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16 US Patents, 5 US Exclusivities

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Moehs Relugolix

Synopsis

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Chemistry

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Also known as: 737789-87-6, Tak-385, Orgovyx, Tak 385, 1-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-3-methoxyurea, Chembl1800159

Molecular Formula

C₂₉H₂₇F₂N₇O₅S

Molecular Weight

623.6 g/mol

InChI Key

AOMXMOCNKJTRQP-UHFFFAOYSA-N

FDA UNII

P76B05O5V6

Relugolix is an orally available, non-peptide gonadotropin-releasing hormone (GnRH or luteinizing hormone-releasing hormone (LHRH)) antagonist, with potential antineoplastic activity. Relugolix competitively binds to and blocks the GnRH receptor in the anterior pituitary gland, which both prevents GnRH binding to the GnRH receptor and inhibits the secretion and release of both luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone from Leydig cells in the testes. Since testosterone is required to sustain prostate growth, reducing testosterone levels may inhibit hormone-dependent prostate cancer cell proliferation.

Relugolix is a Gonadotropin Releasing Hormone Receptor Antagonist. The mechanism of action of relugolix is as a Gonadotropin Releasing Hormone Receptor Antagonist, and Cytochrome P450 3A Inducer, and Cytochrome P450 2B6 Inducer, and Breast Cancer Resistance Protein Inhibitor, and P-Glycoprotein Inhibitor. The physiologic effect of relugolix is by means of Decreased GnRH Secretion.

1 2D Structure

Relugolix

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea

2.1.2 InChI

InChI=1S/C29H27F2N7O5S/c1-36(2)14-19-24-26(39)38(22-12-13-23(42-3)34-33-22)29(41)37(15-18-20(30)6-5-7-21(18)31)27(24)44-25(19)16-8-10-17(11-9-16)32-28(40)35-43-4/h5-13H,14-15H2,1-4H3,(H2,32,35,40)

2.1.3 InChI Key

AOMXMOCNKJTRQP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CC1=C(SC2=C1C(=O)N(C(=O)N2CC3=C(C=CC=C3F)F)C4=NN=C(C=C4)OC)C5=CC=C(C=C5)NC(=O)NOC

2.2 Other Identifiers

2.2.1 UNII

P76B05O5V6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno(2,3-d)pyrimidin-6-yl)phenyl)-3-methoxyurea

2. Orgovyx

3. Tak 385

4. Tak-385

5. Tak385

2.3.2 Depositor-Supplied Synonyms

1. 737789-87-6

2. Tak-385

3. Orgovyx

4. Tak 385

5. 1-(4-(1-(2,6-difluorobenzyl)-5-((dimethylamino)methyl)-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-3-methoxyurea

6. Chembl1800159

7. P76b05o5v6

8. 1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea

9. Urea, N-(4-(1-((2,6-difluorophenyl)methyl)-5-((dimethylamino)methyl)-1,2,3,4-tetrahydro-3-(6-methoxy-3-pyridazinyl)-2,4-dioxothieno(2,3-d)pyrimidin-6-yl)phenyl)-n'-methoxy-

10. Relugolix [usan:inn]

11. Unii-p76b05o5v6

12. Tak385

13. Tak-385/tak385

14. Relugolix (jan/inn)

15. Relugolix [inn]

16. Relugolix [jan]

17. Relugolix(tak-385)

18. Relugolix [usan]

19. Relugolix [who-dd]

20. Schembl778416

21. Gtpl5586

22. Relugolix [orange Book]

23. C29h27f2n7o5s

24. Dtxsid40224167

25. Rvt-601

26. Amy27916

27. Bcp21587

28. Ex-a1083

29. Myfembree Component Relugolix

30. Tak-385; Rvt-601

31. Bdbm50347982

32. Mfcd25976856

33. S5808

34. Zinc43206033

35. Cs-5917

36. Db11853

37. Relugolix Component Of Myfembree

38. Sb16721

39. Ac-35863

40. Bs-18032

41. Hy-16474

42. N-(4-(1-((2,6-difluorophenyl)methyl)-5-((dimethylamino)methyl)-1,2,3,4-tetrahydro-3-(6-methoxy-3-pyridazinyl)-2,4-dioxothieno(2,3-d)pyrimidin-6-yl)phenyl)-n'-methoxyurea

