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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 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 Formula	C₂₆H₂₆F₃NO₃
Molecular Weight	457.5 g/mol
XLogP3	6.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	457.18647818 g/mol
Monoisotopic Mass	457.18647818 g/mol
Topological Polar Surface Area	62.3 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	695
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

API SUPPLIERS

01

Metrochem API Private Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #3A33

Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

Contact Supplier

India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

02

Dr. Reddy\'s Laboratories

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #24A41

DRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

Contact Supplier

India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF NA Not Available For Sales AUDIT

03

Egis Pharmaceuticals PLC

Hungary

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #22F114

Egis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

Contact Supplier

Hungary

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

04

Sichuan Elixir Pharmaceuticals

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Attending

Sichuan Elixir Pharmaceutical, a manufacturer of small molecule APIs & a CMO/CDMO service provider for anti-tumor characteristic APIs..

Contact Supplier

China

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

05

Curia

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Discovery on Target

Not Confirmed

06

Hebi Xinhe Pharmaceutical

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Discovery on Target

Not Confirmed

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Listed Suppliers

01

Metrochem API Private Limited

India

CPhI Worldwide, Milan

Booth #3A33

Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

Contact Supplier

India

Virtual Booth

Digital Content

Etrasimod

About the Company :

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product ...

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product groups and has been approved by ISO 9001-2015, USFDA, WHO GMP, Cofepris & Japanese authorities. Metrochem’s in-depth industry knowledge, & hi-tech & advanced infrastructure, helps it provide quality products to its customers. Note: None of the products will be supplied to the countries where this could conflict with existing patents. Further, any products under patent will be offered for R&D purposes only. However, the final responsibility lies with the buyer

02

Dr. Reddy\'s Laboratories

India

CPhI Worldwide, Milan

Booth #24A41

DRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

Contact Supplier

India

Virtual Booth

Digital Content

Etrasimod

About the Company : Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfoli...

Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfolio that provides high-quality, low-cost APIs to leading pharma companies in 80+ countries. It has 8 USFDA-inspected facilities – 6 in India & 1 each in Mexico & the UK & are inspected by international regulatory authorities on a regular basis. Its facilities are supplemented by formulation facilities that provide a wide range of dosage forms. Product(s) under patent(s) are offered only for R&D purposes U/S 107A of the Patent Act and not for commercial sale.

03

Egis Pharmaceuticals PLC

Hungary

CPhI Worldwide, Milan

Booth #22F114

Egis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

Contact Supplier

Hungary

Virtual Booth

Digital Content

Etrasimod

About the Company : Egis is a member of the Servier Group. Egis’ products are manufactured at 3 production sites in Hungary, which are certified by EMA,FDA, ANVISA, PMDA ,KFDA. Egis sells its produc...

Egis is a member of the Servier Group. Egis’ products are manufactured at 3 production sites in Hungary, which are certified by EMA,FDA, ANVISA, PMDA ,KFDA. Egis sells its products under Egis’ brand names in 18 countries. In total, the company’s APIs & finished products reach 100 countries. Egis’ focus lies on treating diseases of cardiovascular & central nervous systems; however, it also provides modern treatment solutions in the fields of diabetology, dermatology & wound care. Our research and development activities focus on high-quality, value-added branded generic products. From 2023, Egis offers its CDMO & CMO services as well.

04

Sichuan Elixir Pharmaceuticals

China

CPhI Worldwide, Milan

Attending

Sichuan Elixir Pharmaceutical, a manufacturer of small molecule APIs & a CMO/CDMO service provider for anti-tumor characteristic APIs..

Contact Supplier

China

Virtual Booth

Digital Content

Etrasimod

About the Company : Specializing in natural & oncology APIs, we establish R&D and production platforms for new salt, crystal form & synthetic biology research. We cooperate with clients for IND, NDA, ...

Specializing in natural & oncology APIs, we establish R&D and production platforms for new salt, crystal form & synthetic biology research. We cooperate with clients for IND, NDA, ANDA, 505b(2) and P-IV challenges. Exploring macromolecular APIs, we focus on Glycans & polypeptides. Expertise in XDC drugs drives innovative research & payload production. With a global registration platform & international cGMP system, we offer API CMO/CDMO services worldwide. Our strategy combines FDF and APIs. Our labs meet GMP standards with a stable R&D team, over 10 years of experience, we've delivered 20+ successful projects.

