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Key Documents

S0441

Sigma-Aldrich

SB-366791

≥98% (HPLC), powder

Synonym(s):

N-(3-Methoxyphenyl)-4-chlorocinnamide

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About This Item

Empirical Formula (Hill Notation):
C16H14NO2Cl
CAS Number:
Molecular Weight:
287.74
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

originator

GlaxoSmithKline

SMILES string

COc1cccc(NC(=O)\C=C\c2ccc(Cl)cc2)c1

InChI

1S/C16H14ClNO2/c1-20-15-4-2-3-14(11-15)18-16(19)10-7-12-5-8-13(17)9-6-12/h2-11H,1H3,(H,18,19)/b10-7+

InChI key

RYAMDQKWNKKFHD-JXMROGBWSA-N

Gene Information

human ... TRPV1(7442)

Application

SB-366791 has been used as a transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonist:
  • to infer the in vitro and in vivo pharmacology of (E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (AMG 9810)
  • to study its effects on sodium hydrogen sulfide (NaHS) or capsaicin-induced contractile activity
  • to study the inhibitory potency of phoneutria toxin (PnTx3-5) (native and recombinant) on various responses mediated by transient receptor potential cation channel subfamily V member 1 (TRPV1)

Biochem/physiol Actions

SB-366791 might exhibit analgesic properties on bone cancer-related pain behavior.
Vanilloid receptor-1 (TRPV1) antagonist.

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Y Niiyama et al.
British journal of anaesthesia, 102(2), 251-258 (2008-11-29)
Bone cancer pain has a major impact on the quality of life of cancer patients but is difficult to treat. Therefore, development of a novel strategy for bone cancer pain is needed for improvement of the patient quality of life.
Riccardo Patacchini et al.
European journal of pharmacology, 509(2-3), 171-177 (2005-03-01)
We have investigated the mechanism through which hydrogen sulfide (H2S) stimulates capsaicin-sensitive primary afferent neurons in the rat isolated urinary bladder. Sodium hydrogen sulfide (NaHS), a donor of H2S, produced concentration-dependent contractile responses (pEC50=3.5+/-0.1) that were unaffected by the transient
Elizete Maria Rita Pereira et al.
Neuropharmacology, 162, 107826-107826 (2019-10-28)
Capsaicin, an agonist of TRPV1, evokes intracellular [Ca2+] transients and glutamate release from perfused trigeminal ganglion. The spider toxin PnTx3-5, native or recombinant is more potent than the selective TRPV1 blocker SB-366791 with IC50 of 47 ± 0.18 nM, 45 ± 1.18 nM and 390 ± 5.1 nM in
Mauricio Guzmán et al.
Immunology, 161(2), 148-161 (2020-07-24)
Dry eye disease (DED) is a highly prevalent ocular surface disorder with neuroimmune pathophysiology. Tear hyperosmolarity (THO), a frequent finding in affected patients, is considered a key element in DED pathogenesis, yet existing animal models are based on subjecting the
SB366791, a TRPV1 antagonist, potentiates analgesic effects of systemic morphine in a murine model of bone cancer pain
Niiyama Y, et al.
British Journal of Anaesthesia, 102(2), 251-258 (2009)

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