General Information of Drug (ID: DR0548)
Drug Name
Dronabinol
Synonyms
Deltanyne; Dronabinol; Dronabinolum; Dronabinolum [Latin]; Marinol; Namisol; TETRAHYDROCANNABINOL; delta(1)-Tetrahydrocannabinol; delta(9)-THC; delta(9)-Tetrahydrocannabinol; delta(9)-Tetrahydrocannibinol; delta(sup 1)-Thc; delta(sup 9)-Thc; delta-9-THC; delta-9-tetrahydrocannabinol; delta1-THC; delta1-Tetrahydrocannabinol; delta9-THC; delta9-Tetrahydrocannabinol; (-)-delta9-trans-Tetrahydrocannabinol; 1-trans-delta-9-Tetrahydrocannabinol; 1-trans-delta9-Tetrahydrocannabinol; 9-tetrahydrocannabinol; Abbott 40566; THC
Indication Anorexia nervosa [ICD11: 6B80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 314.5 Topological Polar Surface Area 29.5
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
16078
PubChem SID
9186 ; 423124 ; 590069 ; 841255 ; 7847372 ; 7980767 ; 8162055 ; 12013925 ; 14776764 ; 14899056 ; 24900035 ; 24900224 ; 29283967 ; 46508472 ; 47289005 ; 48414516 ; 48422188 ; 49681167 ; 49855137 ; 53790103 ; 56311071 ; 56365468 ; 57288574 ; 57329243 ; 57654672 ; 68530527 ; 78512325 ; 93166585 ; 103167825 ; 103920666 ; 104338871 ; 113635228 ; 117426979 ; 127309746 ; 127309747 ; 127309748 ; 127309749 ; 127309750 ; 127309751 ; 127309752 ; 127309753 ; 127340561 ; 127340562 ; 127340563 ; 127340564 ; 127344438 ; 127696830 ; 134337522 ; 134339937 ; 134982169
ChEBI ID
CHEBI:66964
CAS Number
1972-08-3
TTD Drug ID
D0P1FO
Formula
C21H30O2
Canonical SMILES
CCCCCC1=CC2=C(C3C=C(CCC3C(O2)(C)C)C)C(=C1)O
InChI
1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChIKey
CYQFCXCEBYINGO-IAGOWNOFSA-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
11-Hydroxy-delta-9-THC DM006231
37482
Oxidation - 11-hydroxylation 1 [5] , [4] , [8] , [7]
11-OH-THC DM003198
644022
Oxidation - Aliphatic hydroxylation 1 [5] , [9]
7-beta-Hydroxy-delta-9-THC DM006237
131769990
Oxidation - 7-hydroxylation 1 [5]
7-OH-delta-9-Tetrahydrocannabinol DM006242
154699555
Oxidation - Aliphatic hydroxylation 1 [5] , [9]
7alpha-OH-delta-9-Tetrahydrocannabinol DM006243
154699556
Oxidation - Aliphatic hydroxylation 1 [5] , [9]
8-beta-Hydroxy-delta-9-THC DM006239
38041
Oxidation - 8-hydroxylation 1 [5]
8-Hydroxy-delta-9-THC DM006236
623131
Oxidation - 8-hydroxylation 1 [5]
8-OH-delta-9-Tetrahydrocannabinol DM006244
154699682
Unclear 1 [5] , [9]
8alpha-OH-delta-9-Tetrahydrocannabinol DM006245
154699681
Unclear 1 [5] , [9]
9-alpha,10-alpha-epoxyhexahydrocannabinol DM006240
125763
Oxidation - 9, 10-epoxidation 1 [5] , [7]
11-Hydroxy-delta-9-THC-glucuronide DM006234 N. A. Conjugation - Glucuronidation 2 [5]
11-Nor-9-carboxy-delta-9-THC DM006232
107885
Oxidation - Oxidationn 2 [5]
8,11-Dihydroxy-delta-9-THC DM006235
6420382
Oxidation - 8-hydroxylation 2 [5]
8,11-Dihydroxy-delta-9-THC DM006235
6420382
Oxidation - 11-hydroxylation 2 [5]
11-nor-9-carboxy-delta-9-THC-glucuronide DM006233 N. A. Conjugation - Glucuronidation 3 [5]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006686 Dronabinol 11-Hydroxy-delta-9-THC Oxidation - 11-hydroxylation CYP3A4 ... [5], [4], [8], [7]
MR006691 Dronabinol 8-Hydroxy-delta-9-THC Oxidation - 8-hydroxylation CYP3A4 [5]
MR006693 Dronabinol 7-beta-Hydroxy-delta-9-THC Oxidation - 7-hydroxylation CYP3A4 [5]
MR006694 Dronabinol 8-beta-Hydroxy-delta-9-THC Oxidation - 8-hydroxylation CYP3A4 [5]
MR006695 Dronabinol 9-alpha,10-alpha-epoxyhexahydrocannabinol Oxidation - 9, 10-epoxidation CYP3A4 ... [5], [7]
MR006696 Dronabinol 11-OH-delata-Tetrahydrocannabinol Oxidation - Aliphatic hydroxylation CYP3A4 ... [5], [9]
MR006697 Dronabinol 7-OH-delta-9-Tetrahydrocannabinol Oxidation - Aliphatic hydroxylation CYP3A4 [5], [9]
MR006698 Dronabinol 7alpha-OH-delta-9-Tetrahydrocannabinol Oxidation - Aliphatic hydroxylation Unclear [5], [9]
MR006699 Dronabinol 8-OH-delta-9-Tetrahydrocannabinol Unclear CYP3A4 [5], [9]
MR006700 Dronabinol 8alpha-OH-delta-9-Tetrahydrocannabinol Unclear CYP3A4 [5], [9]
MR013922 Dronabinol 7-alpha-Hydroxy-delta-9-THC Oxidation - 7-hydroxylation CYP3A4 [5]
MR006687 11-Hydroxy-delta-9-THC 11-Nor-9-carboxy-delta-9-THC Oxidation - Oxidationn CYP2C9 [5]
MR006689 11-Hydroxy-delta-9-THC 11-Hydroxy-delta-9-THC-glucuronide Conjugation - Glucuronidation UGT1A9 ... [5]
MR006690 11-Hydroxy-delta-9-THC 8,11-Dihydroxy-delta-9-THC Oxidation - 8-hydroxylation Unclear [5]
MR006692 8-Hydroxy-delta-9-THC 8,11-Dihydroxy-delta-9-THC Oxidation - 11-hydroxylation Unclear [5]
MR006688 11-Nor-9-carboxy-delta-9-THC 11-nor-9-carboxy-delta-9-THC-glucuronide Conjugation - Glucuronidation UGT1A1 ... [5]
⏷ Show the Full List of 16 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 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5] , [7]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[5]
⏷ Show the Full List of 9  DME(s)
References
1 Dronabinol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Increasing the intracellular availability of all-trans retinoic acid in neuroblastoma cells. Br J Cancer. 2005 Feb 28;92(4):696-704.
3 Health control over the feeding of troops on the Western and 3d Belorussian Fronts during the Great Patriotic War years. Voen Med Zh. 1975 Jun;(6):86-8.
4 CYP2C-catalyzed delta9-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin. Biochem Pharmacol. 2005 Oct 1;70(7):1096-103.
5 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.
6 Inhibition of cyclosporine and tetrahydrocannabinol metabolism by cannabidiol in mouse and human microsomes. Xenobiotica. 1996 Mar;26(3):275-84.
7 Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions
8 Characterization of human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes involved in the metabolism of classic cannabinoids
9 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.