Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00665)
Name
Teriflunomide
Synonyms    Click to Show/Hide the Synonyms of This API
Teriflunomide; 163451-81-8; Flucyamide; Aubagio; 108605-62-5; A77 1726; HMR1726; HMR 1726; (Z)-2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide; HMR-1726; A 771726; A-771726; UNII-1C058IKG3B; CHEBI:68540; (Z)-2-cyano-alpha,alpha,alpha-trifluoro-3-hydroxy-p-crotonotoluidide; A 77-1726; 2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-, (2Z)-; Leflunomide Related Compound B; 1C058IKG3B; 2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)-2-butenamide; (2z)-2-Cyano-3-Hydroxy-N-[4-(Trifluoromethyl)phenyl]but-2-Enamide; (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide; Teriflunomide(Random Configuration); 2-Butenamide, 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)-; 2-Cyano-3-OH-N-(4-trifluoromethylphenyl)croton amide; 2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-; (Z)-2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide.; MFCD00910058; RS 61980; Teriflunomide [USAN:INN]; teriflunomida; teriflunomidum; 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-2-butenamide; Malononitrilamide; N-(4-Trifluoromethylphenyl)-2-cyano-2-hydroxycrotonamide; Aubagio (TN); 1185240-22-5; SU-0020; Leflunomide Impurity B; Teriflunomide (USAN); RS-61980; Leflunomide EP Impurity B; (2Z)-2-[hydroxy-[4-(trifluoromethyl)anilino]methylidene]-3-oxobutanenitrile; A 1726; SCHEMBL22661; Teriflunomide(A-771726); Teriflunomide, A77 1726; A77-1726; GTPL6844; DTXSID80893457; Leflunomide related compound b rs; BDBM50018011; NSC766118; ZINC13512456; AKOS015994773; CCG-267145; DB08880; LE-0275; NSC-766118; SB16822; NCGC00263218-07; NCGC00263218-13; AC-26446; SW219377-1; Leflunomide-d4 Metabolite (Teriflunomide-d4); D10172; AB01565775_02; A801897; J-010046; Q3077133; N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide; N-[4-(Trifluoromethyl)phenyl]-2-cyano-3-hydroxycrotonamide; (Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide; 163451-81-8 (Z Isomer) , 108605-62-5 (E/Z Mixture); 2-Butenamide, 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)-, (Z)-; A 77-1726;A771726;HMR1726;CAS# 108605-62-5; (2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide (Teriflunomide); 2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide (E/Z)-mixture; Leflunomide Related Compound B, United States Pharmacopeia (USP) Reference Standard; (2Z)-3-oxidanylidene-2-[oxidanyl-[[4-(trifluoromethyl)phenyl]amino]methylidene]butanenitrile; Teriflunomide; Leflunomide USP RC B; Cyano Keto leflunomide impurity; N-(4-Trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide; 2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-beuteamide
Clinical Status
Approved
Disease Indication Multiple sclerosis ICD-11: 8A40 [1]
PubChem CID
54684141
Formula
C12H9F3N2O2
Canonical SMILES
C/C(=C(\\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O
InChI
1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
InChIKey
UTNUDOFZCWSZMS-YFHOEESVSA-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=54684141"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 270.21 Topological Polar Surface Area 73.1
XlogP 3.3 Complexity 426
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Teriflunomide 7 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 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; Fd&c blue no. 2; Magnesium stearate; Ferric oxide yellow; Talc; Titanium dioxide; Hydroxypropyl cellulose (1200000 mw); Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Sodium starch glycolate type a corn; Starch, corn
                   Dosage Form Oral Tablet
                   Company Genzyme Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Teriflunomide 14 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 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; Fd&c blue no. 2; Magnesium stearate; Talc; Titanium dioxide; Hydroxypropyl cellulose (1200000 mw); Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Sodium starch glycolate type a corn; Starch, corn
                   Dosage Form Oral Tablet
                   Company Genzyme Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved teriflunomide 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 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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