43. D10888

44. A857822

45. Ryeqo (relugolix-estradiol-norethisterone Acetate)

46. Q21099000

47. 1-(4-(1-((2,6-difluorophenyl)methyl)-5-((dimethylamino)methyl)-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno(2,3-d)pyrimidin-6-yl)phenyl)-3-methoxyurea

48. 1-[4-[1-[(2,6-difluorophenyl)methyl]-5-(dimethylaminomethyl)-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[4,5-e]pyrimidin-6-yl]phenyl]-3-methoxyurea

49. 1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea;relugolix

50. 1-{4-[1-(2,6-difluorobenzyl)-5-dimethylaminomethyl-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₂₇F₂N₇O₅S
Molecular Weight	623.6 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	623.17624448 g/mol
Monoisotopic Mass	623.17624448 g/mol
Topological Polar Surface Area	158 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	1010
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Relugolix is indicated for the treatment of adult patients with advanced prostate cancer. In a combination product with [estradiol] and [norethindrone], relugolix is indicated for the once-daily treatment for the management of heavy menstrual bleeding associated with uterine fibroids in premenopausal women.

Orgovyx is indicated for the treatment of adult patients with advanced hormone-sensitive prostate cancer .

5 Pharmacology and Biochemistry

5.1 Pharmacology

Approximately 56% of patients achieved castrate-level testosterone concentrations (<50 ng/dL) by day 4 of therapy and 97% of patients maintain these levels through 48 weeks of therapy. Relugolix requires once-daily oral administration to maintain the desired testosterone concentrations. Androgen deprivation therapies may prolong the QTc interval and should therefore be used with caution in patients having a high baseline risk of QTc prolongation, such as those with electrolyte abnormalities, congestive heart failure, or using other medications known to prolong the QTc interval. Based on its mechanism of action and data from animal studies, relugolix may result in fetal harm if administered to pregnant females - male patients with female partners should be advised to use effective contraception throughout therapy and for 2 weeks following cessation of therapy to prevent inadvertent fetal exposure.

5.2 MeSH Pharmacological Classification

Androgen Antagonists

Compounds which inhibit or antagonize the biosynthesis or actions of androgens. (See all compounds classified as Androgen Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

RELUGOLIX

5.3.2 FDA UNII

P76B05O5V6

5.3.3 Pharmacological Classes

Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Decreased GnRH Secretion [PE]; Gonadotropin Releasing Hormone Receptor Antagonist [EPC]; Gonadotropin Releasing Hormone Receptor Antagonists [MoA]; P-Glycoprotein Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]

5.4 ATC Code

L02BX

L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BX - Other hormone antagonists and related agents

L02BX04 - Relugolix

5.5 Absorption, Distribution and Excretion

Absorption

The C_max and AUC of orally-administered relugolix increase proportionally following single doses - in contrast, with repeat dosing the AUC remains proportional to the dose while the C_max increases greater than proportionally to the dose. Following the administration of 120mg once daily, the steady-state AUC and C_max of relugolix were 407 ( 168) ng.hr/mL and 70 ( 65) ng/mL, respectively. The absolute oral bioavailability of relugolix is approximately 12% and the median T_max following oral administration is 2.25 hours.

Route of Elimination

Approximately 81% of an orally administered dose was recovered in the feces, of which 4.2% was unchanged parent drug, while 4.1% of the dose was recovered in the urine, of which 2.2% remained unchanged.

Clearance

The average renal clearance of relugolix is 8 L/h with a total clearance of 26.4 L/h.

5.6 Metabolism/Metabolites

Relugolix is metabolized mainly by the CYP3A subfamily of P450 enzymes, with a smaller contribution by CYP2C8.

5.7 Biological Half-Life

The average effective half-life of relugolix is 25 hours, while the average terminal elimination half-life is 60.8 hours.

5.8 Mechanism of Action

The pathogenesis and progression of prostate cancer appear driven, at least in part, by the effects of testosterone. Androgen deprivation has been demonstrated to result in cell death and tumor regression in many well-differentiated prostate cancer cell lines - for this reason, androgen deprivation therapy (ADT) has become a standard in the treatment of prostate cancer, particularly in advanced disease. Testosterone production in males is carried out in the Leydig cells of testes and is stimulated by luteinizing hormone (LH), which itself is produced in the pituitary gland following the binding of gonadotropin-releasing hormone (GnRH) to corresponding GnRH receptors. Relugolix is a competitive antagonist of these GnRH receptors, thereby decreasing the release of LH and, ultimately, testosterone.

