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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:3374
CAS Number: 404-86-4
DrugBank ID: DB06774
TTD ID: D0U5CE
INTEDE ID: DR0268
ACDINA ID: D00911

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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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]

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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]
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[10]
Angiopoietin-1 (ANGPT1)	OTVZ1NG3	ANGP1_HUMAN	Gene/Protein Processing	[11]
Angiopoietin-1 receptor (TEK)	OT78YN57	TIE2_HUMAN	Gene/Protein Processing	[11]
Angiopoietin-2 (ANGPT2)	OTEQK65P	ANGP2_HUMAN	Gene/Protein Processing	[11]
Apolipoprotein C-I (APOC1)	OTA58CED	APOC1_HUMAN	Gene/Protein Processing	[12]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Capsaicin 8% Patch	8%	Patch	Topical

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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	Capsaicin, a component of red peppers, induces expression of androgen receptor via PI3K and MAPK pathways in prostate LNCaP cells. FEBS Lett. 2009 Jan 5;583(1):141-7. doi: 10.1016/j.febslet.2008.11.038. Epub 2008 Dec 6.
11	Capsaicin promotes a more aggressive gene expression phenotype and invasiveness in null-TRPV1 urothelial cancer cells. Carcinogenesis. 2011 May;32(5):686-94. doi: 10.1093/carcin/bgr025. Epub 2011 Feb 10.
12	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.
13	TRPV6 mediates capsaicin-induced apoptosis in gastric cancer cells--Mechanisms behind a possible new "hot" cancer treatment. Biochim Biophys Acta. 2007 Apr;1773(4):565-76. doi: 10.1016/j.bbamcr.2007.01.001. Epub 2007 Jan 10.