Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00221)
Name
Dutasteride
Synonyms    Click to Show/Hide the Synonyms of This API
Dutasteride; 164656-23-9; Avodart; GG-745; GI 198745; GI-198745; UNII-O0J6XJN02I; C27H30F6N2O2; O0J6XJN02I; (5alpha,17beta)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide; alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide; CHEMBL1200969; Avolve; CHEBI:521033; Dutasteride, 99%; (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; (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(2,5-Bis(trifluoromethyl)phenyl)-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; (1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide; GG 745; Duagen; 1H-Indeno[5,4-f]quinoline-7-carboxamide, N-[2,5-bis(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-; Avodart (TN); GI198745; Avidart; Dutasteride [USAN:INN:BAN]; NCGC00164571-01; 1H-Indeno(5,4-f)quinoline-7-carboxamide, N-(2,5-bis(trifluoromethyl)phenyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-; GI-198745X; SCHEMBL5903; DSSTox_CID_26452; DSSTox_RID_81626; DSSTox_GSID_46452; Dutasteride (JAN/USP/INN); GTPL7457; DTXSID8046452; Dutasteride, >=98% (HPLC); AOB5568; BCPP000248; BCP02344; EX-A1952; ZINC3932831; Tox21_112199; BDBM50340481; MFCD00937869; NSC740477; AKOS015920136; AKOS015924431; BCP9000630; CCG-269904; CS-1542; DB01126; GS-3565; MCULE-1602474627; NSC-740477; N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide; BR-72895; HY-13613; CAS-164656-23-9; B-2151; D03820; J10036; AB01274774-01; AB01274774_02; 656D239; Q424760; Q-201052; BRD-K30373883-001-02-8; Z1563146168; Dutasteride, European Pharmacopoeia (EP) Reference Standard; Dutasteride, United States Pharmacopeia (USP) Reference Standard; Dutasteride for system suitability, European Pharmacopoeia (EP) Reference Standard; (5.alpha.,5 bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide;dutasteride;Avodart;; (5alpha,17beta)-N-{2,5-bis(trifluoromethyl)-phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide
Clinical Status
Approved
Disease Indication Prostatic hyperplasia ICD-11: GA90 [1]
PubChem CID
6918296
Formula
C27H30F6N2O2
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
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6918296"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 528.5 Topological Polar Surface Area 58.2
XlogP 5.4 Complexity 964
Heavy Atom Count 37 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Full List of Drug Formulations (DFMs) Containing This API
          Dutasteride 0.5 mg capsule Click to Show/Hide the Full List of Formulation(s):        16 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Butylated hydroxytoluene; Fd&c blue no. 1; Ammonia; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Titanium dioxide; Medium-chain triglycerides; Polysorbate 80; Caprylic/capric mono/diglycerides; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [5]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous citric acid; Glycine; Butylated hydroxytoluene; Isopropyl alcohol; Ferric oxide yellow; Glycerin; Titanium dioxide; Water; Medium-chain triglycerides; Caprylic/capric mono/diglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company Strides Shasun
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [7]
Aminoethanoic acid DIG Info Glycine type-1 transporter (IC50 = 31600 nM) [8]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [9]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Fd&c red no. 40; Caprylic/capric acid; Isopropyl alcohol; Ferric oxide yellow; Glycerin; Propylene glycol; Titanium dioxide; Water; Gelatin; Hypromellose 2208 (100 mpa.s)
                   Dosage Form Oral Capsule
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [5]
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Caprylic acid DIG Info GPCR84 receptor (Ki = 19600 nM) [10]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [2]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [9]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Butyl alcohol; Isopropyl alcohol; Ammonia; Ferric oxide red; Ferric oxide yellow; Glycerin; Propylene glycol; Titanium dioxide; Medium-chain triglycerides; Caprylic/capric mono/diglycerides; Dimethicone; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Epic Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [9]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ammonia; Ferric oxide yellow; Ferrosoferric oxide; Glycerin; Propylene glycol; Talc; Titanium dioxide; Lecithin, soybean; Medium-chain triglycerides; Caprylic/capric mono/diglycerides; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [4]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ammonia; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Glycerin; Propylene glycol; Titanium dioxide; Lecithin, soybean; Medium-chain triglycerides; Caprylic/capric mono/diglycerides; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Breckenridge Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [4]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ferric oxide yellow; Ferrosoferric oxide; Glycerin; Propylene glycol; Titanium dioxide; Lecithin, soybean; Medium-chain triglycerides; Caprylic/capric mono/diglycerides; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Actavis Pharma; Proficient Rx
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [4]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
             Drug Formulation 8 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Isopropyl alcohol; Ferric oxide yellow; Ferrosoferric oxide; Glycerin; Propylene glycol; Titanium dioxide; Water; Caprylic/capric mono/diglycerides; Gelatin; Hypromelloses
                   Dosage Form Oral Capsule
                   Company Impax Generics
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [9]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
             Drug Formulation 9 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Capric acid; Sorbitol; Ferric oxide yellow; Glycerin; Titanium dioxide; Water; Gelatin
                   Dosage Form Oral Capsule
                   Company Marksans Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Caprylic acid DIG Info GPCR84 receptor (Ki = 19600 nM) [10]
             Drug Formulation 10 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ammonia; Ferric oxide red; Ferric oxide yellow; Glycerin; Propylene glycol; Titanium dioxide; Caprylic/capric mono/diglycerides; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Apotex; Golden State Medical Supply
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
             Drug Formulation 11 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ferric oxide yellow; Ferrosoferric oxide; Glycerin; Propylene glycol; Titanium dioxide; Caprylic/capric mono/diglycerides; Gelatin; Hypromelloses
                   Dosage Form Oral Capsule
                   Company AvPAK; Camber Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
             Drug Formulation 12 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Glyceryl caprylate/caprate; Ferric oxide yellow; Glycerin; Titanium dioxide; Water; Gelatin
                   Dosage Form Oral Capsule
                   Company Amneal Pharmaceuticals; AvKARE
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
             Drug Formulation 13 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ferric oxide yellow; Ferrosoferric oxide; Glycerin; Titanium dioxide; Caprylic/capric mono/diglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company Rising Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
             Drug Formulation 14 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ferric oxide yellow; Glycerin; Titanium dioxide; Caprylic/capric mono/diglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company Intergel Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
             Drug Formulation 15 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ferric oxide yellow; Glycerin; Caprylic/capric mono/diglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company Preferred Pharamaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
             Drug Formulation 16 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Ferric oxide yellow; Glycerin; Caprylic/capric mono/diglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company A-S Medication Solutions; Avera McKennan Hospital; GlaxoSmithKline; Lake Eire Medical & Surgical Supply DBA Quality Care Products; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [3]
References
1 FDA label for approved dutasteride from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
5 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
6 Interactions between human multidrug resistance related protein (MRP2; ABCC2) and excipients commonly used in self-emulsifying drug delivery systems (SEDDS). Int J Pharm. 2013 Apr 15;447(1-2):192-8.
7 PubChem BioAssay data set.
8 Novel GlyT1 inhibitor chemotypes by scaffold hopping. Part 1: development of a potent and CNS penetrant [3.1.0]-based lead. Bioorg Med Chem Lett. 2014 Feb 15; 24(4):1067-70.
9 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
10 An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights. J Med Chem. 2020 Mar 12; 63(5):2391-2410.

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