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Chemistry

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Also known as: 1206123-37-6, Apd334, Apd-334, Etrasimod [usan], 6wh8495mmh, Apd-334(free acid)
Molecular Formula
C26H26F3NO3
Molecular Weight
457.5  g/mol
InChI Key
MVGWUTBTXDYMND-QGZVFWFLSA-N
FDA UNII
6WH8495MMH

Etrasimod
Etrasimod is under investigation in clinical trial NCT03945188 (Etrasimod Versus Placebo for the Treatment of Moderately to Severely Active Ulcerative Colitis).
1 2D Structure

Etrasimod

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(3R)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid
2.1.2 InChI
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
2.1.3 InChI Key
MVGWUTBTXDYMND-QGZVFWFLSA-N
2.1.4 Canonical SMILES
C1CCC(C1)C2=C(C=C(C=C2)COC3=CC4=C(C=C3)NC5=C4CCC5CC(=O)O)C(F)(F)F
2.1.5 Isomeric SMILES
C1CCC(C1)C2=C(C=C(C=C2)COC3=CC4=C(C=C3)NC5=C4CC[C@@H]5CC(=O)O)C(F)(F)F
2.2 Other Identifiers
2.2.1 UNII
6WH8495MMH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (r)-2-(7-((4-cyclo-pentyl-3-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydro-cyclopenta(b)indol-3-yl)acetic Acid)

2.3.2 Depositor-Supplied Synonyms

1. 1206123-37-6

2. Apd334

3. Apd-334

4. Etrasimod [usan]

5. 6wh8495mmh

6. Apd-334(free Acid)

7. Chembl3358920

8. Etrasimod (usan)

9. 1206123-37-6 (free Base)

10. (r)-2-(7-((4-cyclopentyl-3-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid

11. (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl) Acetic Acid

12. 2-[(3r)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic Acid

13. Etrasimod(apd334)

14. Etrasimod [inn]

15. Etrasimod [who-dd]

16. Unii-6wh8495mmh

17. Apd334apd334

18. Gtpl9331

19. Schembl1919311

20. Bcp19558

21. Ex-a1633

22. Bdbm50041691

23. Akos032944972

24. Zinc117522788

25. Apd334-003

26. Compound 4 [pmid: 25516790]

27. Cs-6181

28. Db14766

29. Ac-35444

30. Hy-12789

31. D10930

32. F10118

33. Q27265630

34. ((3r)-7-((4-cyclopentyl-3-(trifluoromethyl)phenyl)methoxy)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic Acid

35. (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid

36. Cyclopent(b)indole-3-acetic Acid, 7-((4-cyclopentyl-3-(trifluoromethyl)phenyl)methoxy)-1,2,3,4-tetrahydro-, (3r)-

2.4 Create Date
2010-03-01
3 Chemical and Physical Properties
Molecular Weight 457.5 g/mol
Molecular Formula C26H26F3NO3
XLogP36.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass457.18647818 g/mol
Monoisotopic Mass457.18647818 g/mol
Topological Polar Surface Area62.3 Ų
Heavy Atom Count33
Formal Charge0
Complexity695
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

API SUPPLIERS

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Drugs in Development

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Details:

Abivax is actively conducting preclinical studies ABX-464 (obefazimod) in combination with Etrasimod for treating Inflammatory Bowel Disease (IBD) in the Mouse Model.


Lead Product(s): Obefazimod,Etrasimod

Therapeutic Area: Gastroenterology Brand Name: ABX-464

Study Phase: PreclinicalProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable September 25, 2024

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01

Abivax

France
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Antibody Engineering
Not Confirmed

Abivax

France
arrow
Antibody Engineering
Not Confirmed

Details : Abivax is actively conducting preclinical studies ABX-464 (obefazimod) in combination with Etrasimod for treating Inflammatory Bowel Disease (IBD) in the Mouse Model.

Brand Name : ABX-464

Molecule Type : Small molecule

Upfront Cash : Not Applicable

September 25, 2024

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Details:

Velsipity (etrasimod) is an FDA-approved oral S1P receptor modulator, with its NDA accepted in Macau for adults with moderately to severely active ulcerative colitis.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: Velsipity

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 10, 2024

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02

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Velsipity (etrasimod) is an FDA-approved oral S1P receptor modulator, with its NDA accepted in Macau for adults with moderately to severely active ulcerative colitis.

