AMG-333

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 ;
PubChem CID	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 the TRPM8 ion channel, which is the main receptor responsible for the sensation of cold. It was developed as a potential treatment for migraine.^[1]

References

^ 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 52095823.8186-8201&rft.date=2018-09&rft_id=https://api.semanticscholar.org/CorpusID:52095823#id-name=S2CID&rft_id=info:pmid/30148953&rft_id=info:doi/10.1021/acs.jmedchem.8b00518&rft.aulast=Horne&rft.aufirst=DB&rft.au=Biswas, K&rft.au=Brown, J&rft.au=Bartberger, MD&rft.au=Clarine, J&rft.au=Davis, CD&rft.au=Gore, VK&rft.au=Harried, S&rft.au=Horner, M&rft.au=Kaller, MR&rft.au=Lehto, SG&rft.au=Liu, Q&rft.au=Ma, VV&rft.au=Monenschein, H&rft.au=Nguyen, TT&rft.au=Yuan, CC&rft.au=Youngblood, BD&rft.au=Zhang, M&rft.au=Zhong, W&rft.au=Allen, JR&rft.au=Chen, JJ&rft.au=Gavva, NR&rfr_id=info:sid/en.wikipedia.org:AMG-333" class="Z3988">

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[Horne_2018-1] 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 52095823.8186-8201&rft.date=2018-09&rft_id=https://api.semanticscholar.org/CorpusID:52095823#id-name=S2CID&rft_id=info:pmid/30148953&rft_id=info:doi/10.1021/acs.jmedchem.8b00518&rft.aulast=Horne&rft.aufirst=DB&rft.au=Biswas, K&rft.au=Brown, J&rft.au=Bartberger, MD&rft.au=Clarine, J&rft.au=Davis, CD&rft.au=Gore, VK&rft.au=Harried, S&rft.au=Horner, M&rft.au=Kaller, MR&rft.au=Lehto, SG&rft.au=Liu, Q&rft.au=Ma, VV&rft.au=Monenschein, H&rft.au=Nguyen, TT&rft.au=Yuan, CC&rft.au=Youngblood, BD&rft.au=Zhang, M&rft.au=Zhong, W&rft.au=Allen, JR&rft.au=Chen, JJ&rft.au=Gavva, NR&rfr_id=info:sid/en.wikipedia.org:AMG-333" class="Z3988">

[1]

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
PubChem CID	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

See also

References