General
Preferred name
CAPSAICIN
Synonyms
CHEMBL294199 ()
(E)-Capsaicin ()
8-Methyl-N-vanillyl-trans-6-nonenamide ()
Qutenza ()
Vanilloid ()
Zostrix ()
8-Methyl-N-vanillyl-trans-6-nonenamide(E)-Capsaicin ()
Capsaicinoid ()
Capsaicin(Vanilloid) ()
Qutenza, Vanilloid ()
Mioton ()
Trans-capsaicin ()
FEMA NO. 3404 ()
ALGRX-4975 ()
Capzasin-hp ()
NGX-1998 ()
Axsain ()
Cntx-4975 ()
ALGRX 4975 ()
Dolenon ()
Ausanil ()
Togarashi orenji ()
Zostrix HP ()
Ratden pe 40 ()
NGX-4010 ()
NSC-56353 ()
Zacin ()
Ovocap ()
Capsaicin (technical grade) ()
Capsaicin-d3 ()
P&D ID
PD001884
CAS
404-86-4
1217899-52-9
Tags
probe
natural product
drug
available
Approved by
FDA
First approval
2009
Drug Status
approved
Drug indication
Antineuralgic, Specific Pain Syndromes, Topical
Neuropathic pain
Analgesic (topical)
Max Phase
Phase 4
Probe info
Probe selectivity
protein-selective
Probe type
P&D approved
calculated probe
Probe sources
High-quality chemical probes
Tool Compound Set
Probe targets
[[ compound.targets[t].gene_name ]]
Probe control
Probe control not defined
Orthogonal probes
1
No orthogonal probes found
Similar probes
1
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
TOXICITY
Acute oral LD50 and dermal LD50 in mouse are 47.2 mg/kg and >512 mg/kg, respectively [MSDS]. Capsaicin is shown to be mutagenic for bacteria and yeast [MSDS].; ; Capsaicin can cause serious irritation, conjunctivitis and lacrimation via contact with eyes. It induces a burning sensation and pain in case of contact with eyes and skin. As it is also irritating to the respiratory system, it causes lung irritation and coughing as well as bronchoconstriction. Other respiratory effects include laryngospasm, swelling of the larynx and lungs, chemical pneumonitis,respiratory arrest and central nervous system effects such as convulsions and excitement [L1944]. In case of ingestion, gastrointestinal tract irritation may be observed along with a sensation of warmth or painful burning [MSDS]. Symptoms of systemic toxicity include disorientation, fear, loss of body motor control including diminished hand-eye coordination, hyperventilation, tachycardia, and pulmonary oedema [L1944]. Careful early decontamination is recommended and medical intervention should be initiated for any life-threatening symptoms. In case of contact, individual must be removed from the source of exposure and the contacted skin and mucous membranes should be thoroughly washed with copious amounts of water [L1944].
DESCRIPTION
Although capsaicin was approved by the US FDA in 2009, this compound was previously marketed so was not subject to a New Drug Application.
(GtoPdb)
ABSORPTION
**Oral**: Following oral administration, capsaicin may be absorbed by a nonactive process from the stomach and whole intestine with an extent of absorption ranging between 50 and 90%, depending on the animal [A32319]. The peak blood concentration can be reached within 1 hour following administration [A32319]. Capsaicin may undergo minor metabolism in the small intestine epithelial cells post-absorption from the stomach into the small intestines. While oral pharmacokinetics information in humans is limited, ingestion of equipotent dose of 26.6 mg of pure capsaicin, capsaicin was detected in the plasma after 10 minutes and the peak plasma concentration of 2.47 ± 0.13 ng/ml was reached at 47.1 ± 2.0 minutes [A32319].; ; **Systemic**: Following intravenous or subcutaneous administration in animals, the concentrations in the brain and spinal cord were approximately 5-fold higher than that in blood and the concentration in the liver was approximately 3-fold higher than that in blood [A32319]. ; ; **Topical**: Topical capsaicin in humans is rapidly and well absorbed through the skin, however systemic absorption following topical or transdermal administration is unlikely [A32319]. For patients receiving the topical patch containing 179 mg of capsaicin, a population analysis was performed and plasma concentrations of capsaicin were fitted using a one-compartment model with first-order absorption and linear elimination. The mean peak plasma concentration was 1.86 ng/mL but the maximum value observed in any patient was 17.8 ng/mL [A32319].
DESCRIPTION
Prototypic vanilloid receptor agonist
(Tocriscreen Total)
DESCRIPTION
Vanilloid receptor antagonist; also activator of ENaCdelta
(Tocris Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
8
Organisms
2
Compound Sets
30
AdooQ Bioactive Compound Library
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
High-quality chemical probes
LSP-MoA library (Laboratory of Systems Pharmacology)
Mcule NIBR MoA Box Subset
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
Tocriscreen Total
Tool Compound Set
ZINC Tool Compounds
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
55
Molecular Weight
305.2
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
9
Ring Count
1
Aromatic Ring Count
1
cLogP
3.79
TPSA
58.56
Fraction CSP3
0.5
Chiral centers
0.0
Largest ring
6.0
QED
0.54
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Vanilloid receptor
hTRPV1( in HEK293 cell)
CFTR, TRPV1
Endogenous Metabolite
TRP Channel
Pathway
Membrane Transporter/Ion Channel
Apoptosis
Autophagy
Metabolic Enzyme/Protease
Neuronal Signaling
Primary Target
TRPV
MOA
TRP/TRPV Channel agonist
Agonist
Vanilloid receptor agonist
TRPV agonist
Member status
member
Indication
muscle pain, rheumatoid arthritis
Disease Area
neurology/psychiatry, rheumatology
Source data
