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

General Information of Drug (ID: DR0268)
Drug Name
Capsaicin
Synonyms
Capsaicin; Capsaicin (JAN/USP); Capsaicin [USAN]; Axsain; CAPSAICINE; E-CAPSAICIN; Isodecenoic acid vanillylamide; NGX-4010; Qutenza; Styptysat; Transacin; Vanilloid; ZOSTRIX (TN); Zostrix; trans-Capsaicin; (E)-8-Methyl-N-vanillyl-6-nonenamide; (E)-Capsaicin; 404-86-4; 6-Nonenamide, 8-methyl-N-vanillyl-, (E)-; 8-Methyl-N-Vanillyl-6-Nonenamide; 8-Methyl-N-vanillyl-trans-6-nonenamide; C18H27NO3; CCRIS 1588; CHEBI:3374; Caswell No. 158; FEMA No. 3404; HSDB 954; NCI-C56564; NSC 56353; UNII-S07O44R1ZM; trans-8-Methyl-N-vanillyl-6-nonenamide
Indication Herpes zoster [ICD11: 1E91] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 305.4 Topological Polar Surface Area 58.6
Heavy Atom Count 22 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
1548943
PubChem SID
9083 ; 105773 ; 853800 ; 1916595 ; 7847316 ; 7978850 ; 8149724 ; 8653307 ; 10321304 ; 11537699 ; 12015395 ; 14923155 ; 17389996 ; 17486482 ; 22391501 ; 24847432 ; 24853014 ; 24853015 ; 24862158 ; 24896598 ; 26612181 ; 26680132 ; 26681474 ; 26744231 ; 26747263 ; 26747264 ; 26752818 ; 26752819 ; 26752820 ; 26758379 ; 29203915 ; 32248886 ; 46487934 ; 47216576 ; 47364983 ; 47515116 ; 47662075 ; 47662076 ; 47736251 ; 47736252 ; 47810544 ; 47885207 ; 48034884 ; 48259019 ; 48413373 ; 48423080 ; 48424925 ; 49688535 ; 49698675 ; 49747048
ChEBI ID
CHEBI:3374
CAS Number
404-86-4
TTD Drug ID
D0U5CE
Formula
C18H27NO3
Canonical SMILES
CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
InChI
1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChIKey
YKPUWZUDDOIDPM-SOFGYWHQSA-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
Capsaicin glucuronide DM000555 N. A. Conjugation - Glucuronidation 1 [3]
Capsaicin metabolite M1 DM000547 N. A. Oxidation - Dehydrogenation 1 [2]
Capsaicin metabolite M2 DM000548 N. A. Oxidation - Omega-Hydroxylation 1 [2]
Capsaicin metabolite M3 DM000549 N. A. Oxidation - Omega-1-Hydroxylation 1 [2]
Capsaicin metabolite M4 DM000550 N. A. Oxidation - Dehydrogenation 1 [2]
Capsaicin metabolite M5M7 DM000551 N. A. Oxidation - Hydroxylation 1 [2]
Capsaicin metabolite M6 DM000552 N. A. Oxidation - O-Dehydrogenation 1 [2]
Capsaicin metabolite M8 DM000553 N. A. Oxidation - N-Dehydrogenation; Oxygenation 1 [2]
Capsaicin metabolite M9 DM000554 N. A. Oxidation - N-Dehydrogenation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002818 Capsaicin Capsaicin metabolite M1 Oxidation - Dehydrogenation CYP2C19 ... [2]
MR002819 Capsaicin Capsaicin metabolite M2 Oxidation - Omega-Hydroxylation CYP2C19 ... [2]
MR002820 Capsaicin Capsaicin metabolite M3 Oxidation - Omega-1-Hydroxylation CYP2C19 ... [2]
MR002821 Capsaicin Capsaicin metabolite M4 Oxidation - Dehydrogenation CYP2C19 ... [2]
MR002822 Capsaicin Capsaicin metabolite M5M7 Oxidation - Hydroxylation CYP2C19 ... [2]
MR002823 Capsaicin Capsaicin metabolite M6 Oxidation - O-Dehydrogenation CYP2C19 ... [2]
MR002824 Capsaicin Capsaicin metabolite M8 Oxidation - N-Dehydrogenation; Oxygenation CYP2C19 ... [2]
MR002825 Capsaicin Capsaicin metabolite M9 Oxidation - N-Dehydrogenation CYP2C19 ... [2]
MR002826 Capsaicin Capsaicin glucuronide Conjugation - Glucuronidation UGT1A9 ... [3]
⏷ Show the Full List of 9 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
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_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
[2]
⏷ Show the Full List of 9  DME(s)
References
1 Capsaicin 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.
3 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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