VOCACAPSAICIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H41N3O4
Molecular Weight	459.6214
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BXAQOVOOXOHMFY-YRNVUSSQSA-N

InChI=1S/C26H41N3O4/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)/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	( + / - )

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
Topical EMLA pre-treatment fails to decrease the pain induced by 1% topical capsaicin.	1999 Apr	10342425
Brain processing of capsaicin-induced secondary hyperalgesia: a functional MRI study.	1999 Aug 11	10449119
Effect of EMLA pre-treatment on capsaicin-induced burning and hyperalgesia.	1999 Mar	10228629
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
Tachykinins in the porcine pancreas: potent exocrine and endocrine effects via NK-1 receptors.	2000 Apr	10766449
Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis.	2000 Apr	10749792
Importance of endogenous nitric oxide synthase in the rat hypothalamus and amygdala in mediating the response to capsaicin.	2000 Aug 7	10880996
Activation of the somatosensory cortex during Abeta-fiber mediated hyperalgesia. A MSI study.	2000 Jul 14	10882785
ATP in human skin elicits a dose-related pain response which is potentiated under conditions of hyperalgesia.	2000 Jun	10825361
Spatial mapping of the zone of secondary hyperalgesia reveals a gradual decline of pain with distance but sharp borders.	2000 May	10779658
Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide.	2001 Dec	11744139
Role of central and peripheral tachykinin NK1 receptors in capsaicin-induced pain and hyperalgesia in mice.	2001 Feb 1	11166975
Nerve growth factor regulates VR-1 mRNA levels in cultures of adult dorsal root ganglion neurons.	2001 Jan	11166474
Analysis of the native quaternary structure of vanilloid receptor 1.	2001 Jul 27	11358970
The heme oxygenase-1 pathway is involved in calcitonin gene-related peptide-mediated delayed cardioprotection induced by monophosphoryl lipid A in rats.	2002 Jan 15	11738242
The role of the gastric afferent vagal nerve in ghrelin-induced feeding and growth hormone secretion in rats.	2002 Oct	12360474
Phosphorylation of extracellular signal-regulated kinase in primary afferent neurons by noxious stimuli and its involvement in peripheral sensitization.	2002 Sep 1	12196597

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 14:11:30 GMT 2023` Edited by `admin` on `Sat Dec 16 14:11:30 GMT 2023`
Record UNII	KRJ8H9BOG7
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VOCACAPSAICIN

Official Name

English

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

Systematic Name

English

CA-008

Code

English

VOCACAPSAICIN [USAN]

Common Name

English

vocacapsaicin [INN]

Common Name

English

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

Systematic Name

English

Code System Code Type Description

SMS_ID

300000027512