Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1532)
Drug Name
Tasimelteon
Synonyms
Tasimelteon; Tasimelteon (USAN/INN); Tasimelteon [USAN:INN]; VEC 162; VEC-162; tasimelteonum; 609799-22-6; BMS 214778; BMS-214778; CHEBI:79042; Hetlioz; Hetlioz (TN); SCHEMBL3505912; SHS4PU80D9; GTPL7393; 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; N-{[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl}propanamide; UNII-SHS4PU80D9
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 245.32 Topological Polar Surface Area 38.3
Heavy Atom Count 18 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
10220503
PubChem SID
15221060 ; 22609327 ; 40334994 ; 46387835 ; 78704256 ; 92722464 ; 96026068 ; 126627315 ; 126662442 ; 128966262 ; 135253193 ; 137132834 ; 137788131 ; 141198068 ; 160676375 ; 164777429 ; 165238001 ; 178103965 ; 180371725 ; 198968673 ; 198994004 ; 223444257 ; 223675953 ; 225045086 ; 229516194 ; 241124240 ; 251971356 ; 252552922 ; 252671867
ChEBI ID
CHEBI:79042
CAS Number
609799-22-6
TTD Drug ID
D0Q5MQ
Formula
C15H19NO2
Canonical SMILES
CCC(=O)NCC1CC1C2=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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Inosine DM003100
135398641
Oxidation - Hydroxylation 1 [3]
Tasimelteon metabolite M13 DM000452
118287331
Oxidation - Hydroxylation 1 [3]
Tasimelteon metabolite M14 DM000455
156596491
Oxidation - Hydroxylation 1 [3]
Tasimelteon metabolite M11 DM000454
72202006
Unclear 2 [3]
Tasimelteon metabolite M9 DM000453
72188561
Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002340 Tasimelteon Tasimelteon metabolite M13 Oxidation - Hydroxylation CYP1A2 ... [3]
MR002341 Tasimelteon Tasimelteon metabolite M14 Oxidation - Hydroxylation CYP3A4 [3]
MR002342 Tasimelteon Inosine Oxidation - Hydroxylation CYP1A2 ... [3]
MR002338 Tasimelteon metabolite M13 Tasimelteon metabolite M9 Unclear CYP1A2 ... [3]
MR002339 Tasimelteon metabolite M13 Tasimelteon metabolite M11 Unclear CYP1A2 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
⏷ Show the Full List of 6  DME(s)
References
1 Tasimelteon was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical assessment of drug-drug interactions of tasimelteon, a novel dual melatonin receptor agonist J Clin Pharmacol. 2015 Sep;55(9):1004-11. doi: 10.1002/jcph.507.
3 Clinical assessment of drug-drug interactions of tasimelteon, a novel dual melatonin receptor agonist. J Clin Pharmacol. 2015 Sep;55(9):1004-11.

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