Brand Name : Velsipity

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 10, 2024

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Details:

Velsipity (etrasimod) is a once-daily, oral, sphingosine 1-phosphate (S1P) receptor modulator that selectively binds with S1P receptor subtypes 1, 4, and 5. It is approved for the treatment of patients with moderately to severely active ulcerative colitis.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: Velsipity

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable November 30, 2023

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03

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Velsipity (etrasimod) is a once-daily, oral, sphingosine 1-phosphate (S1P) receptor modulator that selectively binds with S1P receptor subtypes 1, 4, and 5. It is approved for the treatment of patients with moderately to severely active ulcerative coliti...

Brand Name : Velsipity

Molecule Type : Small molecule

Upfront Cash : Not Applicable

November 30, 2023

blank

Details:

Velsipity (etrasimod), an oral, once-daily, selective sphingosine-1-phosphate (S1P) receptor modulator, is approved by the FDA for adults with moderately to severely active ulcerative colitis (UC).


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: Velsipity

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable October 13, 2023

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04

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Details : Velsipity (etrasimod), an oral, once-daily, selective sphingosine-1-phosphate (S1P) receptor modulator, is approved by the FDA for adults with moderately to severely active ulcerative colitis (UC).

Brand Name : Velsipity

Molecule Type : Small molecule

Upfront Cash : Not Applicable

October 13, 2023

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Details:

APD334 (etrasimod) is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5. It is being investigated for the treatment of moderate-severe active ulcerative colitis.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: APD334

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Pfizer Inc

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 17, 2023

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05

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : APD334 (etrasimod) is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5. It is being investigated for the treatment of moderate-severe active ul...

Brand Name : APD334

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 17, 2023

blank

Details:

Etrasimod is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5. In addition to UC, it is being investigated for a range of other immuno-inflammatory diseases.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: APD334

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Everest Medicines

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable December 21, 2022

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06

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Details : Etrasimod is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5. In addition to UC, it is being investigated for a range of other immuno-inflamma...

Brand Name : APD334

Molecule Type : Small molecule

Upfront Cash : Not Applicable

December 21, 2022

blank

Details:

APD334 (Etrasimod) is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: APD334

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 24, 2022

blank

07

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Details : APD334 (Etrasimod) is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5.

Brand Name : APD334

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 24, 2022

blank

Details:

Etrasimod is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: APD334

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Pfizer Inc

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 29, 2022

blank

08

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Details : Etrasimod is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator designed for optimized pharmacology and engagement of S1P receptors 1, 4, and 5.

Brand Name : APD334

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 29, 2022

blank

Details:

Etrasimod is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator being investigated for a range of immuno-inflammatory diseases including ulcerative colitis, Crohn’s Disease, atopic dermatitis, eosinophilic esophagitis, and alopecia areata.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: APD334

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 23, 2022

blank

09

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Pfizer Inc

U.S.A
arrow
Antibody Engineering
Not Confirmed

Details : Etrasimod is an oral, once-a-day, selective sphingosine 1-phosphate (S1P) receptor modulator being investigated for a range of immuno-inflammatory diseases including ulcerative colitis, Crohn’s Disease, atopic dermatitis, eosinophilic esophagitis, and ...

Brand Name : APD334

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 23, 2022

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  • Deals

Details:

Arena Pharmaceuticals brings to Pfizer a portfolio of diverse and promising development-stage therapeutic candidates in gastroenterology, dermatology, and cardiology, including etrasimod, an oral, selective sphingosine 1-phosphate (S1P) receptor modulator.


Lead Product(s): Etrasimod

Therapeutic Area: Gastroenterology Brand Name: APD334

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Pfizer Inc

Deal Size: $6,700.0 million Upfront Cash: $6,700.0 million

Deal Type: Acquisition March 11, 2022

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10

Arena

Country
arrow
Antibody Engineering
Not Confirmed

Arena

Country
arrow
Antibody Engineering
Not Confirmed

Details : Arena Pharmaceuticals brings to Pfizer a portfolio of diverse and promising development-stage therapeutic candidates in gastroenterology, dermatology, and cardiology, including etrasimod, an oral, selective sphingosine 1-phosphate (S1P) receptor modulato...

Brand Name : APD334

Molecule Type : Small molecule

Upfront Cash : $6,700.0 million

March 11, 2022

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Brand Name : Wellsipity

U.S.A
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Not Confirmed

Brand Name : Wellsipity

U.S.A
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Antibody Engineering
Not Confirmed

Etrasimod

Dosage Form : Tablet, film-coated

Dosage Strength : 2 mg

Price Per Pack (Euro) : 1,001.09

Published in :

Country : Norway

RX/OTC/DISCN :

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