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Polfa Tarchomin is a leading Polish pharmaceutical company with 200 year tradition in manufacture and sale of pharmaceutical products.

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Also known as: 1033805-22-9, Lx1606, Lx 1606, Xermelo, (s)-ethyl 2-amino-3-(4-(2-amino-6-((r)-1-(4-chloro-2-(3-methyl-1h-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoate, Lx-1606

Molecular Formula

C₂₇H₂₆ClF₃N₆O₃

Molecular Weight

575.0 g/mol

InChI Key

MDSQOJYHHZBZKA-GBXCKJPGSA-N

FDA UNII

8G388563M7

Telotristat Ethyl is the ethyl ester form of telotristat, a tryptophan hydroxylase (TPH) inhibitor, with potential anti-serotonergic activity. Upon administration, telotristat binds to and inhibits the activity of TPH. This may result in a reduction in peripheral serotonin (5-HT) production and improvement of serotonin-mediated gastrointestinal effects such as severe diarrhea. TPH, the rate-limiting enzyme in serotonin biosynthesis, is overexpressed in carcinoid tumor cells.

1 2D Structure

Telotristat Ethyl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl (2S)-2-amino-3-[4-[2-amino-6-[(1R)-1-[4-chloro-2-(3-methylpyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]phenyl]propanoate

2.1.2 InChI

InChI=1S/C27H26ClF3N6O3/c1-3-39-25(38)20(32)12-16-4-6-17(7-5-16)21-14-23(35-26(33)34-21)40-24(27(29,30)31)19-9-8-18(28)13-22(19)37-11-10-15(2)36-37/h4-11,13-14,20,24H,3,12,32H2,1-2H3,(H2,33,34,35)/t20-,24+/m0/s1

2.1.3 InChI Key

MDSQOJYHHZBZKA-GBXCKJPGSA-N

2.1.4 Canonical SMILES

CCOC(=O)C(CC1=CC=C(C=C1)C2=CC(=NC(=N2)N)OC(C3=C(C=C(C=C3)Cl)N4C=CC(=N4)C)C(F)(F)F)N

2.1.5 Isomeric SMILES

CCOC(=O)[C@H](CC1=CC=C(C=C1)C2=CC(=NC(=N2)N)O[C@H](C3=C(C=C(C=C3)Cl)N4C=CC(=N4)C)C(F)(F)F)N

2.2 Other Identifiers

2.2.1 UNII

8G388563M7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lx1032

2. Xermelo

2.3.2 Depositor-Supplied Synonyms

1. 1033805-22-9

2. Lx1606

3. Lx 1606

4. Xermelo

5. (s)-ethyl 2-amino-3-(4-(2-amino-6-((r)-1-(4-chloro-2-(3-methyl-1h-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoate

6. Lx-1606

7. Telotristat Ethyl [usan]

8. Lx 1032

9. Lx1032

10. Lx-1032

11. Ethyl (2s)-2-amino-3-[4-[2-amino-6-[(1r)-1-[4-chloro-2-(3-methylpyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]phenyl]propanoate

12. 8g388563m7

13. Telotristat Ethyl (usan)

14. Lx-1606 Hippurate

15. Telotristat Etiprate (lx 1606 Hippurate)

16. Telotristat-ethyl

17. Unii-8g388563m7

18. Xermelo (tn)

19. Schembl610588

20. Telotristat Ethyl [mi]

21. Gtpl9490

22. Chembl2105695

23. Ex-a322

24. Bdbm445704

25. Dtxsid001102271

26. Telotristat Ethyl [who-dd]

27. Amy38688

28. Hy-13055a

29. Lx1606lx1606

30. Mfcd18251583

31. Zinc43205655

32. Bcp9000866

33. Db12095

34. Us10683309, Example Lx1606

35. Ncgc00390241-01

36. Ncgc00390241-07

37. As-35061

38. D09974

39. J-524318

40. Q27270371

41. Ethyl 4-(2-amino-6-((1r)-1-(4-chloro-2-(3-methyl-1h-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pryrimidin-4-yl)-l-phenylalaninate

42. L-phenylalanine, 4-(2-amino-6-((1r)-1-(4-chloro-2-(3-methyl-1h-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)-4-pryrimidinyl)-, Ethyl Ester

2.4 Create Date

2009-03-16

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₆ClF₃N₆O₃
Molecular Weight	575.0 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	10
Exact Mass	574.1707009 g/mol
Monoisotopic Mass	574.1707009 g/mol
Topological Polar Surface Area	131 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	821
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Information

1 of 1
Drug Name	XERMELO
Active Ingredient	TELOTRISTAT ETIPRATE
Company	LEXICON PHARMS INC (Application Number: N208794. Patents: 7553840, 7709493, 7968559, 8193204, 8653094)

4.2 Drug Indication

As a serotonin synthesis inhibitor, telotristat etiprate, has the potential to reduce serotonin levels and address the key elements of carcinoid syndrome.

