Etrasimod

Etrasimod, sold under the brand name Velsipity, is a medication that is used for the treatment of ulcerative colitis (UC).[1] It is a selective sphingosine-1-phosphate (S1P) receptor modulator that modifies the activity of the immune system.[1] It is taken by mouth.[1]

Etrasimod
Skeletal formula of etrasimod
Clinical data
Trade namesVelsipity
Other namesAPD334, APD-334
License data
Routes of
administration		By mouth
Drug classSphingosine-1-phosphate receptor modulator
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Protein binding97.9%
MetabolismLiver (CYP2C8, 2C9, 3A4)
Elimination half-life30 hours
ExcretionFeces (82%), kidneys (5%)
Identifiers
  • 2-[(3R)-7-{[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC26H26F3NO3
Molar mass457.493 g·mol−1
3D model (JSmol)
  • C1CCC(C1)C2=C(C=C(C=C2)COC3=CC4=C(C=C3)NC5=C4CC[C@@H]5CC(=O)O)C(F)(F)F
  • InChI=1S/C26H26F3NO3/c27-26(28,29)22-11-15(5-8-19(22)16-3-1-2-4-16)14-33-18-7-10-23-21(13-18)20-9-6-17(12-24(31)32)25(20)30-23/h5,7-8,10-11,13,16-17,30H,1-4,6,9,12,14H2,(H,31,32)/t17-/m1/s1
  • Key:MVGWUTBTXDYMND-QGZVFWFLSA-N

Etrasimod was discovered by Arena Pharmaceuticals, with subsequent development by Pfizer.[2]

Medical uses

Etrasimod is used for the treatment of moderate to severe ulcerative colitis.[1]

Mechanism of action

It works by causing T cells to become trapped in the lymph nodes, preventing them from entering the bloodstream, from where they would travel to other tissues in the body and mediate inflammation.[3][4][5][6][7][8]

Society and culture

Velsipity was approved by the US Food and Drug Administration (FDA) in October 2023.[1][9][10]

Names

Etrasimod is the international nonproprietary name.[11]

References
  1. Pfizer (12 October 2023). "Velsipity (etrasimod) tablets, for oral use" (PDF). U.S. Food and Drug Administration (FDA). Retrieved 18 October 2023.
  2. Bayer M (2 May 2023). "Pfizer tosses newly acquired meds out of the Arena". Fierce Biotech. Retrieved 13 October 2023.
  3. Atreya R, Neurath MF (April 2023). "The sphingosine-1-phosphate receptor agonist etrasimod in ulcerative colitis". Lancet. 401 (10383): 1132–1133. doi:10.1016/S0140-6736(23)00228-3. PMID 36871570.
  4. Sandborn WJ, Vermeire S, Peyrin-Biroulet L, Dubinsky MC, Panes J, Yarur A, et al. (April 2023). "Etrasimod as induction and maintenance therapy for ulcerative colitis (ELEVATE): two randomised, double-blind, placebo-controlled, phase 3 studies". Lancet. 401 (10383): 1159–1171. doi:10.1016/S0140-6736(23)00061-2. PMID 36871574.
  5. Dal Buono A, Gabbiadini R, Alfarone L, Solitano V, Repici A, Vetrano S, et al. (July 2022). "Sphingosine 1-Phosphate Modulation in Inflammatory Bowel Diseases: Keeping Lymphocytes Out of the Intestine". Biomedicines. 10 (7). doi:10.3390/biomedicines10071735. PMC 9313037. PMID 35885040.
  6. Argollo M, Furfaro F, Gilardi D, Roda G, Allocca M, Peyrin-Biroulet L, et al. (April 2020). "Modulation of sphingosine-1-phosphate in ulcerative colitis". Expert Opin Biol Ther. 20 (4): 413–420. doi:10.1080/14712598.2020.1732919. PMID 32093531.
  7. Al-Shamma H, Lehmann-Bruinsma K, Carroll C, Solomon M, Komori HK, Peyrin-Biroulet L, et al. (June 2019). "The Selective Sphingosine 1-Phosphate Receptor Modulator Etrasimod Regulates Lymphocyte Trafficking and Alleviates Experimental Colitis". J Pharmacol Exp Ther. 369 (3): 311–317. doi:10.1124/jpet.118.254268. PMID 30872391.
  8. Peyrin-Biroulet L, Christopher R, Behan D, Lassen C (May 2017). "Modulation of sphingosine-1-phosphate in inflammatory bowel disease". Autoimmun Rev. 16 (5): 495–503. doi:10.1016/j.autrev.2017.03.007. PMID 28279838.
  9. Brooks M (13 October 2023). "FDA Approves New Drug for Ulcerative Colitis". Medscape. Retrieved 13 October 2023.
  10. https://www.accessdata.fda.gov/drugsatfda_docs/appletter/2023/216956Orig1s000ltr.pdf
  11. World Health Organization (2017). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 78". WHO Drug Information. 31 (3). hdl:10665/330961.


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