Details of the Drug

General Information of Drug (ID: DMQ4TJK)

Drug Name

Dutasteride

Synonyms

Avodart; Avolve; Duagen; Dutasteride [USAN]; GG 745; GI 198745; Avidart (TN); Avodart (TN); Avodart, Dutasteride; Avolve (TN); Duagen (TN); Duprost (TN); Dutagen (TN); Dutas (TN); GG-745; GI-198745; GI-198745X; Dutasteride (JAN/USAN/INN); N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide; Alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide; (1S,3aS,3bS,5aR,9aR,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide; (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide; (5-alpha,17-beta)-N-{2,5 bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide;dutasteride; (5alpha,17beta)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Benign prostatic hyperplasia	GA90	Approved	[1]
Prostate adenocarcinoma	N.A.	Approved	[2]
Prostate cancer	2C82.0	Phase 3	[1]
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Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

528.5

Logarithm of the Partition Coefficient (xlogp)

5.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2-3 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability: The bioavailability of drug is 60% [3]
Clearance: The clearance of drug is 0.58 L/h [5]
Elimination: About 1-15% of the dose is excreted as the unchanged parent compound, while 2-90% of the total dose is excreted in the form of dutasteride-related metabolites in the feces [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 weeks [3]
Metabolism: The drug is metabolized via the hepatic [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.0135 micromolar/kg/day [6]
Vd: The volume of distribution (Vd) of drug is 300-500 L [3]

Chemical Identifiers

Formula: C27H30F6N2O2
IUPAC Name: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
Canonical SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CC[C@@H]5[C@@]3(C=CC(=O)N5)C
InChI: InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
InChIKey: JWJOTENAMICLJG-QWBYCMEYSA-N

Cross-matching ID

PubChem CID: 6918296
ChEBI ID: CHEBI:521033
CAS Number: 164656-23-9
DrugBank ID: DB01126
TTD ID: D0A9YA
INTEDE ID: DR0555
ACDINA ID: D00221

