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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

Description

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 TargetPharmacologyConditionPotency
1.8 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
QUTENZA

Cmax

ValueDoseCo-administeredAnalytePopulation
1.38 ng/mL
640 μg/cm² single, topical
CAPSAICIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4.36 ng × h/mL
640 μg/cm² single, topical
CAPSAICIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.64 h
640 μg/cm² single, topical
CAPSAICIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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.