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Also known as: 1137608-69-5, Lx1606 hippurate, Telotristat ethyl hippurate, Lx1032 hippurate, Telotristat etiprate [usan], Lx 1606 hippurate

Molecular Formula

C₃₆H₃₅ClF₃N₇O₆

Molecular Weight

754.2 g/mol

InChI Key

XSFPZBUIBYMVEA-CELUQASASA-N

FDA UNII

3T25U84H4U

Telotristat Etiprate is an orally bioavailable, small-molecule, tryptophan hydroxylase (TPH) inhibitor prodrug, with potential antiserotonergic activity. Upon administration, telotristat etiprate is converted to its active moiety, telotristat (LP-778902), which binds to and blocks 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 Etiprate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-benzamidoacetic acid;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.C9H9NO3/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;11-8(12)6-10-9(13)7-4-2-1-3-5-7/h4-11,13-14,20,24H,3,12,32H2,1-2H3,(H2,33,34,35);1-5H,6H2,(H,10,13)(H,11,12)/t20-,24+;/m0./s1

2.1.3 InChI Key

XSFPZBUIBYMVEA-CELUQASASA-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.C1=CC=C(C=C1)C(=O)NCC(=O)O

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.C1=CC=C(C=C1)C(=O)NCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

3T25U84H4U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lx1606

2. Telotristat

2.3.2 Depositor-Supplied Synonyms

1. 1137608-69-5

2. Lx1606 Hippurate

3. Telotristat Ethyl Hippurate

4. Lx1032 Hippurate

5. Telotristat Etiprate [usan]

6. Lx 1606 Hippurate

7. Lx1606 (hippurate)

8. 1137608-69-5 (etiprate)

9. Lx-1606 Hippurate

10. 3t25u84h4u

11. Telotristat Etiprate (usan)

12. 2-benzamidoacetic Acid, ((s)-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)-1-ethoxy-1-oxopr

13. (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 2-benzamidoacetate .

14. 4-[2-amino-6-[(1r)-1-[4-chloro-2-(3-methyl-1h-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-4-pyrimidinyl]-l-phenylalanine Ethyl Ester N-benzoylglycine Salt

15. Telotristat Etiprate (lx 1606 Hippurate)

16. Unii-3t25u84h4u

17. Lx 1032 Hippurate

18. Lx-1032 Hippurate

19. Chembl3348963

20. Telotristat Etiprate [mi]

21. Amy38702

22. Ex-a1619

23. S2173

24. Telotristat Etiprate [who-dd]

25. Akos027250730

26. Ccg-270440

27. Cs-0429

28. Ncgc00346476-01

29. (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 Hippurate

30. 4-[2-amino-6-[(1r)-1-[4-chloro-2-(3-methyl-1h-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-4-pyrimidi

31. Ac-30898

32. Hy-13055

33. Telotristat Etiprate [orange Book]

34. Sw219281-1

35. D09975

36. Q27257995

37. 2-benzamidoacetic Acid, ((s)-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)-1-ethoxy-1-oxopropan-2-yl)amide Salt

38. 2-benzamidoacetic Acid;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

39. 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 N-benzoylglycinate (1:1)

40. 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, Compd. With N-benzoylglycine (1:1)

2.4 Create Date

2009-05-18

3 Chemical and Physical Properties

Molecular Formula	C₃₆H₃₅ClF₃N₇O₆
Molecular Weight	754.2 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	13
Exact Mass	753.2289440 g/mol
Monoisotopic Mass	753.2289440 g/mol
Topological Polar Surface Area	198 Å²
Heavy Atom Count	53
Formal Charge	0
Complexity	1020
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	2

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

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

Treatment of carcinoid syndrome

5 Pharmacology and Biochemistry

5.1 ATC Code

A16A