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

General Information of Drug (ID: DR1391)
Drug Name
Ramelteon
Synonyms
Ramelteon; Ramelteon [USAN]; Rozerem; TAK-375; (-)-N-(2-(((8S)-1,6,7,8-Tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)propanamide; (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide; (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl)propionamide; (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide; 196597-26-9; 901AS54I69; CHEMBL1218; N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide; UNII-901AS54I69
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 259.339 Topological Polar Surface Area 38.3
Heavy Atom Count 19 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
208902
PubChem SID
9368722 ; 12015157 ; 14823708 ; 14847999 ; 17396858 ; 26612945 ; 30413545 ; 46505923 ; 47810466 ; 50070191 ; 50070903 ; 50810551 ; 57399556 ; 71825382 ; 81065549 ; 85789647 ; 90342558 ; 92124722 ; 92307942 ; 92721412 ; 99437057 ; 103370203 ; 103838767 ; 104011788 ; 113442055 ; 117539034 ; 124757124 ; 124772078 ; 125163928 ; 126592922 ; 126627642 ; 126651547 ; 126667057 ; 129814520 ; 134337398 ; 135184679 ; 135651228 ; 136949090 ; 137005126 ; 142796849 ; 143496454 ; 152035160 ; 152164855 ; 152237728 ; 152258949 ; 160647794 ; 160964318 ; 162011666 ; 162184404 ; 163122411
ChEBI ID
CHEBI:109549
CAS Number
196597-26-9
TTD Drug ID
D0U0KW
Formula
C16H21NO2
Canonical SMILES
CCC(=O)NCCC1CCC2=C1C3=C(C=C2)OCC3
InChI
1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1
InChIKey
YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [4]
⏷ Show the Full List of 17  DME(s)
References
1 Ramelteon was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91.
3 Pharmacotherapy of insomnia with ramelteon: safety, efficacy and clinical applications. J Cent Nerv Syst Dis. 2011 Apr 12;3:51-65.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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