VOCACAPSAICIN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H41N3O4.ClH
Molecular Weight	496.082
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of VOCACAPSAICIN HYDROCHLORIDE

Structure Search

SMILES

Cl.CNCC1CCCCN1C(=O)OC2=CC=C(CNC(=O)CCCC\C=C\C(C)C)C=C2OC

InChI

InChIKey=WOJDHHAJADLOCK-RVDQCCQOSA-N

InChI=1S/C26H41N3O4.ClH/c1-20(2)11-7-5-6-8-13-25(30)28-18-21-14-15-23(24(17-21)32-4)33-26(31)29-16-10-9-12-22(29)19-27-3;/h7,11,14-15,17,20,22,27H,5-6,8-10,12-13,16,18-19H2,1-4H3,(H,28,30);1H/b11-7+;

HIDE SMILES / InChI

Molecular Formula	C26H41N3O4
Molecular Weight	459.6214
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/capsaicin-topical.html http://www.rxlist.com/qutenza-drug.htm http://www.wikidoc.org/index.php/Capsaicin

Capsaicin is a topical analgesic that is FDA approved for the treatment of neuropathic pain associated with postherpetic neuralgia. Capsaicin is most often used as a topical analgesic and exists in many formulations of cream, liquid, and patch preparations of various strengths; however, it may also be found in some dietary supplements. Capsaicin is a naturally-occurring botanical irritant in chili peppers, synthetically derived for pharmaceutical formulations. Capsaicin is an agonist for the transient receptor potential vanilloid I receptor (TRPVI), which is an ion channel-receptor complex expressed on nociceptive nerve fibers in the skin. Common adverse reactions include erythema, rash, pruritus, nausea.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16056236 \| http://www.drugbank.ca/drugs/DB06774	Agonist 2678		1.8 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Neuropathic pain associated with postherpetic neuralgia 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	Palliative		Approved 8429	QUTENZA Approved Use Qutenza is indicated for the management of neuropathic pain associated with postherpetic neuralgia Launch Date 2009

C_max

Value	Dose	Co-administered	Analyte	Population
1.38 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19494795/	640 μg/cm² single, topical dose: 640 μg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CAPSAICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4.36 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19494795/	640 μg/cm² single, topical dose: 640 μg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CAPSAICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.64 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19494795/	640 μg/cm² single, topical dose: 640 μg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CAPSAICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 % single, topical Recommended Dose: 8 % Route: topical Route: single Dose: 8 % Sources: https://pubmed.ncbi.nlm.nih.gov/20655809 Page: p.975	unhealthy, 71.6 +/-10.27 n = 222 Health Status: unhealthy Condition: Neuropathic pain associated with postherpetic neuralgia Age Group: 71.6 +/-10.27 Sex: M+F Population Size: 222 Sources: https://pubmed.ncbi.nlm.nih.gov/20655809 Page: p.975	Disc. AE: Neuralgia... AEs leading to discontinuation/dose reduction: Neuralgia (0.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/20655809 Page: p.975
8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Neuropathic pain associated with postherpetic neuralgia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1	Other AEs: Irritation of eyes, Respiratory tract irritation... Other AEs: Irritation of eyes Respiratory tract irritation Transient blood pressure increase Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Neuralgia	0.9% Disc. AE	8 % single, topical Recommended Dose: 8 % Route: topical Route: single Dose: 8 % Sources: https://pubmed.ncbi.nlm.nih.gov/20655809 Page: p.975	unhealthy, 71.6 +/-10.27 n = 222 Health Status: unhealthy Condition: Neuropathic pain associated with postherpetic neuralgia Age Group: 71.6 +/-10.27 Sex: M+F Population Size: 222 Sources: https://pubmed.ncbi.nlm.nih.gov/20655809 Page: p.975
Irritation of eyes		8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Neuropathic pain associated with postherpetic neuralgia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1
Respiratory tract irritation		8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Neuropathic pain associated with postherpetic neuralgia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1
Transient blood pressure increase		8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Neuropathic pain associated with postherpetic neuralgia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1037 inhibitor 1767 inducer 389	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C19 1478 CYP2E1 882 CYP3A4/5 278	CYP2C19 991	CYP1A2 701 CYP2B6 547 CYP2C19 293 CYP2E1 128 CYP3A4/5 124

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2C19 1553	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2E1 970	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP3A4/5 335	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 12 uM]	trans-capsaicin 4
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 18 uM]	trans-capsaicin 4
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 2 uM]	trans-capsaicin 4
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 2.1 uM]	trans-capsaicin 4
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 24 uM]	trans-capsaicin 4
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 3.2 uM]	trans-capsaicin 4
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 >10 uM]	trans-capsaicin 4

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=22 Page: 22.0	major
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=22 Page: 22.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3374	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3374
ChemicalBook	CB32551563	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB32551563
ChemicalBook	CB6112967	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6112967
MolPort	MolPort-001-742-263	https://www.molport.com/shop/molecule-link/MolPort-001-742-263
ZINC	ZINC000001530575	http://zinc15.docking.org/substances/ZINC000001530575
eMolecules	479469	https://www.emolecules.com/cgi-bin/more?vid=479469

