General Information of Drug (ID: DMLOQ1V)

Drug Name
Tasimelteon Drug Info
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
Disease Entry ICD 11 Status REF
Insomnia 7A00-7A0Z Approved [1]
Cross-matching ID
PubChem CID
10220503
ChEBI ID
CHEBI:79042
CAS Number
CAS 609799-22-6
TTD Drug ID
DMLOQ1V
INTEDE Drug ID
DR1532
ACDINA Drug ID
D01461

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Discontinued Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ramelteon DM7IW9J Insomnia 7A00-7A0Z Approved [3]
VLB-01 DMQGV5P Epilepsy 8A60-8A68 Phase 3 [4]
2-iodo-melatonin DMSEIUP Discovery agent N.A. Investigative [5]
N-(2,3,4,9-Tetrahydro-1H-carbazol-3-yl)-acetamide DMWC70I Discovery agent N.A. Investigative [6]
5-methoxycarbonylamino-N-acetyltryptamine DMCZSP3 Discovery agent N.A. Investigative [7]
N-(3-(2-ethoxy-5-methoxyphenyl)propyl)acetamide DMLWGPC Discovery agent N.A. Investigative [8]
Beta-methylmelatonin DMKH32S Discovery agent N.A. Investigative [9]
UCM-454 DMSVJFG Discovery agent N.A. Investigative [10]
N-(3-(4-hydroxy-3-methoxyphenyl)propyl)acetamide DMILWPS Discovery agent N.A. Investigative [8]
N-(3-(5-methoxy-2-propoxyphenyl)propyl)acetamide DMHM0WI Discovery agent N.A. Investigative [8]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Melatonin DMKWFBT Depression 6A70-6A7Z Approved [11]
Ramelteon DM7IW9J Insomnia 7A00-7A0Z Approved [3]
Neu-P11 DMIQDFW Alzheimer disease 8A20 Phase 2 [12]
LY-156735 DM5IX9M Anxiety disorder 6B00-6B0Z Phase 2 [13]
Agomelatine DMXYA5K Major depressive disorder 6A70.3 Withdrawn from market [14]
Luzindole DMXRJQV Sleep-wake disorder 7A00-7B2Z Terminated [15]
S-20928 DMQDWMJ Sleep-wake disorder 7A00-7B2Z Terminated [16]
GR-133347 DMNRJA0 Anxiety disorder 6B00-6B0Z Terminated [17]
GR-131663 DMKAGLV Anxiety disorder 6B00-6B0Z Terminated [18]
SL-18.1616 DMI1WNF Insomnia 7A00-7A0Z Terminated [19]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [20]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [21]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [22]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [23]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [24]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [25]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [26]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [27]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [21]
Verapamil DMA7PEW Angina pectoris BA40 Approved [28]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [29]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [30]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [31]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [32]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [33]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [34]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [26]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [35]
Verapamil DMA7PEW Angina pectoris BA40 Approved [36]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [37]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Melatonin receptor type 1A (MTNR1A) TT0WAIE MTR1A_HUMAN Agonist [1]
Melatonin receptor type 1B (MTNR1B) TT32JK8 MTR1B_HUMAN Agonist [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [2]
Cytochrome P450 1A2 (CYP1A2) Main DME DEJGDUW CP1A2_HUMAN Substrate [2]

References

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2 Clinical assessment of drug-drug interactions of tasimelteon, a novel dual melatonin receptor agonist. J Clin Pharmacol. 2015 Sep;55(9):1004-11.
3 MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential. J Med Chem. 2014 Apr 24;57(8):3161-85.
4 Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
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7 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.
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9 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.
10 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.
11 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.
12 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).
13 Melatonin and sleep in aging population. Exp Gerontol. 2005 Dec;40(12):911-25.
14 Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders. Curr Top Med Chem. 2008;8(11):954-68.
15 Luzindole (N-0774): a novel melatonin receptor antagonist. J Pharmacol Exp Ther. 1988 Sep;246(3):902-10.
16 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.
17 US patent application no. 5,151,446, Substituted 2-amidotetralins as melatonin agonists and antagonists.
18 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.
19 US patent application no. 2005,016,4987, Melatonin combination therapy for improving sleep quality.
20 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.
21 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
22 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.
23 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
24 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.
25 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.
26 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
27 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.
28 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.
29 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.
30 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.
31 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
32 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
33 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
34 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
35 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.
36 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
37 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.