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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL294199
CHEMBL294199
Compound Name CAPSAICIN
ChEMBL Synonyms CAPSAICIN | Qutenza
Max Phase 4 (Approved)
Trade Names Qutenza
Molecular Formula C18H27NO3

Additional synonyms for CHEMBL294199 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc(CNC(=O)CCCC\C=C\C(C)C)ccc1O
Standard InChI InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11- ...
Download InChI
Standard InChI Key YKPUWZUDDOIDPM-SOFGYWHQSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL294199

Molecule Features

CHEMBL294199 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Vanilloid receptor opener Vanilloid receptor FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
COUGHD003371HP:0012735COUGH1ClinicalTrials
CYSTINOSISD003554Orphanet:213CYSTINOSIS0ClinicalTrials
BACK PAIND001416EFO:0003843PAIN4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
WOUNDS AND INJURIESD014947EFO:0000546INJURY0ClinicalTrials
MUSCLE CRAMPD0091204
BURSITISD002062EFO:1000941FROZEN SHOULDER4DailyMed
MIGRAINE DISORDERSD008881EFO:0003821MIGRAINE DISORDER0ClinicalTrials
PAIND010146EFO:0003843PAIN3ClinicalTrials
PARKINSON DISEASED010300EFO:0002508PARKINSON'S DISEASE1ClinicalTrials
ANGINA, STABLED060050EFO:0003913ANGINA PECTORIS3ClinicalTrials
ARTHRALGIAD018771HP:0002829ARTHRALGIA4ATC
HYPERTENSION, PULMONARYD006976EFO:0001361PULMONARY HYPERTENSION2ClinicalTrials
LIPID METABOLISM DISORDERSD052439Orphanet:309005DISORDER OF LIPID METABOLISM2ClinicalTrials
ARTHRITISD001168EFO:0005856ARTHRITIS4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
PRURITUSD011537HP:0000989PRURITUS1ClinicalTrials
TENDINOPATHYD052256EFO:1001434TENDINOPATHY4DailyMed
AMYOTROPHIC LATERAL SCLEROSISD000690EFO:0000253AMYOTROPHIC LATERAL SCLEROSIS0ClinicalTrials
MYALGIAD063806HP:0003326MYALGIA4DailyMed
DailyMed
DailyMed
ATC
DailyMed
DailyMed
OSTEOARTHRITISD010003EFO:0002506OSTEOARTHRITIS3ClinicalTrials
PROSTATIC NEOPLASMSD011471EFO:0001663PROSTATE CARCINOMA2ClinicalTrials
DIABETIC NEUROPATHIESD003929EFO:1000783DIABETIC NEUROPATHY3ClinicalTrials

Clinical Data

ClinicalTrials.gov CAPSAICIN
The Cochrane Collaboration CAPSAICIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL294199. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.999
CHEMBL5102 Vanilloid receptor Rattus norvegicus 0.884
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.613
CHEMBL1860 Thyroid hormone receptor alpha Homo sapiens 0.259

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4497 NADH-ubiquinone oxidoreductase chain 1 Bos taurus 0.994
CHEMBL5102 Vanilloid receptor Rattus norvegicus 0.953
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.933
CHEMBL3724 Lysophosphatidic acid receptor Edg-4 Homo sapiens 0.530
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.493
CHEMBL335 Protein-tyrosine phosphatase 1B Homo sapiens 0.258

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
305.4 305.1991 3.91 9 58.56 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.76 - 3.22 3.22 1 22 0.54

Structural Alerts

There are 4 structural alerts for CHEMBL294199. To view alerts please click here.

Compound Cross References

ATC M - MUSCULO-SKELETAL SYSTEM
M02 - TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02A - TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02AB - Capsaicin and similar agents
M02AB01 - capsaicin

N - NERVOUS SYSTEM
N01 - ANESTHETICS
N01B - ANESTHETICS, LOCAL
N01BX - Other local anesthetics
N01BX04 - capsaicin

ChemSpider ChemSpider:YKPUWZUDDOIDPM-SOFGYWHQSA-N
DailyMed capsaicin
PubChem SID: 104171351 SID: 124883045 SID: 124883047 SID: 124883049 SID: 124883050 SID: 124890089 SID: 144204368 SID: 144207513 SID: 17389996 SID: 26747263 SID: 26752818 SID: 26752819 SID: 26752820 SID: 50105473 SID: 56463572
Wikipedia Capsaicin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL294199



ACToR 404-86-4
BindingDB 20461
Brenda 133152 1947 62314
ChEBI 3374
DrugBank DB06774
DrugCentral 3064
eMolecules 479469
EPA CompTox Dashboard DTXSID9020241
FDA SRS S07O44R1ZM
Guide to Pharmacology 2486
Human Metabolome Database HMDB0002227
KEGG Ligand C06866
LINCS LSM-43180
LipidMaps LMFA08020085
Mcule MCULE-8056866140
Metabolights MTBLC3374
MolPort MolPort-001-742-263
Nikkaji J1.529F J29.362H
NMRShiftDB 20248832
PDBe 4DY
PubChem 1548943
PubChem: Drugs of the Future 12015395
PubChem: Thomson Pharma 14923155
SureChEMBL SCHEMBL8085
ZINC ZINC000001530575

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/YKPUWZUDDOIDPM-SOFGYWHQSA-N spacer
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