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

Molecular Formula	C37H40O9
Molecular Weight	628.7081
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Effect of resiniferatoxin on the isolated rabbit iris sphincter muscle: comparison with capsaicin and bradykinin.	1992 Mar 24	1381678
Analysis of the native quaternary structure of vanilloid receptor 1.	2001 Jul 27	11358970
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.	2001 Oct	11606325
High affinity antagonists of the vanilloid receptor.	2002 Oct	12237342
Ischemic preconditioning of remote organs attenuates gastric ischemia-reperfusion injury through involvement of prostaglandins and sensory nerves.	2004 Sep 19	15363968
Inhibitory effect of PACAP-38 on acute neurogenic and non-neurogenic inflammatory processes in the rat.	2007 Sep	17698245
Preventive effect of TRPV1 agonists capsaicin and resiniferatoxin on ischemia/reperfusion-induced renal injury in rats.	2008 May	18460982
Regulation of the benzamil-insensitive salt taste receptor by intracellular Ca2+, protein kinase C, and calcineurin.	2009 Sep	19553475
Activation of TRPV1 reduces vascular lipid accumulation and attenuates atherosclerosis.	2011 Dec 1	21908651

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:32:06 GMT 2023` Edited by `admin` on `Sat Dec 16 14:32:06 GMT 2023`
Record UNII	A5O6P1UL4I
Record Status	`Validated (UNII)`
Record Version

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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