Details of the Drug

General Information of Drug (ID: DMGMF6V)

Drug Name
Capsaicin
Synonyms Capsaicin (transdermal patch formulation, neuropathic pain)
Indication
Disease Entry ICD 11 Status REF
Back pain ME84.Z Approved [1]
Neuropathic pain 8E43.0 Approved [2]
Pain MG30-MG3Z Approved [1]
Peripheral neuropathy 8C0Z Approved [1]
Polyneuropathy N.A. Approved [1]
Postherpetic neuralgia 1E91.5 Approved [1]
Type-1/2 diabetes 5A10-5A11 Approved [1]
Diabetic neuropathy 8C0Z Investigative [1]
Neuralgia N.A. Investigative [1]
⏷ Show the Full List of Indication(s)
Affected Organisms
Humans and other mammals
ATC Code
M02AB01: Capsaicin
M02AB: Capsaicin and similar agents
M02A: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M: MUSCULO-SKELETAL SYSTEM
N01BX04: Capsaicin
N01BX: Other local anesthetics
N01B: ANESTHETICS, LOCAL
N01: ANESTHETICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 305.4
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1 h [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Elimination
In vivo animal studies demonstrates that less than 10 % of an administered dose was found in faces after 48 h [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 24.9 +/- 5.0 minutes [3]
Metabolism
The drug is metabolized via the liver [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.06 mg/mL [4]
Chemical Identifiers
Formula
C18H27NO3
IUPAC Name
(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Canonical SMILES
CC(C)/C=C/CCCCC(=O)NCC1=CC(=C(C=C1)O)OC
InChI
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
Cross-matching ID
PubChem CID
1548943
ChEBI ID
CHEMBL294199
CAS Number
404-86-4
UNII
S07O44R1ZM
DrugBank ID
DB06774
TTD ID
D0U5CE
INTEDE ID
DR0268
ACDINA ID
D00911
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Transient receptor potential cation channel V1 (TRPV1) TTMI6F5 TRPV1_HUMAN Agonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [6]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [6]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [6]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [6]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [6]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [6]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1) OT7TNF0L AAPK1_HUMAN Post-Translational Modifications [7]
5'-AMP-activated protein kinase catalytic subunit alpha-2 (PRKAA2) OTU1KZPV AAPK2_HUMAN Post-Translational Modifications [7]
5-hydroxytryptamine receptor 3A (HTR3A) OTAIV1AK 5HT3A_HUMAN Gene/Protein Processing [8]
Albumin (ALB) OTVMM513 ALBU_HUMAN Gene/Protein Processing [9]
Apolipoprotein C-I (APOC1) OTA58CED APOC1_HUMAN Gene/Protein Processing [10]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Protein Interaction/Cellular Processes [11]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [12]
Arrestin domain-containing protein 4 (ARRDC4) OTINJ0FX ARRD4_HUMAN Gene/Protein Processing [13]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [14]
Autophagy protein 5 (ATG5) OT4T5SMS ATG5_HUMAN Gene/Protein Processing [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Diethylene glycol monoethyl ether E00169 8146 Solubilizing agent; Solvent
Butylhydroxyanisole E00308 24667 Antimicrobial preservative; Antioxidant
Edetate disodium E00186 8759 Complexing agent
Polyethylene glycol 4000 E00654 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Sodium hydroxide E00234 14798 Alkalizing agent
Water E00035 962 Solvent
Silicone adhesive E00683 17317 Binding agent
Dimethicone 350 E00706 Not Available Antifoaming agent; Emollient; Water-repelling agent
Ethyl cellulose E00699 Not Available Coating agent; Microencapsulating agent; Binding agent; Diluent; Viscosity-controlling agent
⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Capsaicin 8% Patch 8% Patch Topical
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Capsaicin FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2486).
3 Unravelling the mystery of capsaicin: a tool to understand and treat pain. Pharmacol Rev. 2012 Oct;64(4):939-71. doi: 10.1124/pr.112.006163.
4 BDDCS applied to over 900 drugs
5 Capsaicin receptor: TRPV1 a promiscuous TRP channel. Handb Exp Pharmacol. 2007;(179):155-71.
6 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.
7 Capsaicin inhibits the migration, invasion and EMT of renal cancer cells by inducing AMPK/mTOR-mediated autophagy. Chem Biol Interact. 2022 Oct 1;366:110043. doi: 10.1016/j.cbi.2022.110043. Epub 2022 Aug 28.
8 Activation and modulation of recombinantly expressed serotonin receptor type 3A by terpenes and pungent substances. Biochem Biophys Res Commun. 2015 Nov 27;467(4):1090-6. doi: 10.1016/j.bbrc.2015.09.074. Epub 2015 Oct 9.
9 A comparative proteomic analysis for capsaicin-induced apoptosis between human hepatocarcinoma (HepG2) and human neuroblastoma (SK-N-SH) cells. Proteomics. 2008 Nov;8(22):4748-67. doi: 10.1002/pmic.200800094.
10 Induction of the endoplasmic reticulum stress protein GADD153/CHOP by capsaicin in prostate PC-3 cells: a microarray study. Biochem Biophys Res Commun. 2008 Aug 8;372(4):785-91.
11 Capsaicin induces apoptosis in SCC-4 human tongue cancer cells through mitochondria-dependent and -independent pathways. Environ Toxicol. 2012 May;27(6):332-41. doi: 10.1002/tox.20646. Epub 2010 Oct 5.
12 Triggering of transient receptor potential vanilloid type 1 (TRPV1) by capsaicin induces Fas/CD95-mediated apoptosis of urothelial cancer cells in an ATM-dependent manner. Carcinogenesis. 2009 Aug;30(8):1320-9. doi: 10.1093/carcin/bgp138. Epub 2009 Jun 5.
13 Neurotoxicity and underlying cellular changes of 21 mitochondrial respiratory chain inhibitors. Arch Toxicol. 2021 Feb;95(2):591-615. doi: 10.1007/s00204-020-02970-5. Epub 2021 Jan 29.
14 Effects of capsaicin on P-gp function and expression in Caco-2 cells. Biochem Pharmacol. 2006 Jun 14;71(12):1727-34. doi: 10.1016/j.bcp.2006.03.024. Epub 2006 Apr 18.
15 Role of autophagy in chemoresistance: regulation of the ATM-mediated DNA-damage signaling pathway through activation of DNA-PKcs and PARP-1. Biochem Pharmacol. 2012 Mar 15;83(6):747-57. doi: 10.1016/j.bcp.2011.12.029. Epub 2011 Dec 29.