RESINIFERATOXIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H40O9
Molecular Weight	628.7081
Optical Activity	( + )
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12O[C@]4(CC3=CC=CC=C3)O[C@]1(C[C@@H](C)[C@]5(O4)[C@]6([H])C=C(C)C(=O)[C@@]6(O)CC(COC(=O)CC7=CC=C(O)C(OC)=C7)=C[C@@]25[H])C(C)=C

InChI

InChIKey=DSDNAKHZNJAGHN-MXTYGGKSSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27743486 | https://www.ncbi.nlm.nih.gov/pubmed/29320813 | https://clinicaltrials.gov/ct2/show/NCT00804154 | https://clinicaltrials.gov/ct2/show/NCT03542838

Resiniferatoxin (RTX or RTX-107) is a vanilloid derived from a cactus-like plant (Euphoria resiniferous) and has anti-inflammatory activity. This compound is an agonist of the transient receptor potential vanilloid 1 (TRPV1). Resiniferatoxin produces analgesia by desensitizing the TRPV1 receptor. Findings of several studies have suggested a potential therapeutic use of the anti-inflammatory effect of resiniferatoxin. Phase I and II clinical trials have been completed or are underway, evaluating the safety and efficacy of resiniferatoxin in pain-related disorders such as osteoarthritis and cancers.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27563913	Agonist 2678

PubMed

Title	Date	PubMed
Regulation of neuropeptide release from pulmonary capsaicin-sensitive afferents in relation to bronchoconstriction.	1993	7694442
Induction of apoptosis by vanilloid compounds does not require de novo gene transcription and activator protein 1 activity.	1998 Mar	9580328
Anandamide-evoked activation of vanilloid receptor 1 contributes to the development of bladder hyperreflexia and nociceptive transmission to spinal dorsal horn neurons in cystitis.	2004 Dec 15	15601931
Ischemic preconditioning of remote organs attenuates gastric ischemia-reperfusion injury through involvement of prostaglandins and sensory nerves.	2004 Sep 19	15363968
Capsaicin-sensitive sensory fibers in the islets of Langerhans contribute to defective insulin secretion in Zucker diabetic rat, an animal model for some aspects of human type 2 diabetes.	2007 Jan	17241282
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.	2007 Jan 15	17038422
Human keratinocytes are vanilloid resistant.	2008	18852901
Enhancement of cutaneous nerve regeneration by 4-methylcatechol in resiniferatoxin-induced neuropathy.	2008 Feb	18219259
Preventive effect of TRPV1 agonists capsaicin and resiniferatoxin on ischemia/reperfusion-induced renal injury in rats.	2008 May	18460982
Differential effects of substance P or hemokinin-1 on transient receptor potential channels, TRPV1, TRPA1 and TRPM8, in the rat.	2010 Feb	19926130
Activation of TRPV1 reduces vascular lipid accumulation and attenuates atherosclerosis.	2011 Dec 1	21908651
Resiniferatoxin induces death of bladder cancer cells associated with mitochondrial dysfunction and reduces tumor growth in a xenograft mouse model.	2014 Dec 5	25451591

Name

Type

Language

RESINIFERATOXIN

Official Name

English

Resiniferatoxin [WHO-DD]

Common Name

English

BENZENEACETIC ACID, 4-HYDROXY-3-METHOXY-, ((2S,3AR,3BS,6AR,9AR,9BR,10R,11AR)-3A,3B,6,6A,9A,10,11,11A-OCTAHYDRO-6A-HYDROXY-8,10-DIMETHYL-11A-(1-METHYLETHENYL)-7-OXO-2-(PHENYLMETHYL)-7H-2,9B-EPOXYAZULENO(5,4-E)-1,3-BENZODIOXOL-5-YL)METHYL ESTER

Common Name

English

(+)-RESINIFERATOXIN

Common Name

English

resiniferatoxin [INN]

Common Name

English

RESINIFERATOXIN [USAN]

Common Name

English

LOPAIN

Brand Name

English

[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-Benzyl-6a-hydroxy-8,10-dimethyl-11a-(prop-1-en-2-yl)-7-oxo-3a,6,6a,7,9a,10,11,11a-octahydro-3bH-2,9b-epoxyazuleno[5,4-E]-1,3-benzodioxol-5-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

Systematic Name

English

MTX-071

Common Name

English

MTX-71

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C2198