Details of the Drug
General Information of Drug (ID: DMLOQ1V)
Drug Name |
Tasimelteon
|
|||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Synonyms |
Tasimelteon; 609799-22-6; Hetlioz; VEC-162; BMS-214778; VEC 162; UNII-SHS4PU80D9; BMS 214778; SHS4PU80D9; CHEBI:79042; 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); SCHEMBL3505912; GTPL7393
|
|||||||||||||||||||
Indication |
|
|||||||||||||||||||
Drug Type |
Small molecular drug
|
|||||||||||||||||||
Structure | ||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 245.32 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 2.2 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 4 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 1 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 2 | |||||||||||||||||||
ADMET Property |
|
|||||||||||||||||||
Chemical Identifiers |
|
|||||||||||||||||||
Cross-matching ID | ||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
|
|||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Drug-Metabolizing Enzyme (DME) |
|
|||||||||||||||||||||||||||||||
Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Disease Different from Tasimelteon (Comorbidity)
|
Drug Inactive Ingredient(s) (DIG) and Formulation(s) 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: 7393). | ||||
---|---|---|---|---|---|
2 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | ||||
3 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
4 | 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. | ||||
5 | An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9. | ||||
6 | Clinical assessment of drug-drug interactions of tasimelteon, a novel dual melatonin receptor agonist. J Clin Pharmacol. 2015 Sep;55(9):1004-11. | ||||
7 | 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. | ||||
8 | Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. | ||||
9 | 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. | ||||
10 | Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. | ||||
11 | 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. | ||||
12 | 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. | ||||
13 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
14 | 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. | ||||
15 | 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. | ||||
16 | Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63. | ||||
17 | Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8. | ||||
18 | Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. | ||||
19 | Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65. | ||||
20 | PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. | ||||
21 | The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184. | ||||
22 | The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46. | ||||
23 | Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7. | ||||
24 | Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509. | ||||
25 | MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential. J Med Chem. 2014 Apr 24;57(8):3161-85. | ||||
26 | Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41. | ||||
27 | Synthesis of nitroindole derivatives with high affinity and selectivity for melatoninergic binding sites MT(3). J Med Chem. 2002 Apr 25;45(9):1853-9. | ||||
28 | Mapping the melatonin receptor. 2. synthesis and biological activity of indole derived melatonin analogues with restricted conformations of the C-3 amidoethane side chain, Bioorg. Med. Chem. Lett. 4(13):1559-1564 (1994). | ||||
29 | Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3. Bioorg Med Chem. 2008 May 1;16(9):4954-62. | ||||
30 | Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands. Bioorg Med Chem Lett. 2010 Apr 15;20(8):2582-5. | ||||
31 | Mapping the melatonin receptor. 7. Subtype selective ligands based on beta-substituted N-acyl-5-methoxytryptamines and beta-substituted N-acyl-5-me... J Med Chem. 2006 Jun 15;49(12):3509-19. | ||||
32 | 2-[(2,3-dihydro-1H-indol-1-yl)methyl]melatonin analogues: a novel class of MT2-selective melatonin receptor antagonists. J Med Chem. 2009 Feb 12;52(3):826-33. | ||||
33 | The human MT1 melatonin receptor stimulates cAMP production in the human neuroblastoma cell line SH-SY5Y cells via a calcium-calmodulin signal transduction pathway. J Neuroendocrinol. 2005 Mar;17(3):170-8. | ||||
34 | 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. (Target id: 288). | ||||
35 | Melatonin and sleep in aging population. Exp Gerontol. 2005 Dec;40(12):911-25. | ||||
36 | Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders. Curr Top Med Chem. 2008;8(11):954-68. | ||||
37 | Luzindole (N-0774): a novel melatonin receptor antagonist. J Pharmacol Exp Ther. 1988 Sep;246(3):902-10. | ||||
38 | Effects of two melatonin analogues, S-20098 and S-20928, on melatonin receptors in the pars tuberalis of the rat. J Pineal Res. 1998 Oct;25(3):172-6. | ||||
39 | US patent application no. 5,151,446, Substituted 2-amidotetralins as melatonin agonists and antagonists. | ||||
40 | Novel non-indolic melatonin receptor agonists differentially entrain endogenous melatonin rhythm and increase its amplitude. Eur J Pharmacol. 1999 Oct 15;382(3):157-66. | ||||
41 | US patent application no. 2005,016,4987, Melatonin combination therapy for improving sleep quality. | ||||
42 | Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD. | ||||
43 | US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.". | ||||
44 | Patel S, Robinson R, Burk M "Hypertensive crisis associated with St. John's Wort." Am J Med 112 (2002): 507-8. [PMID: 11959071] | ||||
45 | Cerner Multum, Inc. "Australian Product Information.". | ||||
46 | Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA. | ||||
47 | Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN. | ||||
48 | Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ. | ||||
49 | Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA. | ||||
50 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
51 | Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA. | ||||