Xermelo is indicated for the treatment of carcinoid syndrome diarrhoea in combination with somatostatin analogue (SSA) therapy in adults inadequately controlled by SSA therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Activity is mainly in the gastrointestinal tract, with minimal effects reported on the brain and cardiovascular system, accompanied by an excellent safety profile. In normal mice, telotristat etiprate (administered once daily for 4 days at doses of 15300 mg/kg/day) was found to reduce serotonin levels throughout the gastrointestinal tract. These reductions occurred in a dose dependent fashion with maximal effects observed with doses of telotristat etiprate 150 mg/kg. No significant change in brain serotonin or 5-hydroxyindoleacetic acid (5-HIAA, a serotonin metabolite) was observed. Similar findings were seen in Sprague-Dawley rats. Gastrointestinal motility studies were conducted in rats using the charcoal meal test. There was a significant dose-related delay in both gastrointestinal transit and gastric emptying, associated with a reduction in blood serotonin levels and proximal colon serotonin. A quantitative whole-body autoradiography study was conducted to assess the absorption, distribution and excretion of radioactivity in rats following a single oral dose of telotristat etiprate labeled with carbon 14. Rats were administered either 30 mg/kg or 100 mg/kg of the compound. The distribution of radioactivity was limited to tissues of the hepatic and renal system and the contents of the GI tract. There was no measurable radioactivity in the brain at any dose tested.

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Tryptophan Hydroxylase Inhibitors [MoA]; Tryptophan Hydroxylase Inhibitor [EPC]

5.3 ATC Code

A16A

5.4 Absorption, Distribution and Excretion

Absorption

Low systemic absorption. Tmax of 24 h, supporting the 8-hourly administration

Route of Elimination

Telotristat ethyl is mainly excreted in feces.

Clearance

Not available

5.5 Metabolism/Metabolites

Metabolized by the liver.

5.6 Biological Half-Life

412 h

5.7 Mechanism of Action

Telotristat etiprate is an ethyl ester prodrug which is hydrolyzed to its active moiety LP-778902 both in vivo and in vitro. Systemic exposure of telotristat etiprate is relatively low, as the hydrolysis to the active moiety is rapid. LP-778902 is a potent inhibitor of TPH with an in vivo IC50 of 0.028 M. While existing treatments for carcinoid syndrome work to reduce the release of serotonin outside tumor cells, telotristat etiprate works at the source to reduce serotonin production within the tumor cells. By specifically inhibiting serotonin production, telotristat etiprate seeks to control this important driver of carcinoid syndrome and, in turn, provide patients with more control over their disease.

Drugs in Development

01 TerSera Therapeutics

U.S.A

PharmaVenue

Not Confirmed

02 Lexicon pharmaceuticals

U.S.A

PharmaVenue

Not Confirmed

03 Lexicon pharmaceuticals

U.S.A

PharmaVenue

Not Confirmed

04 Lexicon pharmaceuticals

U.S.A

PharmaVenue

Not Confirmed

05 Lexicon pharmaceuticals

U.S.A

PharmaVenue

Not Confirmed

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ABOUT THIS PAGE

Telotristat Ethyl Manufacturers

A Telotristat Ethyl manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Telotristat Ethyl, including repackagers and relabelers. The FDA regulates Telotristat Ethyl manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Telotristat Ethyl API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Telotristat Ethyl Suppliers

A Telotristat Ethyl supplier is an individual or a company that provides Telotristat Ethyl active pharmaceutical ingredient (API) or Telotristat Ethyl finished formulations upon request. The Telotristat Ethyl suppliers may include Telotristat Ethyl API manufacturers, exporters, distributors and traders.

Telotristat Ethyl GMP

Telotristat Ethyl Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Telotristat Ethyl GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Telotristat Ethyl GMP manufacturer or Telotristat Ethyl GMP API supplier for your needs.

Telotristat Ethyl CoA

A Telotristat Ethyl CoA (Certificate of Analysis) is a formal document that attests to Telotristat Ethyl's compliance with Telotristat Ethyl specifications and serves as a tool for batch-level quality control.

Telotristat Ethyl CoA mostly includes findings from lab analyses of a specific batch. For each Telotristat Ethyl CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Telotristat Ethyl may be tested according to a variety of international standards, such as European Pharmacopoeia (Telotristat Ethyl EP), Telotristat Ethyl JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Telotristat Ethyl USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.

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4 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

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