05

Curia

U.S.A

ASC 2024

Not Confirmed

06

Hebi Xinhe Pharmaceutical

China

ASC 2024

Not Confirmed

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Drugs in Development

01 Everest Medicines

U.S.A

ASC 2024

Not Confirmed

02 Everest Medicines

U.S.A

ASC 2024

Not Confirmed

03 Pfizer Inc

U.S.A

ASC 2024

Not Confirmed

04 Everest Medicines

U.S.A

ASC 2024

Not Confirmed

05 Pfizer Inc

U.S.A

ASC 2024

Not Confirmed

06 Pfizer Inc

U.S.A

ASC 2024

Not Confirmed

07 Pfizer Inc

U.S.A

ASC 2024

Not Confirmed

08 Pfizer Inc

U.S.A

ASC 2024

Not Confirmed

09 Arena

Country

ASC 2024

Not Confirmed

10 Pfizer Inc

U.S.A

ASC 2024

Not Confirmed

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DATA COMPILATION #PharmaFlow

FDA approvals rise 49% in 2023; CRISPR’s gene editing therapy sees light of day

In 2022, when the US Food and Drug Administration (FDA) was reeling under the impact of the pandemic, new drug approvals by the agency dropped by 26 percent. But last year, FDA’s new drug approvals rebounded by an impressive 49 percent, with the Center for Drug Evaluation and Research (CDER) approving 55 new drugs in 2023. Of them, 36 percent were considered first-in-class, while small molecules made up for 62 percent of the total drugs approved (i.e. 34). FDA’s Center for Biologics Evaluation and Research (CBER) okayed 19 biologics in 2023 compared to eight in the previous year.The first half of 2023 saw the debut of vaccines for the all-too-common respiratory syncytial virus (RSV). Among the other notable approvals in H1 was Biogen and Eisai’s Alzheimer’s drug Leqembi (lecanemab). Out of the total 55 drug approvals, 29 came in H2 2023. This includes Vertex Pharmaceuticals and CRISPR Therapeutics’ Casgevy that relies on the Nobel Prize-winning CRISPR gene-editing technology. Casgevy has been approved as a treatment for sickle-cell disease (SCD) and β-thalassemia.While FDA witnessed a sharp rise in approvals in 2023, many other drug regulators didn’t. The European Medicines Agency (EMA) granted marketing authorization to 32 novel drugs in 2023, a fall from 33 in 2022. Similarly, Health Canada’s approvals in 2023 decreased to 38, compared to 45 in the previous year.As usual, oncology topped the list of drug approvals by therapeutic area, at 39 (as opposed to 35 in 2022). Rare diseases was the second most popular therapeutic area for drug approvals. With drugmakers clearly paying heed to the unmet needs of patients suffering from rare diseases, this therapeutic area sprinted from a 9 percent share and the fourth position among new approvals in 2022 to an impressive 34 percent share in 2023. A quarter of the new drug approvals were in infectious diseases, followed by immunology (19 percent) and neurology (7 percent).View New Drug Approvals in 2023 with Estimated Sales (Free Excel Available) Casgevy, postpartum depression drug Zurzuvae emerge as potential blockbustersGene therapy Casgevy, postpartum depression (PPD) med Zurzuvae, blood cancer med Elrexfio and ulcerative colitis drug Velsipity were some of the prominent approvals of 2023.Britain’s Medicines and Healthcare products Regulatory Agency was the first to okay Casgevy in November as a cure for SCD and β-thalassemia. Soon, the FDA approved it for SCD. In January this year, the American agency also approved it for transfusion-dependent β-thalassemia (TDT). Analysts estimate Casgevy to generate US$ 2.6 billion in peak sales, says Nature. Biogen and Sage’s PPD therapy Zurzuvae became the first and only FDA-approved pill for the condition that can be life-threatening for both the mother and the child. Global sales of Zurzuvae are forecast to hit US$ 1.28 billion by 2028.In August, Pfizer’s Elrexfio (elranatamab) became the first “off-the-shelf” (ready-to-use) therapy in the US for multiple myeloma. The drug provides an option for patients with hard to treat or relapsed blood cancer and is estimated to bring in US$ 861 million in peak sales by 2028, says Nature.Pfizer also bagged another significant approval in October — its drug Velsipity (etrasimod) was greenlit by the FDA to treat adults with ulcerative colitis, an inflammatory bowel disease. Peak revenue for Velsipity is expected to come in at US$ 825 million, as per Evaluate.View New Drug Approvals in 2023 with Estimated Sales (Free Excel Available) Astra’s Truqap, GSK’s Ojjaara among top cancer