BAY-59-3074

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H13F6NO4S
Molecular Weight	453.356
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)CCCS(=O)(=O)OC1=CC=CC(OC2=CC=CC(=C2C#N)C(F)(F)F)=C1

InChI

InChIKey=LWUSZIVDPJPVBW-UHFFFAOYSA-N

InChI=1S/C18H13F6NO4S/c19-17(20,21)8-3-9-30(26,27)29-13-5-1-4-12(10-13)28-16-7-2-6-15(14(16)11-25)18(22,23)24/h1-2,4-7,10H,3,8-9H2

HIDE SMILES / InChI

Molecular Formula	C18H13F6NO4S
Molecular Weight	453.356
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15140913 | https://www.ncbi.nlm.nih.gov/pubmed/15556145

BAY-59-3074 is a novel, selective cannabinoid CB(1)/CB(2) receptor ligand (K(i) = 55.4, 48.3, and 45.5 nM at rat and human cannabinoid CB(1) and human CB(2) receptors, respectively), with partial agonist properties at these receptors in guanosine 5-[gamma(35)S]-thiophosphate triethyl-ammonium salt ([(35)S]GTPgammaS) binding assays. It displays anti-hyperalgesic and antiallodynic properties in rat models of chronic neuropathic and inflammatory pain. BAY-59-3074 may offer a valuable therapeutic approach to treat diverse chronic pain conditions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15140913	Partial Agonist 290		45.5 nM [Ki]
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15140913	Partial Agonist 290		48.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15140913 https://www.ncbi.nlm.nih.gov/pubmed/15556145	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
3-[2-cyano-3-(trifluoromethyl)phenoxy]phenyl-4,4,4-trifluoro-1-butanesulfonate (BAY 59-3074): a novel cannabinoid Cb1/Cb2 receptor partial agonist with antihyperalgesic and antiallodynic effects.	2004 Aug	15140913
Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat.	2004 Nov 28	15556145
Conformationally constrained analogs of BAY 59-3074 as novel cannabinoid receptor ligands.	2011 Oct 1	21880487

Patents

Sample Use Guides

In Vivo Use Guide

Rats: BAY-59-3074 (0.3-3 mg/kg, p.o.) induced antihyperalgesic and antiallodynic effects against thermal or mechanical stimuli in rat models of chronic neuropathic (chronic constriction injury, spared nerve injury, tibial nerve injury, and spinal nerve ligation models) and inflammatory pain (carrageenan and complete Freund's adjuvant models).

Route of Administration: Oral

In Vitro Use Guide

EC50 value at rat brain membranes was 122.7+/- 20.9 nM, at human cortex membranes was 142.7+/-11.6 nM, on recombinant cannabinoid CB2 receptors, EC50 value was 15.8+/- 8.0 nM for BAY 59-3074.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:44:18 UTC 2023` Edited by `admin` on `Sat Dec 16 09:44:18 UTC 2023`
Record UNII	5FO5Z101GU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BAY-59-3074

Common Name

English

1-BUTANESULFONIC ACID, 4,4,4-TRIFLUORO-, 3-(2-CYANO-3-(TRIFLUOROMETHYL)PHENOXY)PHENYL ESTER

Systematic Name

English

BAY-593074

Systematic Name

English

Code System Code Type Description

CAS

406205-74-1