PubMed

Title	Date	PubMed
Intraluminal capsaicin does not affect fluid and electrolyte absorption in the human jejunum but does cause pain.	1998 Aug	10189853
Non-NMDA glutamate receptors modulate capsaicin induced c-fos expression within trigeminal nucleus caudalis.	1999 Jun	10401552
Effect of zafirlukast on cough reflex sensitivity in asthmatics.	1999 May	10350223
Oral antinociception and oedema inhibition produced by NPC 18884, a non-peptidic bradykinin B2 receptor antagonist.	1999 Sep	10543429
Effect of ginsenosides, active components of ginseng, on capsaicin-induced pain-related behavior.	2000 Aug 23	10963761
Antinociceptive profile of hodgkinsine.	2000 Dec	11199142
Differential effects of systemically administered ketamine and lidocaine on dynamic and static hyperalgesia induced by intradermal capsaicin in humans.	2000 Feb	10743446
Peripheral lidocaine but not ketamine inhibits capsaicin-induced hyperalgesia in humans.	2000 Oct	11064608
Antinociceptive properties of extracts of new species of plants of the genus Phyllanthus (Euphorbiaceae).	2000 Sep	10967476
The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism.	2001 Apr 20	11278420
Capsaicin-induced apoptosis in SK-Hep-1 hepatocarcinoma cells involves Bcl-2 downregulation and caspase-3 activation.	2001 Apr 26	11275362
Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide.	2001 Dec	11744139
Nerve growth factor regulates VR-1 mRNA levels in cultures of adult dorsal root ganglion neurons.	2001 Jan	11166474
Antinociceptive effects of delta-opioid agonists in Rhesus monkeys: effects on chemically induced thermal hypersensitivity.	2001 Mar	11181927
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.	2001 Oct	11606325
Capsaicin as a source for painful stimulation in functional MRI.	2001 Oct	11599056
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.	2001 Sep	11514089
Intestinal protection by lafutidine, a histamine H(2)-receptor antagonist, against indomethacin-induced damage in rats--role of endogenous nitric oxide.	2001 Sep-Oct	11535926
Heat hyperalgesia in humans: assessed by different stimulus temperature profiles.	2002	12160510
Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats.	2002 Apr	12024109
Activation of spinal ORL-1 receptors prevents acute cutaneous neurogenic inflammation: role of nociceptin-induced suppression of primary afferent depolarization.	2002 Apr	11973003
Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia.	2002 Aug	12122501
Preliminary efficacy assessment of intrathecal injection of an American formulation of adenosine in humans.	2002 Jan	11752998
Acupuncture modulation of capsaicin-induced inflammation: effect of intraperitoneal and local administration of naloxone in rats. A blinded controlled study.	2002 Jun	12165192
5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis.	2002 Jun	12110114
The orofacial capsaicin test in rats: effects of different capsaicin concentrations and morphine.	2002 Mar	11932064
HSP90 inhibitors alter capsaicin- and ATP-induced currents in rat dorsal root ganglion neurons.	2002 Mar 25	11930156
Assessment of the reproducibility of intradermal administration of capsaicin as a model for inducing human pain.	2002 Sep	12237211
Naloxone increases pain induced by topical capsaicin in healthy human volunteers.	2002 Sep	12237198
Opioid-insensitive hypoalgesia to mechanical stimuli at sites ipsilateral and contralateral to experimental muscle pain in human volunteers.	2002 Sep	12195523
Phosphorylation of extracellular signal-regulated kinase in primary afferent neurons by noxious stimuli and its involvement in peripheral sensitization.	2002 Sep 1	12196597
Prostaglandin and protein kinase A-dependent modulation of vanilloid receptor function by metabotropic glutamate receptor 5: potential mechanism for thermal hyperalgesia.	2002 Sep 1	12196566

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose of Qutenza is a single, 60-minute application of up to four patches. Qutenza patch contains 8% capsaicin (640 mcg/cm2).

Route of Administration: Topical

In Vitro Use Guide

In isolated perfused globally ischemic rat hearts, antiischemic efficacy was assessed as a significant extension (36% and 50%) in time to contracture with 30 microM capsaicin and 1 microM diltiazem, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:11:29 GMT 2023` Edited by `admin` on `Sat Dec 16 14:11:29 GMT 2023`
Record UNII	0892508P5Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VOCACAPSAICIN HYDROCHLORIDE

Official Name

English

1-PIPERIDINECARBOXYLIC ACID, 2-((METHYLAMINO)METHYL)-, 2-METHOXY-4-((((6E)-8-METHYL-1-OXO-6-NONEN-1-YL)AMINO)METHYL)PHENYL ESTER, HYDROCHLORIDE (1:1)

Systematic Name

English

CA-008 HYDROCHLORIDE

Code

English

2-Methoxy-4-{[(6E)-8-methylnon-6-enamido]methyl}phenyl (2RS)-2-[(methylamino)methyl]piperidine-1-carboxylate, hydrochloride (1:1)

Systematic Name

English

VOCACAPSAICIN HYDROCHLORIDE [USAN]

Common Name

English

Code System Code Type Description

PUBCHEM

132169136