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

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
Characterisation of TRPM8 as a pharmacophore receptor.	2007 Dec	17517434
Prospects for prostate cancer imaging and therapy using high-affinity TRPM8 activators.	2007 Mar	16949669

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.

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