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
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
Analysis of the native quaternary structure of vanilloid receptor 1.	2001 Jul 27	11358970
High affinity antagonists of the vanilloid receptor.	2002 Oct	12237342
Effects of resiniferatoxin desensitization of capsaicin-sensitive afferents on detrusor over-activity induced by intravesical capsaicin, acetic acid or ATP in conscious rats.	2003 May	12700886
Signal transduction for inhibition of inducible nitric oxide synthase and cyclooxygenase-2 induction by capsaicin and related analogs in macrophages.	2003 Nov	14530214
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
Intravesical resiniferatoxin decreases spinal c-fos expression and increases bladder volume to reflex micturition in rats with chronic inflamed urinary bladders.	2004 Jul	15217452
Ischemic preconditioning of remote organs attenuates gastric ischemia-reperfusion injury through involvement of prostaglandins and sensory nerves.	2004 Sep 19	15363968
Evaluation of the anti-emetic potential of anti-migraine drugs to prevent resiniferatoxin-induced emesis in Suncus murinus (house musk shrew).	2005 Jan 31	15680276
Substantial role of locus coeruleus-noradrenergic activation and capsaicin-insensitive primary afferent fibers in bee venom's anti-inflammatory effect.	2006 Jun	16621078
Thermosensitive TRP ion channels mediate cytosolic calcium response in human synoviocytes.	2006 Sep	16597917
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
Effects of tolterodine on afferent neurotransmission in normal and resiniferatoxin treated conscious rats.	2007 Jul	17507042
Role of capsaicin-sensitive afferents and sensory neuropeptides in endotoxin-induced airway inflammation and consequent bronchial hyperreactivity in the mouse.	2007 Jun 7	17291600
Inhibitory effect of PACAP-38 on acute neurogenic and non-neurogenic inflammatory processes in the rat.	2007 Sep	17698245
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
Regulation of the benzamil-insensitive salt taste receptor by intracellular Ca2+, protein kinase C, and calcineurin.	2009 Sep	19553475
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:32:06 UTC 2023` Edited by `admin` on `Sat Dec 16 14:32:06 UTC 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