therapies given FDA nod in H2In November, FDA approved AstraZeneca’s Truqap (capivasertib) in combination with the Anglo-Swedish drugmaker’s Faslodex (fulvestrant) for treating adult patients with hormone receptor (HR)-positive, HER2-negative locally advanced or metastatic breast cancer with one or more biomarker alterations. Evaluate Pharma forecasts peak Truqap sales to come in at about US$ 690 million.In September, FDA approved GSK’s Ojjaara (momelotinib) as the first and only treatment for myelofibrosis with anemia. Nearly all myelofibrosis patients are estimated to develop anemia over the course of the disease. Ojjaara is taken orally once a day.Other notable oncology treatments okayed by FDA in H2 2023 include Daiichi’s Vanflyta (quizartinib) in July to treat an aggressive blood cancer known as acute myeloid leukemia (AML). In August, FDA approved Janssen’s bispecific antibody Talvey (talquetamab-tgvs) for difficult-to-treat blood cancer. The agency approved two cancer therapies in November — BMS’ Augtyro (repotrectinib) for ROS1-positive non-small cell lung cancer (NSCLC) and Takeda’s targeted oral therapy Fruzaqla (fruquintinib) for adult patients with metastatic colorectal cancer (mCRC).View New Drug Approvals in 2023 with Estimated Sales (Free Excel Available) Rare disease drugs Santhera-Catalyst’s Agamree, Novo’s Rivfloza bag approval in H2In October, FDA approved Santhera Pharmaceuticals and Catalyst Pharma’s Agamree (vamorolone), an oral suspension treatment for Duchenne muscular dystrophy (DMD) in patients two years of age and older. This makes it the first drug fully approved in both the US and Europe for the muscle degeneration disorder. Agamree acts in a manner similar to other steroids, which are the standard of care for the inherited rare disease. However, it causes fewer side effects.FDA also okayed Novo Nordisk’s once-a-month injection Rivfloza (nedosiran) in October to treat a rare genetic condition — primary hyperoxaluria type 1 (PH1) — that causes recurring kidney stones.In November, the agency approved Takeda’s Adzynma (ADAMTS13, recombinant-krhn) as the first treatment for both adult and pediatric patients with congenital thrombotic thrombocytopenic purpura (cTTP), a rare genetic blood disorder. Other noteworthy FDA approvals in H2 2023 for rare blood diseases include Novartis’ Fabhalta and bluebird bio's Lyfgenia. Fabhalta is the first oral monotherapy for the treatment of adults with paroxysmal nocturnal hemoglobinuria, a rare disease that causes symptoms such as hemolytic anemia, hemoglobinuria (excretion of hemoglobin in the urine), fatigue, shortness of breath etc. Lyfgenia is the first cell-based gene therapy for the treatment of SCD in patients 12 years and older. Similarly, another rare disease drug — Regeneron’s Veopoz — bagged FDA approval in August last. Veopoz treats CHAPLE disease, an ultra-rare disease in which patients have severe gastrointestinal problems.View New Drug Approvals in 2023 with Estimated Sales (Free Excel Available) Our viewAfter a lull in 2022, new drug approvals have finally gathered momentum. The good news is that this year, several pathbreaking drugs are coming up for approval, such as Madrigal Pharmaceuticals’ resmetirom (the first treatment for NASH with liver fibrosis), Merck’s sotatercept (a treatment for pulmonary arterial hypertension), Lilly’s donanemab for Alzheimer’s disease and Karuna Therapeutics’ drug to treat schizophrenia. Let’s hope 2024 turns out to be an even bigger year for new drug approvals.

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ABOUT THIS PAGE

Finished Dosage Form (FDF) import of Etrasimod obtained from Indian Custom Trade Statistics

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Discover Molecule Insights

ACTIVE PHARMA INGREDIENTS

6 API Suppliers

6 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

22 Drugs in Development

FINISHED DOSAGE FORMULATIONS

1 FDF Dossiers

1 Europe

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow

1 STOCK RECAP #PipelineProspector

25 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 Finished Drug Prices

MARKET PLACE

2 APIs

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 6

MARKET PLACE

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

PATENTS & EXCLUSIVITIES

DIGITAL CONTENT

GLOBAL SALES INFORMATION

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