AF-353

AF-353
Identifiers
	IUPAC name 5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidine-2,4-diamine;
CAS Number	865305-30-2;
PubChem CID	15953802;
IUPHAR/BPS	4125;
ChemSpider	13095601;
ChEMBL	ChEMBL526307;
CompTox Dashboard ( EPA)	DTXSID90580447 ;
Chemical and physical data
Formula	C14H17IN4O2
Molar mass	400.220 g·mol−1
3D model ( JSmol)	Interactive image;
	SMILES CC(C)C1=CC(=C(C=C1OC2=CN=C(N=C2N)N)I)OC;
	InChI InChI=1S/C14H17IN4O2/c1-7(2)8-4-11(20-3)9(15)5-10(8)21-12-6-18-14(17)19-13(12)16/h4-7H,1-3H3,(H4,16,17,18,19); Key:AATPYXMXFBBKFO-UHFFFAOYSA-N;

AF-353 is a drug which acts as an antagonist of the P2X3 homotrimeric and P2X2/3 heterotrimeric forms of the P2X purinoreceptors. It has been found to block taste responses and has been proposed as an agent for masking the bitter taste of medications.^[1]^[2]^[3]

References

^ Gever JR, Soto R, Henningsen RA, Martin RS, Hackos DH, Panicker S, et al. (July 2010). "AF-353, a novel, potent and orally bioavailable P2X3/P2X2/3 receptor antagonist". British Journal of Pharmacology. 160 (6): 1387–1398. doi: 10.1111/j.1476-5381.2010.00796.x. PMC 2938810. PMID 20590629.
^ Vandenbeuch A, Larson ED, Anderson CB, Smith SA, Ford AP, Finger TE, et al. (March 2015). "Postsynaptic P2X3-containing receptors in gustatory nerve fibres mediate responses to all taste qualities in mice". The Journal of Physiology. 593 (5): 1113–1125. doi: 10.1113/jphysiol.2014.281014. PMC 4358674. PMID 25524179.
^ Flammer LJ, Ellis H, Rivers N, Caronia L, Ghidewon MY, Christensen CM, et al. (May 2024). "Topical application of a P2X2/P2X3 purine receptor inhibitor suppresses the bitter taste of medicines and other taste qualities". British Journal of Pharmacology. doi: 10.1111/bph.16411. PMID 38745397.

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[1] Gever JR, Soto R, Henningsen RA, Martin RS, Hackos DH, Panicker S, et al. (July 2010). "AF-353, a novel, potent and orally bioavailable P2X3/P2X2/3 receptor antagonist". British Journal of Pharmacology. 160 (6): 1387–1398. doi: 10.1111/j.1476-5381.2010.00796.x. PMC 2938810. PMID 20590629.

[2] Vandenbeuch A, Larson ED, Anderson CB, Smith SA, Ford AP, Finger TE, et al. (March 2015). "Postsynaptic P2X3-containing receptors in gustatory nerve fibres mediate responses to all taste qualities in mice". The Journal of Physiology. 593 (5): 1113–1125. doi: 10.1113/jphysiol.2014.281014. PMC 4358674. PMID 25524179.

[3] Flammer LJ, Ellis H, Rivers N, Caronia L, Ghidewon MY, Christensen CM, et al. (May 2024). "Topical application of a P2X2/P2X3 purine receptor inhibitor suppresses the bitter taste of medicines and other taste qualities". British Journal of Pharmacology. doi: 10.1111/bph.16411. PMID 38745397.

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Identifiers

IUPAC name 5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidine-2,4-diamine
CAS Number	865305-30-2
PubChem CID	15953802
IUPHAR/BPS	4125
ChemSpider	13095601
ChEMBL	ChEMBL526307
CompTox Dashboard ( EPA)	DTXSID90580447
Chemical and physical data
Formula	C₁₄H₁₇IN₄O₂
Molar mass	400.220 g·mol⁻¹
3D model ( JSmol)	Interactive image
SMILES CC(C)C1=CC(=C(C=C1OC2=CN=C(N=C2N)N)I)OC
InChI InChI=1S/C14H17IN4O2/c1-7(2)8-4-11(20-3)9(15)5-10(8)21-12-6-18-14(17)19-13(12)16/h4-7H,1-3H3,(H4,16,17,18,19) Key:AATPYXMXFBBKFO-UHFFFAOYSA-N