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Oxo-5-alpha-steroid 4-dehydrogenase (SRD5A)	TT2A0DR	S5A1_HUMAN ; S5A2_HUMAN ; PORED_HUMAN	Inhibitor	[7]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[8]
Cytochrome P450 3A5 (CYP3A5)_{Main DME}	DEIBDNY	CP3A5_HUMAN	Substrate	[9]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
17-beta-hydroxysteroid dehydrogenase type 1 (HSD17B1)	OT6EBDHM	DHB1_HUMAN	Gene/Protein Processing	[10]
17-beta-hydroxysteroid dehydrogenase type 3 (HSD17B3)	OT45D396	DHB3_HUMAN	Gene/Protein Processing	[10]
3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1)	OTQRET2B	S5A1_HUMAN	Gene/Protein Processing	[11]
3-oxo-5-alpha-steroid 4-dehydrogenase 2 (SRD5A2)	OTTG0NFD	S5A2_HUMAN	Gene/Protein Processing	[11]
Acireductone dioxygenase (ADI1)	OT8IOD03	MTND_HUMAN	Gene/Protein Processing	[12]
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[11]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[11]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Gene/Protein Processing	[11]
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[10]
Calreticulin (CALR)	OTYD2TR1	CALR_HUMAN	Gene/Protein Processing	[12]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Dronedarone	DMA8FS5	Moderate	Decreased metabolism of Dutasteride caused by Dronedarone mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[13]
Posaconazole	DMUL5EW	Moderate	Decreased metabolism of Dutasteride caused by Posaconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[13]
Dalfopristin	DM4LTKV	Moderate	Decreased metabolism of Dutasteride caused by Dalfopristin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[13]
Clarithromycin	DM4M1SG	Moderate	Decreased metabolism of Dutasteride caused by Clarithromycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[13]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Dutasteride caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[13]
Lapatinib	DM3BH1Y	Moderate	Decreased metabolism of Dutasteride caused by Lapatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Dutasteride caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
Palbociclib	DMD7L94	Moderate	Decreased metabolism of Dutasteride caused by Palbociclib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Dutasteride caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[13]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Dutasteride caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[13]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Dutasteride caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[13]
Nefazodone	DM4ZS8M	Moderate	Decreased metabolism of Dutasteride caused by Nefazodone mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[13]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Dutasteride caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[13]
Rufinamide	DMWE60C	Moderate	Increased metabolism of Dutasteride caused by Rufinamide mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[14]
Itraconazole	DMCR1MV	Moderate	Decreased metabolism of Dutasteride caused by Itraconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[13]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Dutasteride caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[13]
Telaprevir	DMMRV29	Moderate	Decreased metabolism of Dutasteride caused by Telaprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[13]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Dutasteride caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[15]
Fosamprenavir	DM4W9B3	Moderate	Decreased metabolism of Dutasteride caused by Fosamprenavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Dutasteride caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Saquinavir	DMG814N	Moderate	Decreased metabolism of Dutasteride caused by Saquinavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Etravirine	DMGV8QU	Moderate	Increased metabolism of Dutasteride caused by Etravirine mediated induction of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Darunavir	DMN3GCH	Moderate	Decreased metabolism of Dutasteride caused by Darunavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
BMS-201038	DMQTAGO	Moderate	Decreased metabolism of Dutasteride caused by BMS-201038 mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[13]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Dutasteride caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[13]
Suvorexant	DM0E6S3	Moderate	Decreased metabolism of Dutasteride caused by Suvorexant mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[13]
Crizotinib	DM4F29C	Moderate	Decreased metabolism of Dutasteride caused by Crizotinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[13]
Brigatinib	DM7W94S	Moderate	Increased metabolism of Dutasteride caused by Brigatinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[17]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Dutasteride caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[13]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Dutasteride caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[18]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Dutasteride caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[13]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Dutasteride caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[13]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Dutasteride caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[13]
Danazol	DML8KTN	Moderate	Decreased metabolism of Dutasteride caused by Danazol mediated inhibition of CYP450 enzyme.	Menstrual cycle bleeding disorder [GA20]	[13]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Dutasteride caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[19]
Nilotinib	DM7HXWT	Moderate	Decreased metabolism of Dutasteride caused by Nilotinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[13]
Dasatinib	DMJV2EK	Moderate	Decreased metabolism of Dutasteride caused by Dasatinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[13]
Netupitant	DMEKAYI	Moderate	Decreased metabolism of Dutasteride caused by Netupitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[13]
Entrectinib	DMMPTLH	Moderate	Decreased metabolism of Dutasteride caused by Entrectinib mediated inhibition of CYP450 enzyme.	Non-small cell lung cancer [2C25]	[13]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Dutasteride caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[13]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Dutasteride caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[20]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Dutasteride caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[21]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Dutasteride caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[13]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Dutasteride caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[22]
Bicalutamide	DMZMSPF	Moderate	Decreased metabolism of Dutasteride caused by Bicalutamide mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[13]
Temsirolimus	DMS104F	Moderate	Increased plasma concentrations of Dutasteride and Temsirolimus due to competitive inhibition of the same metabolic pathway.	Renal cell carcinoma [2C90]	[23]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Dutasteride caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[13]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Dutasteride caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[14]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Dutasteride caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[13]
Armodafinil	DMGB035	Minor	Increased metabolism of Dutasteride caused by Armodafinil mediated induction of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[24]
LEE011	DMMX75K	Moderate	Decreased metabolism of Dutasteride caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[13]
Brilinta	DMBR01X	Moderate	Decreased metabolism of Dutasteride caused by Brilinta mediated inhibition of CYP450 enzyme.	Thrombosis [DB61-GB90]	[13]
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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
Aminoethanoic acid	E00025	750	Buffering agent; Disintegrant; Lyophilization aid
Butylated hydroxytoluene	E00336	31404	Antioxidant
Caprylic acid	E00017	379	Emulsifying agent; Flavoring agent; Surfactant
FD&C blue no. 1	E00263	19700	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Kyselina citronova	E00014	311	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Glyceryl caprylate/caprate	E00616	91757308	Emollient; Emulsifying agent; Surfactant
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Medium-chain triglyceride	E00640	Not Available	Emollient; Lubricant; Surfactant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Dutasteride 0.5 mg capsule	0.5 mg	Oral Capsule	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7457).
2	Dutasteride FDA Label
3	FDA Approved Drug Products: AVODART (dutasteride) capsules
4	BDDCS applied to over 900 drugs
5	Gisleskog PO, Hermann D, Hammarlund-Udenaes M, Karlsson MO: The pharmacokinetic modelling of GI198745 (dutasteride), a compound with parallel linear and nonlinear elimination. Br J Clin Pharmacol. 1999 Jan;47(1):53-8.
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	The role of 5-alpha reductase inhibitors in prostate pathophysiology: Is there an additional advantage to inhibition of type 1 isoenzyme Can Urol Assoc J. 2009 Jun;3(3 Suppl 2):S109-14.
8	Duloxetine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2011 May;50(5):281-94.
9	Product monograph: Avodart (dutasteride capsules).
10	Effects of dutasteride on the expression of genes related to androgen metabolism and related pathway in human prostate cancer cell lines. Invest New Drugs. 2007 Oct;25(5):491-7.
11	Dutasteride affects progesterone metabolizing enzyme activity/expression in human breast cell lines resulting in suppression of cell proliferation and detachment. J Steroid Biochem Mol Biol. 2006 Aug;100(4-5):129-40.
12	Inhibition of 5alpha-reductase enhances testosterone-induced expression of U19/Eaf2 tumor suppressor during the regrowth of LNCaP xenograft tumor in nude mice. Prostate. 2010 Oct 1;70(14):1575-85. doi: 10.1002/pros.21193.
13	Product Information. Duagen (dutasteride). GlaxoSmithKline Healthcare, Pittsburgh, PA.
14	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
15	Product Information. Priftin (rifapentine). Hoechst Marion-Roussel Inc, Kansas City, MO.
16	Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
17	Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
18	Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
19	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
20	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
21	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
22	Benoist G, van Oort I, et al "Drug-drug interaction potential in men treated with enzalutamide: Mind the gap." Br J Clin Pharmacol 0 (2017): epub. [PMID: 28881501]
23	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
24	Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]