Izencitinib

Izencitinib
Identifiers
	IUPAC name 3-[(1R,5S)-3-[[7-[(5-methyl-1H-pyrazol-3-yl)amino]-1,6-naphthyridin-5-yl]amino]-8-azabicyclo[3.2.1]octan-8-yl]propanenitrile;
CAS Number	2051918-33-1;
PubChem CID	124090478;
IUPHAR/BPS	10458;
DrugBank	DB16660;
ChemSpider	75536963;
UNII	2ZT81PV5UM;
ChEMBL	ChEMBL4650343;
Chemical and physical data
Formula	C22H26N8
Molar mass	402.506 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=NN1)NC2=NC(=C3C=CC=NC3=C2)NC4C[C@H]5CC[C@@H](C4)N5CCC#N;
	InChI InChI=1S/C22H26N8/c1-14-10-21(29-28-14)26-20-13-19-18(4-2-8-24-19)22(27-20)25-15-11-16-5-6-17(12-15)30(16)9-3-7-23/h2,4,8,10,13,15-17H,3,5-6,9,11-12H2,1H3,(H3,25,26,27,28,29)/t15?,16-,17+; Key:DADAEARVGOQWHV-ALOPSCKCSA-N;

Izencitinib (TD-1473) is a drug which acts as a pan-Janus kinase inhibitor, binding with high affinity at all three subtypes JAK1, JAK2 and JAK3. It is taken orally and was developed to be gut selective with minimal absorption into the rest of the body, allowing targeting of inflammatory bowel disease but with reduced side effects compared to other similar drugs.^[1]^[2]

References

^ Roda G, Dal Buono A, Argollo M, Danese S (September 2020). "JAK selectivity: more precision less troubles". Expert Review of Gastroenterology & Hepatology. 14 (9): 789–796. doi:10.1080/17474124.2020.1780120. PMID 32520647.
^ Hardwick RN, Brassil P, Badagnani I, Perkins K, Obedencio GP, Kim AS, et al. (March 2022). "Gut-Selective Design of Orally Administered Izencitinib (TD-1473) Limits Systemic Exposure and Effects of Janus Kinase Inhibition in Nonclinical Species". Toxicological Sciences. 186 (2): 323–337. doi:10.1093/toxsci/kfac002. PMC 8963331. PMID 35134999.

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[1] Roda G, Dal Buono A, Argollo M, Danese S (September 2020). "JAK selectivity: more precision less troubles". Expert Review of Gastroenterology & Hepatology. 14 (9): 789–796. doi:10.1080/17474124.2020.1780120. PMID 32520647.

[2] Hardwick RN, Brassil P, Badagnani I, Perkins K, Obedencio GP, Kim AS, et al. (March 2022). "Gut-Selective Design of Orally Administered Izencitinib (TD-1473) Limits Systemic Exposure and Effects of Janus Kinase Inhibition in Nonclinical Species". Toxicological Sciences. 186 (2): 323–337. doi:10.1093/toxsci/kfac002. PMC 8963331. PMID 35134999.

[1]

[2]

Identifiers

IUPAC name 3-[(1R,5S)-3-[[7-[(5-methyl-1H-pyrazol-3-yl)amino]-1,6-naphthyridin-5-yl]amino]-8-azabicyclo[3.2.1]octan-8-yl]propanenitrile
CAS Number	2051918-33-1
PubChem CID	124090478
IUPHAR/BPS	10458
DrugBank	DB16660
ChemSpider	75536963
UNII	2ZT81PV5UM
ChEMBL	ChEMBL4650343
Chemical and physical data
Formula	C₂₂H₂₆N₈
Molar mass	402.506 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=CC(=NN1)NC2=NC(=C3C=CC=NC3=C2)NC4C[C@H]5CC[C@@H](C4)N5CCC#N
InChI InChI=1S/C22H26N8/c1-14-10-21(29-28-14)26-20-13-19-18(4-2-8-24-19)22(27-20)25-15-11-16-5-6-17(12-15)30(16)9-3-7-23/h2,4,8,10,13,15-17H,3,5-6,9,11-12H2,1H3,(H3,25,26,27,28,29)/t15?,16-,17+ Key:DADAEARVGOQWHV-ALOPSCKCSA-N

Izencitinib

See also

References