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

General Information of Drug (ID: DR0472)
Drug Name
Dexmedetomidine hydrochloride
Synonyms
Dexmedetomidine (hydrochloride); Dexmedetomidine HCL; Dexmedetomidine HCl (Precedex); Dexmedetomidine hydrochloride; Dexmedetomidine hydrochloride [USAN]; UNII-1018WH7F9I; (S)-4-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole hydrochloride; (S)-5-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole hydrochloride; 1018WH7F9I; 145108-58-3; 4-((S)-alpha,2,3-trimethylbenzyl)imidazole monohydrochloride; 4-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole hydrochloride; CHEBI:31472
Indication Tension headache [ICD11: 8A81] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 236.74 Topological Polar Surface Area 28.7
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
6918081
ChEBI ID
CHEBI:31472
CAS Number
145108-58-3
TTD Drug ID
D0U3DU
Formula
C13H17ClN2
Canonical SMILES
CC1=C(C(=CC=C1)C(C)C2=CN=CN2)C.Cl
InChI
1S/C13H16N2.ClH/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13;/h4-8,11H,1-3H3,(H,14,15);1H/t11-;/m0./s1
InChIKey
VPNGEIHDPSLNMU-MERQFXBCSA-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
Dexmedetomidine N-glucuronidation DM000815 N. A. Conjugation - Glucuronidation 1 [5]
MPV-1305 DM000812 N. A. Oxidation - Hydroxylation 1 [6]
MPV-1709 DM000808 N. A. Conjugation - N-Methylation 1 [6]
3-hydroxy N-methyl-dexmedetomidine DM000809 N. A. Oxidation - Hydroxylation 2 [7]
Hydroxydexmedetomidine-O-glucuronidation DM000813 N. A. Conjugation - Glucuronidation 2 [6]
MPV-1036 DM000814 N. A. Unclear 2 [6]
3-carboxy N-methyl-dexmedetomidine DM000811 N. A. Unclear 3 [7]
Dexmedetomidine-N-methyl O-glucuronide DM000810 N. A. Conjugation - Glucuronidation 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000802 Dexmedetomidine hydrochloride MPV-1709 Conjugation - N-Methylation Unclear [6]
MR000803 Dexmedetomidine hydrochloride MPV-1305 Oxidation - Hydroxylation CYP2A6 [6]
MR000804 Dexmedetomidine hydrochloride Dexmedetomidine N-glucuronidation Conjugation - Glucuronidation UGT1A4 ... [5]
MR000800 MPV-1305 Hydroxydexmedetomidine-O-glucuronidation Conjugation - Glucuronidation Unclear [6]
MR000801 MPV-1305 MPV-1036 Unclear Unclear [6]
MR000797 MPV-1709 3-hydroxy N-methyl-dexmedetomidine Oxidation - Hydroxylation Unclear [7]
MR000798 3-hydroxy N-methyl-dexmedetomidine Dexmedetomidine-N-methyl O-glucuronide Conjugation - Glucuronidation Unclear [7]
MR000799 3-hydroxy N-methyl-dexmedetomidine 3-carboxy N-methyl-dexmedetomidine Unclear Unclear [7]
⏷ Show the Full List of 8 MR(s)
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 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Homo sapiens
UDB10_HUMAN
2.4.1.17
[5]
References
1 Dexmedetomidine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Predominant role of peripheral catecholamines in the stress-induced modulation of CYP1A2 inducibility by benzo(alpha)pyrene. Basic Clin Pharmacol Toxicol. 2008 Jan;102(1):35-44.
3 Impact of CYP2A6 gene polymorphism on the pharmacokinetics of dexmedetomidine for premedication. Expert Rev Clin Pharmacol. 2018 Sep;11(9):917-922.
4 Metabolic stability and determination of cytochrome P450 isoenzymes' contribution to the metabolism of medetomidine in dog liver microsomes. Biomed Chromatogr. 2010 Aug;24(8):868-77.
5 Large inter-individual variability in pharmacokinetics of dexmedetomidine and its two major N-glucuronides in adult intensive care unit patients J Pharm Biomed Anal. 2019 Oct 25;175:112777. doi: 10.1016/j.jpba.2019.07.025.
6 Analytical method development for the simultaneous quantitation of dexmedetomidine and three potential metabolites in plasma J Chromatogr A. 1997 Feb 21;762(1-2):281-91. doi: 10.1016/s0021-9673(96)00965-x.
7 LABEL:EXMEDETOMIDINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE injection

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