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
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
ChEBI
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, 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 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

Legal status

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

In December 2023, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Velsipity, intended for the treatment of ulcerative colitis.[11] The applicant for this medicinal product is Pfizer Europe MA EEIG.[11]

Names

Etrasimod is the international nonproprietary name.[12]

References

  1. ^ a b c d e f 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. S2CID 257286238.
  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. S2CID 257286271.
  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): 1735. 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 Opinion on Biological Therapy. 20 (4): 413–420. doi:10.1080/14712598.2020.1732919. PMID 32093531. S2CID 211475181.
  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". The Journal of Pharmacology and Experimental Therapeutics. 369 (3): 311–317. doi:10.1124/jpet.118.254268. PMID 30872391. S2CID 78093401.
  8. ^ Peyrin-Biroulet L, Christopher R, Behan D, Lassen C (May 2017). "Modulation of sphingosine-1-phosphate in inflammatory bowel disease". Autoimmunity Reviews. 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. ^ "Velsipity (etrasimod) tablets for the treatment of moderately to severely active ulcerative colitis in adults" (PDF). Approval Letter. U.S. Food and Drug Administration.
  11. ^ a b "Velsipity EPAR". European Medicines Agency (EMA). 14 December 2023. Retrieved 17 December 2023. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  12. ^ 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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