API SUPPLIERS

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USDMF

01

Moehs Iberica Sl

Spain

CPhI WW Frankfurt

Booth #11.0C6

Moehs Group, a reference company in the production of pharmaceutical active ingredients.

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Spain

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Digital Content

Relugolix

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 37795

Submission : 2022-12-23

Status : Active

Type : II

02

Dr Reddys Laboratories Ltd

India

CPhI India 2024

Booth #RH.E02

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

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India

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Digital Content

Relugolix

GDUFA

DMF Review : Complete

Rev. Date : 2024-08-05

Pay. Date : 2024-07-10

DMF Number : 39507

Submission : 2024-03-20

Status : Active

Type : II

03

Porton Pharma Solutions Ltd

China

American Pharma Summit

Not Confirmed

Porton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

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China

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Relugolix

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 39995

Submission : 2024-06-14

Status : Active

Type : II

04

Aurisco Pharmaceutical Co Ltd

China

American Pharma Summit

Not Confirmed

05

Bdr Lifesciences Private Ltd

India

American Pharma Summit

Not Confirmed

06

Beijing Hope Pharmaceutical Co Ltd

China

American Pharma Summit

Not Confirmed

07

Changzhou Pharmaceutical Factory

China

American Pharma Summit

Not Confirmed

08

Cipla Ltd

India

American Pharma Summit

Not Confirmed

09

Intas Pharmaceuticals Ltd

India

American Pharma Summit

Not Confirmed

10

Lee Pharma Ltd

India

American Pharma Summit

Not Confirmed

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Excella GmbH & Co. KG

Luxembourg

BOS Manchester

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Fareva is a one-stop-shop for API/HPAPI, OSD & Sterile products, is USFDA, EMA and PMDA-inspected and has multiple NDA & ANDA filings.

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Luxembourg

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RELUGOLIX

NDC Package Code : 46014-1130

Start Marketing Date : 2020-12-18

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT FOR HUMAN P...

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Medichem S.A.

Spain

CPhI India 2024

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Spain

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RELUGOLIX

NDC Package Code : 53296-0131

Start Marketing Date : 2024-08-02

End Marketing Date : 2025-12-31

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Marketing Category : BULK INGREDIENT

03

BDR Lifesciences Private Limited

India

euroPLX 86 Munich

Not Confirmed

04

Hetero Labs Limited

India

euroPLX 86 Munich

Not Confirmed

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Listed Suppliers

01

Moehs Iberica

Spain

CPhI WW Frankfurt

Booth #11.0C6

Moehs Group, a reference company in the production of pharmaceutical active ingredients.

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Spain

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Relugolix

About the Company : Since its founding in 1962, MOEHS has produced Active Pharmaceutical Ingredients (APIs) for the international pharmaceutical industry. Thanks to a business history of more than 50 ...

Since its founding in 1962, MOEHS has produced Active Pharmaceutical Ingredients (APIs) for the international pharmaceutical industry. Thanks to a business history of more than 50 years, MOEHS has considerable technical experience in the production of these substances. At Moehs Group we have a large tradition and experience in the area of manufacturing of active pharmaceutical and veterinary ingredients, agrochemicals, nutraceutical, cosmetic, as well as fine chemistry in general, with high levels of quality and safety standards-GMP´s, ICH, approved by the FDA and TGA.

02

Metrochem API Private Limited

India

Pharmtech & Ingredients

Exhibiting

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

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India

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Relugolix

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

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Aspen API

Netherlands

CPhI India 2024

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Aspen API. More than just an API.

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Relugolix

About the Company : Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen...

Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen API works tirelessly to deliver top-quality APIs to clients worldwide. Aspen API has a portfolio of over 58 high-quality APIs, including high potency, oncology, peptides, narcotics, analgesics, botanical extractions, and biochemicals. Aspen API places a strong emphasis on sustainability. It employs eco-friendly technologies and solvents in its chemical processes, ensuring responsible and environmentally conscious manufacturing.

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Dr. Reddy's Laboratories

India

CPhI India 2024

Booth #RH.E02

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

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India

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Relugolix

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

05

Aptra Synthesis

India

CPhI India 2024

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India

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Relugolix

About the Company : Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilities that adhere to G...

Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilities that adhere to GMP standards. We take great pride in producing top-notch intermediates through our fully backward-integrated process. Aptra Synthesis Private Limited (ASPL) stands as one of the rapidly emerging manufacturers of Active Pharmaceutical Ingredients (APIs), Pellets (Semi-finished Formulations), and Intermediates.

06

Hubei Gedian Humanwell Pharmaceutic...

China

CPhI India 2024

Attending

Hubei Gedian Humanwell focuses on R&D, production, & sales of fertility regulation drugs & steroidal APIs.

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China

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Relugolix

About the Company : Hubei Gedian Humanwell Pharmaceutical Co., Ltd. is a modern high-tech pharmaceutical company with a focus on the research and development, production, and sales of fertility regula...

Hubei Gedian Humanwell Pharmaceutical Co., Ltd. is a modern high-tech pharmaceutical company with a focus on the research and development, production, and sales of fertility regulation drugs and steroidal APIs. It operates as a wholly-owned subsidiary of Humanwell Healthcare Group (Stock Code: 600079), one of the leading pharmaceutical conglomerates in China. The company operates two APIs manufacturing sites, one formulation factory, and one excipients factory, showcasing its commitment to integrating the reproductive health industry chain from raw materials and active pharmaceutical ingredients (APIs) to finished dosage forms.

07

Medichem S.A

Spain

CPhI India 2024

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Relugolix

About the Company : Medichem is an indepently-owned company based in Barcelona. Founded in 1972 and with more than 45 years, Medichem has been engaged in the process development and manufacture of Act...

Medichem is an indepently-owned company based in Barcelona. Founded in 1972 and with more than 45 years, Medichem has been engaged in the process development and manufacture of Active Pharmaceutical Ingredients (APIs), including Highly Potent. In 2016, Medichem merged with Combino Pharm, which is devoted to the development and manufacture (licensing) of Finished Dosage Forms. With this merger, Medichem has become a vertically integrated pharmaceutical company which can offer a complete range of products and services for the pharmaceutical industry with the highest standards of quality, operational excellence and environment respect.

08

Shandong Loncom Pharmaceutical

China

BioFlorida Conference

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Shandong Loncom is an R&D-focused manufacturer of Anti-cancer APIs.

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China

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Relugolix

About the Company : Established in May 2012, Shandong Loncom Pharmaceutical operates as a fully owned subsidiary of Shandong Bestcomm Pharmaceutical Co., Ltd. Situated in the Qihe Economic Development...

Established in May 2012, Shandong Loncom Pharmaceutical operates as a fully owned subsidiary of Shandong Bestcomm Pharmaceutical Co., Ltd. Situated in the Qihe Economic Development Zone, Shandong Province, Shandong Loncom has operational API pilot tests and production bases adhering to international standards. With 13 production lines dedicated to oral solid preparations, oral liquid preparations and API, it is actively expanding its preparation workshops for small-volume injections, soft capsules, eye drops, topical medicines and innovative drug R&D centres.

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Farmhispania

Spain

BioFlorida Conference

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Farmhispania Group, a leading European CDMO in HPAPI Technologies & High Potency Fermentation.

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Spain

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Relugolix

About the Company : Farmhispania Group comprises two companies in Spain: Farmhispania in Barcelona and Rolabo in Zaragoza. Since its inception, the group has consistently invested in advanced equipmen...

Farmhispania Group comprises two companies in Spain: Farmhispania in Barcelona and Rolabo in Zaragoza. Since its inception, the group has consistently invested in advanced equipment, new technologies, and enhanced capabilities. Significant investments include the implementation of hydrogenation technologies in 2007, HPAPI handling capabilities in 2010, highly potent fermentation capabilities in 2014, and the expansion of large-scale preparative chromatography in 2015. Additionally, Farmhispania Group actively collaborates on numerous projects with various universities and research organizations both nationally and internationally.

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Porton Pharma Solutions

China

BioFlorida Conference

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Porton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

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China

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Relugolix

About the Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & operation facilities ar...

Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & operation facilities are located in China, Slovenia, the US, Belgium, Switzerland, Denmark, with more than 6000 employees worldwide. Porton leads the way with its excellent CDMO services, but also supplies APIs & intermediates for the treatment of critical diseases such as HIV/AIDS, diabetes, cancer, & influenza. Our Process Technology Centers & WHO/USFDA/EMA/PDMA/NMPA-inspected Facilities feature state-of-the-art equipment, highly flexible cGMP-compliant production assets.

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API Reference Price

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