Resiniferatoxin
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Resiniferatoxin
- DrugBank Accession Number
- DB06515
- Background
Resiniferatoxin (RTX) is a naturally occurring, ultrapotent capsaicin analog that activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain).
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 628.718
Monoisotopic: 628.267232868 - Chemical Formula
- C37H40O9
- Synonyms
- Resiniferatoxin
- RTX
Pharmacology
- Indication
Investigated for use/treatment in interstitial cystitis and urinary incontinence.
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTransient receptor potential cation channel subfamily V member 1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- A5O6P1UL4I
- CAS number
- 57444-62-9
- InChI Key
- DSDNAKHZNJAGHN-MXTYGGKSSA-N
- InChI
- InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3/t23-,27+,30-,33-,34-,35-,36-,37-/m1/s1
- IUPAC Name
- [(1R,2R,6R,10S,11R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
- SMILES
- [H][C@]12O[C@]3(CC4=CC=CC=C4)O[C@]1(C[C@@]([H])(C)[C@]1(O3)[C@]3([H])C=C(C)C(=O)[C@@]3(O)CC(COC(=O)CC3=CC(OC)=C(O)C=C3)=C[C@@]21[H])C(C)=C
References
- General References
- Szallasi A, Blumberg PM: Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper. Neuroscience. 1989;30(2):515-20. [Article]
- External Links
- PubChem Compound
- 104826
- ChemSpider
- 4642871
- BindingDB
- 50052442
- ChEMBL
- CHEMBL17976
- ZINC
- ZINC000004262463
- PDBe Ligand
- 6EU
- Wikipedia
- Resiniferatoxin
- PDB Entries
- 5irx / 6bwj / 6oo3 / 6oo4 / 6oo5 / 6oo7 / 7l2l / 7l2m / 7l2n / 7l2o … show 18 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Withdrawn Treatment Cancer Pain / Intractable Pain 1 3 Withdrawn Treatment Coronavirus Disease 2019 (COVID‑19) / Knee Pain Chronic / Osteoarthritis of the Knee 1 3 Withdrawn Treatment Knee Pain Chronic / Osteoarthritis of the Knee 1 2 Active Not Recruiting Treatment Knee Pain Chronic / Osteoarthritis of the Knee 1 2 Suspended Treatment Cancer Pain / Intractable Pain / Pain 1 1 Completed Treatment Intractable Cancer Pain 1 1 Completed Treatment Osteoarthritis of the Knee / Pain of the knee 1 1 Recruiting Treatment Intractable Pain / Palliative Treatment 1 1 Recruiting Treatment Morton's neuralgia 1 1, 2 Not Yet Recruiting Treatment Intractable Pain / Palliative Treatment 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00082 mg/mL ALOGPS logP 4.4 ALOGPS logP 5.59 Chemaxon logS -5.9 ALOGPS pKa (Strongest Acidic) 9.94 Chemaxon pKa (Strongest Basic) -3.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 120.75 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 170.1 m3·mol-1 Chemaxon Polarizability 66.87 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8464 Blood Brain Barrier + 0.599 Caco-2 permeable - 0.6017 P-glycoprotein substrate Substrate 0.8899 P-glycoprotein inhibitor I Inhibitor 0.7963 P-glycoprotein inhibitor II Non-inhibitor 0.5276 Renal organic cation transporter Non-inhibitor 0.8185 CYP450 2C9 substrate Non-substrate 0.859 CYP450 2D6 substrate Non-substrate 0.8467 CYP450 3A4 substrate Substrate 0.7345 CYP450 1A2 substrate Non-inhibitor 0.6836 CYP450 2C9 inhibitor Non-inhibitor 0.7855 CYP450 2D6 inhibitor Non-inhibitor 0.9175 CYP450 2C19 inhibitor Non-inhibitor 0.7399 CYP450 3A4 inhibitor Inhibitor 0.5918 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7577 Ames test Non AMES toxic 0.6839 Carcinogenicity Non-carcinogens 0.9378 Biodegradation Not ready biodegradable 0.9962 Rat acute toxicity 3.9178 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9381 hERG inhibition (predictor II) Non-inhibitor 0.6859
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets

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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
- Gene Name
- TRPV1
- Uniprot ID
- Q8NER1
- Uniprot Name
- Transient receptor potential cation channel subfamily V member 1
- Molecular Weight
- 94955.33 Da
References
- Szallasi A, Blumberg PM: Resiniferatoxin and its analogs provide novel insights into the pharmacology of the vanilloid (capsaicin) receptor. Life Sci. 1990;47(16):1399-408. [Article]
- Szallasi A, Conte B, Goso C, Blumberg PM, Manzini S: Characterization of a peripheral vanilloid (capsaicin) receptor in the urinary bladder of the rat. Life Sci. 1993;52(20):PL221-6. [Article]
- Nishihara K, Nozawa Y, Nakano M, Ajioka H, Matsuura N: Sensitizing effects of lafutidine on CGRP-containing afferent nerves in the rat stomach. Br J Pharmacol. 2002 Mar;135(6):1487-94. [Article]
Drug created at March 19, 2008 16:35 / Updated at February 21, 2021 18:52