Resiniferatoxin

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
TargetActionsOrganism
UTransient receptor potential cation channel subfamily V member 1Not AvailableHumans
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
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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
  1. 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]
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
PhaseStatusPurposeConditionsCount
3WithdrawnTreatmentCancer Pain / Intractable Pain1
3WithdrawnTreatmentCoronavirus Disease 2019 (COVID‑19) / Knee Pain Chronic / Osteoarthritis of the Knee1
3WithdrawnTreatmentKnee Pain Chronic / Osteoarthritis of the Knee1
2Active Not RecruitingTreatmentKnee Pain Chronic / Osteoarthritis of the Knee1
2SuspendedTreatmentCancer Pain / Intractable Pain / Pain1

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
PropertyValueSource
Water Solubility0.00082 mg/mLALOGPS
logP4.4ALOGPS
logP5.59Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)9.94Chemaxon
pKa (Strongest Basic)-3.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area120.75 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity170.1 m3·mol-1Chemaxon
Polarizability66.87 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8464
Blood Brain Barrier+0.599
Caco-2 permeable-0.6017
P-glycoprotein substrateSubstrate0.8899
P-glycoprotein inhibitor IInhibitor0.7963
P-glycoprotein inhibitor IINon-inhibitor0.5276
Renal organic cation transporterNon-inhibitor0.8185
CYP450 2C9 substrateNon-substrate0.859
CYP450 2D6 substrateNon-substrate0.8467
CYP450 3A4 substrateSubstrate0.7345
CYP450 1A2 substrateNon-inhibitor0.6836
CYP450 2C9 inhibitorNon-inhibitor0.7855
CYP450 2D6 inhibitorNon-inhibitor0.9175
CYP450 2C19 inhibitorNon-inhibitor0.7399
CYP450 3A4 inhibitorInhibitor0.5918
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7577
Ames testNon AMES toxic0.6839
CarcinogenicityNon-carcinogens0.9378
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity3.9178 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9381
hERG inhibition (predictor II)Non-inhibitor0.6859
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-0000009000-582a377b54ff98032a1b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0200009000-10399cf8e90e3e610536
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000179000-c65306e2838db80545b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05r0-2900438000-d80349f31c530149f1c0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0500179000-21bf5f84a0fbddda7abb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dj-1800194000-bff210493d3cde17ed90
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-249.3833541
predicted
DarkChem Lite v0.1.0
[M+H]+251.5143541
predicted
DarkChem Lite v0.1.0
[M+Na]+247.6733541
predicted
DarkChem Lite v0.1.0

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
  1. 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]
  2. 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]
  3. 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