U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of Acoltremon

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
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

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/16949669

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

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

Patents

Sample Use Guides

Mouse: 10 mg/kg in a volume of 5 ml/kg
Route of Administration: Intraperitoneal
WS-12 solution (10 nM) activated SOC current followed at −100 mV in LNCaP cells.
Substance Class Chemical
Created
by admin
on Thu Jul 06 20:05:24 UTC 2023
Edited
by admin
on Thu Jul 06 20:05:24 UTC 2023
Record UNII
1L7BVT4Z4Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Acoltremon
INN  
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
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
SMS_ID
300000045594
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
JECFA MONOGRAPH
2079
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
CAS
847565-93-9
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
INN
12127
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
NCI_THESAURUS
C189962
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
CAS
1217498-35-5
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
11266244
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID10460636
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
CAS
68489-09-8
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
FDA UNII
1L7BVT4Z4Z
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
WIKIPEDIA
WS-12
Created by admin on Thu Jul 06 20:05:24 UTC 2023 , Edited by admin on Thu Jul 06 20:05:24 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
EC50
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ACTIVE MOIETY