Details of the Drug

General Information of Drug (ID: DMWV3TZ)

• Drug Name: Finasteride
• Synonyms: Andozac; Eucoprost; FIT; Finasterida; Finasteridum; Finastid; Finpecia; Propecia; Propeshia; Proscar; Prostide; Cahill May Roberts Brand of Finasteride; Chibro Proscar; Frosst Iberica Brand of Finasteride; Lipha Brand of Finasteride; MSD Brand of Finasteride; MSD Chibropharm Brand of Finasteride; MK 0906; MK 906; MK906; Merck Brand 1 of Finasteride; Merck Brand 2 of Finasteride; Merck Frosst Brand 1 of Finasteride; Merck Frosst Brand 2 of Finasteride; Alternova (TN); Appecia (TN); Chibro-Proscar; Finalo (TN); Finara (TN); Finast (TN); Finasterid (TN); Finasterid IVAX (TN); Finasterida [INN-Spanish]; Finasteridum [INN-Latin]; Finax (TN); Fincar (TN); Finpecia (TN); Gefina (TN); KS-1058; MK-0906; MK-906; Merck Sharp & Dhome Brand 2 of Finasteride; Merck Sharp & Dohme Brand 1 of Finasteride; Propecia (TN); Proscar (TN); Prosteride (TN); YM-152; Finasteride (USP/INN); Finasteride [USAN:INN:BAN]; L-652,931; Proscar, Propecia, Finasteride; N-tert-Butyl-3-oxo-4-aza-5alpha-androst-1-en-17beta-carboxamide; N-tert-Butyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide; N-(2-methyl-2-propyl)-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide; N-(2-Methyl-2-propyl)-3-oxo-4-aza-5-alpha-androst-1-ene-17-beta-carboxamide; (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide; (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(1,1-dimethylethyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide; (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(tert-butyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide; (5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide; 17beta-(N-tert-butylcarbamoyl)-4-aza-5 alpha-androst-1-en-3-one

Indication

Disease Entry	ICD 11	Status	REF
Benign prostatic hyperplasia	GA90	Approved	[1], [2]

• Therapeutic Class: Antihyperplasia Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 372.5
  Topological Polar Surface Area (xlogp); 3
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 2
• ADMET Property:
  Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 53 mcgh/L [3]
  Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 37 mcg/L [3]
  Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1-2 h [3]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
  Bioavailability: The bioavailability of drug is 65% [3]
  Clearance: The clearance of drug is 70-279 mL/min [5]
  Elimination: In healthy subjects, about 32-46% of total oral dose of finasteride was excreted in the urine in the form of metabolites while about 51-64% of the dose was excreted in the feces [5]
  Half-life: The concentration or amount of drug in body reduced by one-half in 3 - 6 hours (in healthy young subjects), and 8 hours (in elderly patients over the age of 70 years) [5]
  Metabolism: The drug is metabolized via the hepatic [5]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.19173 micromolar/kg/day [6]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.095% [7]
  Vd: The volume of distribution (Vd) of drug is 76 L [5]
  Water Solubility: The ability of drug to dissolve in water is measured as 0.043 mg/mL [4]
• Chemical Identifiers:
  Formula: C23H36N2O2
  IUPAC Name: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-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)NC(C)(C)C)CC[C@@H]4[C@@]3(C=CC(=O)N4)C
  InChI: InChI=1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
  InChIKey: DBEPLOCGEIEOCV-WSBQPABSSA-N
• Cross-matching ID:
  PubChem CID: 57363
  ChEBI ID: CHEBI:5062
  CAS Number: 98319-26-7
  DrugBank ID: DB01216
  TTD ID: D08IWD
  INTEDE ID: DR0695
  ACDINA ID: D00275

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	[8]
Steroid 5-alpha-reductase 2 (SRD5A2)	TTT02K8	S5A2_HUMAN	Inhibitor	[9]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4) Main DME	DE4LYSA	CP3A4_HUMAN	Substrate	[10]
Cytochrome P450 3A5 (CYP3A5)	DEIBDNY	CP3A5_HUMAN	Substrate	[11]
Cytochrome P450 3A7 (CYP3A7)	DERD86B	CP3A7_HUMAN	Substrate	[11]

Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Saquinavir	DMG814N	Moderate	Decreased metabolism of Finasteride caused by Saquinavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[44]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Finasteride caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[45]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Finasteride caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[46]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Finasteride caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[47]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Finasteride caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[48]
Temsirolimus	DMS104F	Moderate	Increased plasma concentrations of Finasteride and Temsirolimus due to competitive inhibition of the same metabolic pathway.	Renal cell carcinoma [2C90]	[49]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Finasteride caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[50]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Finasteride caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[51]

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
Docusate sodium	E00563	23673837	Surfactant
FD&C blue no. 2	E00446	2723854	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Finasteride 1 mg tablet	1 mg	Oral Tablet	Oral
Finasteride 5 mg tablet	5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

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: 6818).
• [2] Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
• [3] FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
• [4] BDDCS applied to over 900 drugs
• [5] FDA Approved Drug Products: PROSCAR (finasteride) tablets
• [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] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [8] 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.
• [9] Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
• [10] Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
• [11] Drug Interactions Flockhart Table
• [12] Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
• [13] Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
• [14] Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
• [15] Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
• [16] Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
• [17] Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
• [18] Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
• [19] The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
• [20] Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
• [21] Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95.
• [22] Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81.
• [23] Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72.
• [24] Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8.
• [25] Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
• [26] Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
• [27] Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
• [28] Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
• [29] The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetamine in human adult and fetal liver. J Steroid Biochem Mol Biol. 1993 Jan;44(1):61-7.
• [30] Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
• [31] The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
• [32] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [33] Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid. Br J Dermatol. 1988 Nov;119(5):627-32.
• [34] Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
• [35] Discovery of a novel hybrid from finasteride and epristeride as 5alpha-reductase inhibitor. Bioorg Med Chem Lett. 2011 Jan 1;21(1):475-8.
• [36] FK143, a novel nonsteroidal inhibitor of steroid 5 alpha-reductase: (1) In vitro effects on human and animal prostatic enzymes. J Steroid Biochem Mol Biol. 1995 Apr;52(4):357-63.
• [37] Hormonal effects of turosteride, a 5 alpha-reductase inhibitor, in the rat. J Steroid Biochem Mol Biol. 1993 Nov;46(5):549-55.
• [38] Phase I and clinical pharmacology of a type I and II, 5-alpha-reductase inhibitor (LY320236) in prostate cancer: elevation of estradiol as possible... Urology. 2004 Jan;63(1):114-9.
• [39] Significant role of 5 alpha-reductase on feedback effects of androgen in rat anterior pituitary cells demonstrated with a nonsteroidal 5 alpha-redu... J Androl. 1994 Nov-Dec;15(6):521-7.
• [40] The novel drug CS-891 inhibits 5alpha-reductase activity in freshly isolated dermal papilla of human hair follicles. Eur J Dermatol. 2000 Dec;10(8):593-5.
• [41] 19-nor-10-azasteroids: a novel class of inhibitors for human steroid 5alpha-reductases 1 and 2. J Med Chem. 1997 Mar 28;40(7):1112-29.
• [42] Hydroxyperfluoroazobenzenes: novel inhibitors of enzymes of androgen biosynthesis. J Med Chem. 1990 Sep;33(9):2452-5.
• [43] Novel 5alpha-reductase inhibitors: synthesis, structure-activity studies, and pharmacokinetic profile of phenoxybenzoylphenyl acetic acids. J Med Chem. 2006 Jan 26;49(2):748-59.
• [44] Product Information. Fortovase (saquinavir) Roche Laboratories, Nutley, NJ.
• [45] Cerner Multum, Inc. "UK Summary of Product Characteristics.".
• [46] Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
• [47] Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
• [48] Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
• [49] Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
• [50] Cerner Multum, Inc. "Australian Product Information.".
• [51] Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.