Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00288)
Name
Flutamide
Synonyms    Click to Show/Hide the Synonyms of This API
flutamide; 13311-84-7; Eulexin; Niftolide; Niftholide; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide; niftolid; Drogenil; Sch 13521; Flutamin; Cebatrol, veterinary; Flutamida; Flutamidum; Sch-13521; 4'-Nitro-3'-trifluoromethylisobutyranilide; N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)ISOBUTYRAMIDE; Propanamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-; 2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide; SCH13521; MFCD00072009; NSC 215876; Flutamide (Eulexin); alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide; UNII-76W6J0943E; CHEMBL806; 4-Nitro-3-(trifluoromethyl)isobutyranilide; CHEBI:5132; Propanamide, 2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)-; 76W6J0943E; NSC-215876; NCGC00015452-09; Eulexine; Chimax; 4'-Nitro-3'-trifluoromethylisobutyramilide; CAS-13311-84-7; Ham's F-12 medium; Flutamidum [INN-Latin]; DSSTox_CID_11121; DSSTox_RID_78899; DSSTox_GSID_32004; Flutamida [INN-Spanish]; Flutamide USP25; Prostandril; 37209-54-4; SMR000058187; Eulexin (TN); CCRIS 7246; m-Propionotoluidide,.alpha.,.alpha.-trifluoro-; SR-01000075888; N-[4-Nitro-3-(trifluoromethyl)phenyl]isobutyramide; EINECS 236-341-9; BRN 2157663; N1-[4-nitro-3-(trifluoromethyl)phenyl]-2-methylpropanamide; .alpha.,.alpha.-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide; m-Propionotoluidide,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-; 4'-Nitro-3'-(trifluoromethyl)isobutyranilide; Flutamide [USAN:USP:INN:BAN]; Flutamide,(S); Prestwick_228; NK-601; ACMC-20hidt; PubChem13536; Spectrum_001210; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide; CPD000058187; Prestwick0_000180; Prestwick1_000180; Prestwick2_000180; Prestwick3_000180; Spectrum2_001201; Spectrum3_001421; Spectrum4_000829; Spectrum5_001450; Lopac-F-9397; Flutamide (pubertal study); F 9397; SCHEMBL3934; Lopac0_000557; BSPBio_000079; BSPBio_003122; KBioGR_001377; KBioSS_001690; MLS000069634; MLS001065596; MLS002548892; DivK1c_000459; SPECTRUM1500995; SPBio_000982; SPBio_002000; Flutamide (JP17/USP/INN); BPBio1_000087; GTPL6943; DTXSID7032004; SCHEMBL12932289; HMS501G21; KBio1_000459; KBio2_001690; KBio2_004258; KBio2_006826; KBio3_002342; NINDS_000459; HMS1568D21; HMS1921O16; HMS2090I18; HMS2092O14; HMS2095D21; HMS2230P19; HMS3259I03; HMS3261P15; HMS3373C12; HMS3655G22; HMS3712D21; Pharmakon1600-01500995; BCP23006; HY-B0022; ZINC3812944; Tox21_110154; Tox21_202169; Tox21_300536; Tox21_500557; BDBM50131270; CCG-39105; m-Propionotoluidide, 2-methyl-4'-nitro-alpha,alpha,alpha-triflouro-; NSC147834; NSC215876; NSC757817; SBB006930; AKOS001025465; AKOS025243203; m-Propionotoluidide, .alpha.,.alpha.,.alpha.-trifluoro-2-methyl-4'-nitro-; Tox21_110154_1; AB02835; DB00499; KS-5091; LP00557; MCULE-7498839065; NC00451; NSC-147834; NSC-757817; SDCCGSBI-0050540.P004; IDI1_000459; NCGC00015452-01; NCGC00015452-02; NCGC00015452-03; NCGC00015452-04; NCGC00015452-05; NCGC00015452-06; NCGC00015452-07; NCGC00015452-08; NCGC00015452-10; NCGC00015452-11; NCGC00015452-12; NCGC00015452-13; NCGC00015452-14; NCGC00015452-15; NCGC00015452-16; NCGC00015452-19; NCGC00015452-20; NCGC00015452-32; NCGC00091460-01; NCGC00091460-02; NCGC00091460-03; NCGC00091460-04; NCGC00091460-05; NCGC00091460-06; NCGC00091460-07; NCGC00091460-08; NCGC00091460-09; NCGC00254495-01; NCGC00259718-01; NCGC00261242-01; AC-24192; AK499646; ST058409; SY036411; SBI-0050540.P003; AB0005010; DB-042163; 3'-Trifluoromethyl-4'-Nitro-Isobutyranilide; AB00052188; EU-0100557; FT-0626493; FT-0668764; SW196536-4; 4''-nitro-3''-trifluoromethylisobutyranilide; C07653; D00586; J10037; K-4175; AB00052188-09; AB00052188_10; AB00052188_11; 311F847; A806562; Q418669; Q-201131; SR-01000075888-1; SR-01000075888-6; SR-01000075888-7; SR-01000075888-9; BRD-K28307902-001-05-0; Flutamide, certified reference material, TraceCERT(R); Z56755651; a,a,a-Trifluoro-2-methyl-4'-nitro- m-propionotoluidide; Flutamide, European Pharmacopoeia (EP) Reference Standard; 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide #; Flutamide, United States Pharmacopeia (USP) Reference Standard; alpha,alpha,alpha-trifluoro-2-methyl-4''-nitro-m-propionotoluidide; .alpha.,.alpha.,.alpha.-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide; m-Propionotoluidide, 2-methyl-4'-nitro-.alpha.,.alpha.,.alpha.-trifluoro-; m-Propionotoluidide, alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro- (8CI); Flutamide for system suitability, European Pharmacopoeia (EP) Reference Standard
Clinical Status
Approved
Disease Indication Prostate cancer ICD-11: 2C82 [1]
PubChem CID
3397
Formula
C11H11F3N2O3
Canonical SMILES
CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
InChI
1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
InChIKey
MKXKFYHWDHIYRV-UHFFFAOYSA-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=3397"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 276.21 Topological Polar Surface Area 74.9
XlogP 3.3 Complexity 352
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Flutamide 125 mg capsule Click to Show/Hide the Full List of Formulation(s):          5 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
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Butyl alcohol; Fd&c blue no. 1; Fd&c blue no. 2; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Povidone; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Actavis Pharma
                   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) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Butyl alcohol; Fd&c blue no. 1; Fd&c blue no. 2; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Titanium dioxide; Silicon dioxide; Gelatin, unspecified; Povidone, unspecified; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Golden State Medical Supply
                   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) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 2; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Titanium dioxide; Aluminum oxide; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Cipla
                   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) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             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
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 2; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Titanium dioxide; Gelatin, unspecified; Starch, corn
                   Dosage Form Oral Capsule
                   Company Teva Pharmaceuticals
                   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) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose; Sodium lauryl sulfate; Magnesium stearate; Povidone; Corn starch
                   Dosage Form Oral Capsule
                   Company Schering Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
References
1 FDA label for approved flutamide from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 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.
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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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