtandi (enzalutamide). Astellas Pharma US, Inc, Deerfield, IL.
62	Product Information. Rapaflo (silodosin). Watson Pharmaceuticals, Corona, CA.
63	Product Information. Afinitor (everolimus). Novartis Pharmaceuticals, East Hanover, NJ.
64	Product Information. Torisel (temsirolimus). Wyeth-Ayerst Laboratories, Philadelphia, PA.
65	Product Information. Odomzo (sonidegib). Novartis Pharmaceuticals, East Hanover, NJ.
66	Product Information. Orilissa (elagolix). AbbVie US LLC, North Chicago, IL.