Acoltremon

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H27NO2
Molecular Weight	289.4125
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(NC(=O)[C@@H]2C[C@H](C)CC[C@H]2C(C)C)C=C1

InChI

InChIKey=HNSGVPAAXJJOPQ-XOKHGSTOSA-N

InChI=1S/C18H27NO2/c1-12(2)16-10-5-13(3)11-17(16)18(20)19-14-6-8-15(21-4)9-7-14/h6-9,12-13,16-17H,5,10-11H2,1-4H3,(H,19,20)/t13-,16+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H27NO2
Molecular Weight	289.4125
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16949669
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/17517434 | https://www.ncbi.nlm.nih.gov/pubmed/23820004

WS-12 is a cooling agent and potent TRPM8 agonist. It activates TRPM8 but not related TRP channels like TRPM3 and TRPV6. WS-12 seems to activate TRPM8 mediated cation currents by shifting the voltage dependence of the activation curves to the left toward more physiological membrane potentials. Highly selective TRPM8 activators may be useful for prostate cancer imaging and/or therapy and for therapy in chronic neuropathic pain states.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Transient receptor potential cation channel subfamily M member 8 18 Target ID: CHEMBL1075319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16949669 \| https://www.ncbi.nlm.nih.gov/pubmed/17517434	Agonist 2678		39.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16949669	Primary		Basic research	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23820004	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Mouse: 10 mg/kg in a volume of 5 ml/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

WS-12 solution (10 nM) activated SOC current followed at −100 mV in LNCaP cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:30:08 GMT 2023` Edited by `admin` on `Sat Dec 16 14:30:08 GMT 2023`
Record UNII	1L7BVT4Z4Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Acoltremon

Official Name

English

(1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide

Systematic Name

English

N-(4-METHOXYPHENYL)-P-MENTHANECARBOXAMIDE

Systematic Name

English

FEMA NO. 4681

Code

English

Cyclohexanecarboxamide, N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-, [1R-(1α,2β,5α)]-

Systematic Name

English

AVX-012

Code

English

AR-15512

Code

English

acoltremon [INN]

Common Name

English

WS-12

Code

English

[1R,2S,5R]-N-(4-Methoxyphenyl)-p-menthanecarboxamide

Systematic Name

English

Cyclohexanecarboxamide, N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-

Systematic Name

English

(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

Systematic Name

English

Code System Code Type Description

CAS

57233-03-1