Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01461)
Name
Tasimelteon
Synonyms    Click to Show/Hide the Synonyms of This API
Tasimelteon; 609799-22-6; Hetlioz; VEC-162; BMS-214778; VEC 162; BMS 214778; UNII-SHS4PU80D9; SHS4PU80D9; CHEBI:79042; BMS214778; N-(((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methyl)propionamide; N-{[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl}propanamide; Tasimelteon [USAN:INN]; tasimelteonum; N-(((1R,2R)-2-(2,3-Dihydro-1-benzofuran-4-yl)cyclopropyl)methyl)propanamide; N-([(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl)propanamide; N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide; Hetlioz (TN); Tasimelteon (USAN/INN); GTPL7393; SCHEMBL3505912; CHEMBL2103822; Tasimelteon, >=98% (HPLC); AMY6925; DTXSID70209826; HMS3885L17; ACT06729; BCP07180; EX-A2729; ZINC4392649; MFCD09033789; s4281; AKOS025149360; AC-6143; CCG-266915; CS-5512; DB09071; SB16782; BMS-214,778; NCGC00522560-01; AS-35291; HY-14803; X5820; J3.640.465E; D09388; 799T226; Q7687250; N-((2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)propanamide; (trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl) cyclopropyl]methyl]propanamide; (trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl]methyl]propanamide; (-)-(trans)-N-[[2-(2,3-Dihydrobenzofuran-4-yl)cycloprop-1-yl] methyl]propanamide; Propanamide, N-(((1R,2R)-2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)-
Clinical Status
Approved
PubChem CID
10220503
Formula
C15H19NO2
Canonical SMILES
CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2
InChI
1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1
InChIKey
PTOIAAWZLUQTIO-GXFFZTMASA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 245.32 Topological Polar Surface Area 38.3
XlogP 2.2 Complexity 318
Heavy Atom Count 18 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Tasimelteon 20mg capsule 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
Colloidal Silicon Dioxide; Croscarmellose Sodium; Lactose Anhydrous; Magnesium Stearate; Microcrystalline Cellulose; Fd&C Blue 1; Fd&C Red 3; Fd&C Yellow 6; Gelatin; Titanium Dioxide
                   Dosage Form Capsule
                   Company Vanda Pharms
                   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) [1]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [1]
Erythrosine sodium anhydrous DIG Info Multidrug resistance protein 3 (IC50 = 133000 nM) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
          Tasimelteon 4mg/ml suspension 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
Ascorbic Acid; Cherry Flavor; Mannitol; Microcrystalline Cellulose/Carboxymethylcellulose Sodium; Polysorbate 80; Sodium Benzoate; Sodium Chloride; Sucrose; Sucralose; Water
                   Dosage Form Suspension
                   Company Vanda Pharms
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sucralose DIG Info Carbonic anhydrase II (Ki = 300 nM) [5]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [6]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [7]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [8]
Ascorbic acid DIG Info Albendazole monooxygenase (IC50 = 4.1 mg.mL-1) [9]
References
1 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.
2 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov; 136(1):216-41.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
6 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
7 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
8 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
9 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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