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

General Information of Drug (ID: DR0265)
Drug Name
Cannabidiol
Synonyms
Cannabidiol; delta1(2)-trans-Cannabidiol; Epidiolex; QHMBSVQNZZTUGM-ZWKOTPCHSA-N; (-)-CBD; (-)-Cannabidiol; (-)-trans-2-p-Mentha-1,8-dien-3-yl-5-pentylresorcinol; (-)-trans-Cannabidiol; 1,3-Benzenediol, 2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, (1R-trans)-; 13956-29-1; 19GBJ60SN5; 2-((1R,6R)-6-Isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol; 2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol; CBD; CHEBI:69478; CHEMBL190461; GWP42003-P; UNII-19GBJ60SN5
Indication Lennox-Gastaut syndrome [ICD11: 8A62] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 314.5 Topological Polar Surface Area 40.5
Heavy Atom Count 23 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
644019
PubChem SID
841235 ; 8707245 ; 12012585 ; 14825860 ; 14899058 ; 24892861 ; 43765781 ; 57309735 ; 57408178 ; 57654032 ; 80649036 ; 103460177 ; 104014242 ; 104152845 ; 109827355 ; 113635231 ; 134990571 ; 135697550 ; 136213730 ; 142472550 ; 160711726 ; 162224688 ; 178100971 ; 198983043 ; 224092533 ; 226491388 ; 242059005 ; 250138861 ; 252159978 ; 252415453
ChEBI ID
CHEBI:69478;
CAS Number
145514-04-1
TTD Drug ID
D0O1UZ
Formula
C21H30O2
Canonical SMILES
CCCCCC1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O
InChI
1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1
InChIKey
QHMBSVQNZZTUGM-ZWKOTPCHSA-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
1''-Hydroxycannabidiol DM020027
121596213
Oxidation - Hydroxylation 1 [3]
2''-Hydroxycannabidiol DM020028
121596214
Oxidation - Hydroxylation 1 [3]
3''-Hydroxycannabidiol DM020029
121596215
Oxidation - Hydroxylation 1 [3]
4''-Hydroxycannabidiol DM020030
53357352
Oxidation - Hydroxylation 1 [3]
5''-Hydroxycannabidiol DM020031
101621543
Oxidation - Hydroxylation 1 [3]
6alpha-Hydroxycannabidiol DM020026
53357350
Oxidation - Hydroxylation 1 [3]
6beta-Hydroxycannabidiol DM020025
53357351
Oxidation - Hydroxylation 1 [3]
7-OH-CBD DM000542
11301963
Oxidation - Hydroxylation 1 [3]
Cannabidiol-O-Glucuronide DM020032
163285562
Conjugation - Glucuronidation 1 [3]
7-Carboxy-Cannabidiol DM000543
146592489
Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002512 Cannabidiol 7-hydroxy-cannabidiol Oxidation - Hydroxylation CYP2C19 ... [3]
MR002513 Cannabidiol 6beta-Hydroxycannabidiol Oxidation - Hydroxylation CYP3A4 [3]
MR002514 Cannabidiol 6alpha-Hydroxycannabidiol Oxidation - Hydroxylation CYP3A4 [3]
MR002515 Cannabidiol 1''-Hydroxycannabidiol Oxidation - Hydroxylation Unclear [3]
MR002516 Cannabidiol 2''-Hydroxycannabidiol Oxidation - Hydroxylation CYP3A4 [3]
MR002517 Cannabidiol 3''-Hydroxycannabidiol Oxidation - Hydroxylation Unclear [3]
MR002518 Cannabidiol 4''-Hydroxycannabidiol Oxidation - Hydroxylation CYP3A4 [3]
MR002519 Cannabidiol 5''-Hydroxycannabidiol Oxidation - Hydroxylation Unclear [3]
MR002520 Cannabidiol Cannabidiol-O-Glucuronide Conjugation - Glucuronidation Unclear [3]
MR002511 7-hydroxy-cannabidiol 7-Carboxy-Cannabidiol Unclear Unclear [3]
⏷ Show the Full List of 10 MR(s)
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
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B17 (UGT2B17) DME0066 Homo sapiens
UDB17_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
⏷ Show the Full List of 15  DME(s)
References
1 Cannabidiol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells Chem Res Toxicol. 2003 Mar;16(3):336-49. doi: 10.1021/tx025599q.
3 Cytochrome P450-Catalyzed Metabolism of Cannabidiol to the Active Metabolite 7-Hydroxy-Cannabidiol Drug Metab Dispos. 2021 Oct;49(10):882-891. doi: 10.1124/dmd.120.000350.
4 Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95.
5 Glucuronidation of capsaicin by liver microsomes and expressed UGT enzymes: reaction kinetics, contribution of individual enzymes and marked species differences Expert Opin Drug Metab Toxicol. 2014 Oct;10(10):1325-36. doi: 10.1517/17425255.2014.954548.

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