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AMG-333

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From Wikipedia, the free encyclopedia

Drug which acts as a potent and selective blocker of the TRPM8 ion channel

Pharmaceutical compound

AMG-333
Identifiers

IUPAC name 6-{[(S)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl}pyridine-3-carboxylic acid
CAS Number	1416799-28-4^Y
PubChemCID	71144018
ChemSpider	72380128
UNII	FR70864511
ChEMBL	ChEMBL4241349
Chemical and physical data
Formula	C₂₀H₁₂F₅N₃O₄
Molar mass	453.325 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC(=C(N=C1)[C@H](C2=CC(=C(C=C2)OC(F)(F)F)F)NC(=O)C3=NC=C(C=C3)C(=O)O)F
InChI InChI=1S/C20H12F5N3O4/c21-12-2-1-7-26-17(12)16(10-4-6-15(13(22)8-10)32-20(23,24)25)28-18(29)14-5-3-11(9-27-14)19(30)31/h1-9,16H,(H,28,29)(H,30,31)/t16-/m0/s1 Key:QEBYISWYMFIXOZ-INIZCTEOSA-N

AMG-333 is a drug which acts as a potent and selective blocker of theTRPM8 ion channel, which is the main receptor responsible for the sensation ofcold. It was developed as a potential treatment formigraine.^[1]

References

[edit]

^Horne DB, Biswas K, Brown J, Bartberger MD, Clarine J, Davis CD, et al. (September 2018). "Discovery of TRPM8 Antagonist ( S)-6-(((3-Fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)carbamoyl)nicotinic Acid (AMG 333), a Clinical Candidate for the Treatment of Migraine".Journal of Medicinal Chemistry.61 (18):8186–8201.doi:10.1021/acs.jmedchem.8b00518.PMID 30148953.S2CID 52095823.

TRP channel modulators

TRPA

Activators

4-Hydroxynonenal
4-Oxo-2-nonenal
5,6-EET
12S-HpETE
15-Deoxy-Δ^12,14-prostaglandin J2
α-Sanshool (ginger,Sichuan andmelegueta peppers)
Acrolein
Allicin (garlic)
Allyl isothiocyanate (mustard,radish,horseradish,wasabi)
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis)
Cannabidiol (cannabis)
Cannabigerol (cannabis)
Cinnamaldehyde (cinnamon)
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin)
Curcumin (turmeric)
Dehydroligustilide (celery)
Diallyl disulfide
Dicentrine (Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (ginger)
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (celery,Angelica acutiloba)
Linalool (Sichuan pepper,thyme)
Methylglyoxal
Methyl salicylate (wintergreen)
N-Methylmaleimide
Nicotine (tobacco)
Oleocanthal (olive oil)
Paclitaxel (Pacific yew)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper)
Shogaols (ginger,Sichuan andmelegueta peppers)
Tear gases
Tetrahydrocannabinol (cannabis)
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion)
Umbellulone (Umbellularia californica)
WIN 55,212-2

Blockers

TRPC

Activators	Adhyperforin (St John's wort) Diacyl glycerol GSK1702934A Hyperforin (St John's wort) Substance P
Blockers	DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-Amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators	ADP-ribose BCTC Calcium (intracellular) CIM-0216 Cold Coolact P Cooling Agent 10 Eucalyptol (eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol (mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g.,stevioside) (Stevia rebaudiana) Sweettastants (e.g.,glucose,fructose,sucrose; indirectly) Thio-BCTC WS-12
Blockers	AMG-333 Capsazepine Clotrimazole DCDPC Elismetrep Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-Amylcinnamoyl)anthranilic acid Nicotine (tobacco) Niflumic acid Ononetin PF-05105679 RQ-00203078 Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO TRPM4-IN-5