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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

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.8 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
QUTENZA

Approved Use

Qutenza is indicated for the management of neuropathic pain associated with postherpetic neuralgia

Launch Date

1.2583296E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.38 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
4.36 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.64 h
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

Doses

DosePopulationAdverse events​
8 % single, topical
Recommended
Dose: 8 %
Route: topical
Route: single
Dose: 8 %
Sources: 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: Page: p.975
Disc. AE: Neuralgia...
AEs leading to
discontinuation/dose reduction:
Neuralgia (0.9%)
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: Page: p.1
Other AEs: Irritation of eyes, Respiratory tract irritation...
Other AEs:
Irritation of eyes
Respiratory tract irritation
Transient blood pressure increase
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Neuralgia 0.9%
Disc. AE
8 % single, topical
Recommended
Dose: 8 %
Route: topical
Route: single
Dose: 8 %
Sources: 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: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: Page: p.1
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
unlikely [IC50 12 uM]
unlikely [IC50 18 uM]
unlikely [IC50 2 uM]
unlikely [IC50 2.1 uM]
unlikely [IC50 24 uM]
unlikely [IC50 3.2 uM]
unlikely [IC50 >10 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Intraluminal capsaicin does not affect fluid and electrolyte absorption in the human jejunum but does cause pain.
1998 Aug
Activation of peripheral kappa opioid receptors inhibits capsaicin-induced thermal nociception in rhesus monkeys.
1999 Apr
Non-NMDA glutamate receptors modulate capsaicin induced c-fos expression within trigeminal nucleus caudalis.
1999 Jun
Neurokinin-1 receptors are involved in behavioral responses to high-intensity heat stimuli and capsaicin-induced hyperalgesia in mice.
1999 Jun
Effect of EMLA pre-treatment on capsaicin-induced burning and hyperalgesia.
1999 Mar
Capsaicin-sensitive C-fiber-mediated protective responses in ozone inhalation in rats.
1999 Mar
Effect of sympathetic activity on capsaicin-evoked pain, hyperalgesia, and vasodilatation.
1999 Mar 23
Capsaicin-sensitive afferent sensory nerves in modulating gastric mucosal defense against noxious agents.
1999 Nov
Sex differences in cholinergic analgesia II: differing mechanisms in two models of allodynia.
1999 Nov
Oral antinociception and oedema inhibition produced by NPC 18884, a non-peptidic bradykinin B2 receptor antagonist.
1999 Sep
Tourniquet constriction exacerbates hyperalgesia-related pain induced by intradermal capsaicin injection.
1999 Sep
Tachykinins in the porcine pancreas: potent exocrine and endocrine effects via NK-1 receptors.
2000 Apr
Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis.
2000 Apr
Involvement of glutamate in transmission of afferent constrictive inputs from the airways to the nucleus tractus solitarius in ferrets.
2000 Apr 12
Effect of ginsenosides, active components of ginseng, on capsaicin-induced pain-related behavior.
2000 Aug 23
Importance of endogenous nitric oxide synthase in the rat hypothalamus and amygdala in mediating the response to capsaicin.
2000 Aug 7
Antinociceptive profile of hodgkinsine.
2000 Dec
Induction of vanilloid receptor channel activity by protein kinase C.
2000 Dec 21-28
Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial.
2000 Jan
Relative potency of epidural to intrathecal clonidine differs between acute thermal pain and capsaicin-induced allodynia.
2000 Jan
Antinociceptive properties of the methanolic extract and two triterpenes isolated from Epidendrum Mosenii stems (Orchidaceae).
2000 Jan 21
ATP in human skin elicits a dose-related pain response which is potentiated under conditions of hyperalgesia.
2000 Jun
Encoding of burning pain from capsaicin-treated human skin in two categories of unmyelinated nerve fibres.
2000 Mar
Spatial mapping of the zone of secondary hyperalgesia reveals a gradual decline of pain with distance but sharp borders.
2000 May
Capsaicin protects against ethanol-induced oxidative injury in the gastric mucosa of rats.
2000 Nov 10
The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism.
2001 Apr 20
Capsaicin-induced apoptosis in SK-Hep-1 hepatocarcinoma cells involves Bcl-2 downregulation and caspase-3 activation.
2001 Apr 26
Effects of vanilloid receptor agonists and antagonists on gastric antral ulcers in rats.
2001 Dec 7
Chronic tobacco smoke exposure increases airway sensitivity to capsaicin in awake guinea pigs.
2001 Feb
Analysis of the native quaternary structure of vanilloid receptor 1.
2001 Jul 27
Transient inhibition of the human motor cortex by capsaicin-induced pain. A study with transcranial magnetic stimulation.
2001 Nov 13
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
2001 Sep
Delayed cardioprotection induced by nitroglycerin is mediated by alpha-calcitonin gene-related peptide.
2002 Apr
Suppression of phorbol ester-induced NF-kappaB activation by capsaicin in cultured human promyelocytic leukemia cells.
2002 Aug
Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia.
2002 Aug
Role of bradykinin in acid-induced mesenteric hyperemia and duodenal villous damage.
2002 Jan 4
5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis.
2002 Jun
The orofacial capsaicin test in rats: effects of different capsaicin concentrations and morphine.
2002 Mar
The effect of chronic oral desipramine on capsaicin-induced allodynia and hyperalgesia: a double-blinded, placebo-controlled, crossover study.
2002 Oct
High affinity antagonists of the vanilloid receptor.
2002 Oct
Deficits in visceral pain and referred hyperalgesia in Nav1.8 (SNS/PN3)-null mice.
2002 Oct 1
Naloxone increases pain induced by topical capsaicin in healthy human volunteers.
2002 Sep
A comparison of hyperalgesia and neurogenic inflammation induced by melittin and capsaicin in humans.
2003 Feb 13
Patents

Sample Use Guides

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 UTC 2023
Edited
by admin
on Sat Dec 16 14:11:29 UTC 2023
Record UNII
0892508P5Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOCACAPSAICIN HYDROCHLORIDE
USAN  
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
Created by admin on Sat Dec 16 14:11:30 UTC 2023 , Edited by admin on Sat Dec 16 14:11:30 UTC 2023
PRIMARY
SMS_ID
300000044543
Created by admin on Sat Dec 16 14:11:30 UTC 2023 , Edited by admin on Sat Dec 16 14:11:30 UTC 2023
PRIMARY
CAS
1931116-92-5
Created by admin on Sat Dec 16 14:11:30 UTC 2023 , Edited by admin on Sat Dec 16 14:11:30 UTC 2023
PRIMARY
NCI_THESAURUS
C175207
Created by admin on Sat Dec 16 14:11:30 UTC 2023 , Edited by admin on Sat Dec 16 14:11:30 UTC 2023
PRIMARY
USAN
GH-102
Created by admin on Sat Dec 16 14:11:30 UTC 2023 , Edited by admin on Sat Dec 16 14:11:30 UTC 2023
PRIMARY
FDA UNII
0892508P5Q
Created by admin on Sat Dec 16 14:11:30 UTC 2023 , Edited by admin on Sat Dec 16 14:11:30 UTC 2023
PRIMARY
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