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

General Information of Drug (ID: DR5393)
Drug Name
Dimenhydrinate
Synonyms
Gravamin (TN); Gravol (TN); Vertirosan (TN); Dimenhydrinate (JP15/USP/INN); 2-(diphenylmethoxy)-N,N-dimethylethanaminium 8-chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ide; 2-benzhydryloxyethyl(dimethyl)azanium; 8-chloro-1,3-dimethyl-2-oxopurin-6-olate; 8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione-2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1)
Indication Nausea [ICD11: MD90] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 470 Topological Polar Surface Area 81.8
Heavy Atom Count 33 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
10660
ChEBI ID
CHEBI:94848
CAS Number
523-87-5
TTD Drug ID
D0U8UV
Formula
C24H28ClN5O3
Canonical SMILES
CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChI=1S/C17H21NO.C7H7ClN4O2/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h3-12,17H,13-14H2,1-2H3;1-2H3,(H,9,10)
InChIKey
NFLLKCVHYJRNRH-UHFFFAOYSA-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
8-chlorotheophylline DM018827 N. A. Unclear - Unclear 1 [2]
Diphenhydramine DM014858
3100
Unclear - Unclear 1 [2]
Diphenyl-methoxy-acetic acid DM018828 N. A. Unclear - Unclear 1 [3]
Diphenyl-methoxy-ethylamine DM018829 N. A. Unclear - Unclear 1 [3]
Diphenyl-methoxy-N-methyl-amine DM018830 N. A. Unclear - Unclear 1 [3]
Diphenhydramine N-glucuronide DM000109
178420
Unclear - Unclear 2 [4]
N-desmethyldiphenhydramine DM000105
40791
Unclear - Unclear 2 [4]
N,N-didesmethyldiphenhydramine DM000106
36060
Unclear - Unclear 3 [4]
Diphenylmethoxyacetic acid DM000107
597513
Unclear - Unclear 4 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR011192 Dimenhydrinate Diphenhydramine Unclear - Unclear Unclear [2]
MR011197 Dimenhydrinate 8-chlorotheophylline Unclear - Unclear Unclear [2]
MR011198 Dimenhydrinate Diphenyl-methoxy-acetic acid Unclear - Unclear Unclear [3]
MR011199 Dimenhydrinate Diphenyl-methoxy-ethylamine Unclear - Unclear Unclear [3]
MR011200 Dimenhydrinate Diphenyl-methoxy-N-methyl-amine Unclear - Unclear Unclear [3]
MR011193 Diphenhydramine N-Desmethyldiphenhydramine Unclear - Unclear CYP2C9 ... [4]
MR011196 Diphenhydramine Diphenhydramine N-glucuronide Unclear - Unclear UGT [4]
MR011194 N-Desmethyldiphenhydramine N,N-Didesmethyldiphenhydramine Unclear - Unclear Unclear [4]
MR011195 N,N-Didesmethyldiphenhydramine Diphenylmethoxyacetic acid Unclear - Unclear Unclear [4]
⏷ Show the Full List of 9 MR(s)
References
1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040519.
2 Pubmed:Dimenhydrinate
3 Serum levels of dimenhydrinate. Determination by HPLC with UV detection after intake of dimenhydrinate in a coated chewing gum dragee
4 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.

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