Telotristat
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MedKoo CAT#: 319779

CAS#: 1033805-28-5 (acid)

Description: Telotristat, also known as LP-778902, is the acid form of Telotristat ethyl, and the active metabolite of LX1606 (Telotristat etiprate), which is an orally bioavailable, small-molecule, tryptophan hydroxylase (TPH) inhibitor and serotonin synthesis inhibitor with potential antiserotonergic activity. Blocking peripheral serotonin synthesis by telotristat reduces severity of both chemical- and infection-induced intestinal inflammation.


Price and Availability

Size
Price

1g
USD 3650
Size
Price

2g
USD 5650
Size
Price

5g
USD 8650

Telotristat, purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 2 months after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319779
Name: Telotristat
CAS#: 1033805-28-5 (acid)
Chemical Formula: C25H22ClF3N6O3
Exact Mass: 546.1394
Molecular Weight: 546.9352
Elemental Analysis: C, 54.90; H, 4.05; Cl, 6.48; F, 10.42; N, 15.37; O, 8.78


Related CAS #: 1137608-69-5 (etiprate)   1033805-22-9 (ethyl)   1033805-28-5 (acid)  

Synonym: LP-778902; LP 778902; LP778902; Telotristat

IUPAC/Chemical Name: (S)-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)propanoic acid

InChi Key: NCLGDOBQAWBXRA-PGRDOPGGSA-N

InChi Code: InChI=1S/C25H22ClF3N6O3/c1-13-8-9-35(34-13)20-11-16(26)6-7-17(20)22(25(27,28)29)38-21-12-19(32-24(31)33-21)15-4-2-14(3-5-15)10-18(30)23(36)37/h2-9,11-12,18,22H,10,30H2,1H3,(H,36,37)(H2,31,32,33)/t18-,22+/m0/s1

SMILES Code: O=C(O)[C@@H](N)CC1=CC=C(C2=NC(N)=NC(O[C@H](C3=CC=C(Cl)C=C3N4N=C(C)C=C4)C(F)(F)F)=C2)C=C1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
CAS#1033805-22-9 (Telotristat ethyl)
CAS#1033805-28-5 (Telotristat)
CAS#1137608-69-5 (Telotristat etiprate)


References

1: Welford RW, Vercauteren M, Trébaul A, Cattaneo C, Eckert D, Garzotti M, Sieber P, Segrestaa J, Studer R, Groenen PM, Nayler O. Serotonin biosynthesis as a predictive marker of serotonin pharmacodynamics and disease-induced dysregulation. Sci Rep. 2016 Jul 21;6:30059. doi: 10.1038/srep30059. PubMed PMID: 27444653; PubMed Central PMCID: PMC4956766.

2: Mehrvarz Sarshekeh A, Halperin DM, Dasari A. Update on management of midgut neuroendocrine tumors. Int J Endocr Oncol. 2016 May;3(2):175-189. Epub 2016 Apr 8. PubMed PMID: 27347369; PubMed Central PMCID: PMC4915384.

3: Singh S, Asa SL, Dey C, Kennecke H, Laidley D, Law C, Asmis T, Chan D, Ezzat S, Goodwin R, Mete O, Pasieka J, Rivera J, Wong R, Segelov E, Rayson D. Diagnosis and management of gastrointestinal neuroendocrine tumors: An evidence-based Canadian consensus. Cancer Treat Rev. 2016 Jun;47:32-45. doi: 10.1016/j.ctrv.2016.05.003. Epub 2016 May 17. Review. PubMed PMID: 27236421.

4: Cives M, Soares HP, Strosberg J. Will clinical heterogeneity of neuroendocrine tumors impact their management in the future? Lessons from recent trials. Curr Opin Oncol. 2016 Jul;28(4):359-66. doi: 10.1097/CCO.0000000000000299. PubMed PMID: 27138571.

5: Molina-Cerrillo J, Alonso-Gordoa T, Martínez-Sáez O, Grande E. Inhibition of Peripheral Synthesis of Serotonin as a New Target in Neuroendocrine Tumors. Oncologist. 2016 Jun;21(6):701-7. doi: 10.1634/theoncologist.2015-0455. Epub 2016 Apr 22. Review. PubMed PMID: 27107003; PubMed Central PMCID: PMC4912367.

6: Gelhorn HL, Kulke MH, O'Dorisio T, Yang QM, Jackson J, Jackson S, Boehm KA, Law L, Kostelec J, Auguste P, Lapuerta P. Patient-reported Symptom Experiences in Patients With Carcinoid Syndrome After Participation in a Study of Telotristat Etiprate: A Qualitative Interview Approach. Clin Ther. 2016 Apr;38(4):759-68. doi: 10.1016/j.clinthera.2016.03.002. Epub 2016 Mar 31. PubMed PMID: 27041406.

7: Boutzios G, Kaltsas G. Clinical Syndromes Related to Gastrointestinal Neuroendocrine Neoplasms. Front Horm Res. 2015;44:40-57. doi: 10.1159/000382053. Epub 2015 Aug 14. Review. PubMed PMID: 26303703.

8: Kim JJ, Wang H, Terc JD, Zambrowicz B, Yang QM, Khan WI. Blocking peripheral serotonin synthesis by telotristat etiprate (LX1032/LX1606) reduces severity of both chemical- and infection-induced intestinal inflammation. Am J Physiol Gastrointest Liver Physiol. 2015 Sep 15;309(6):G455-65. doi: 10.1152/ajpgi.00299.2014. Epub 2015 Jul 23. PubMed PMID: 26206858.

9: Pavel M, Hörsch D, Caplin M, Ramage J, Seufferlein T, Valle J, Banks P, Lapuerta P, Sands A, Zambrowicz B, Fleming D, Wiedenmann B. Telotristat etiprate for carcinoid syndrome: a single-arm, multicenter trial. J Clin Endocrinol Metab. 2015 Apr;100(4):1511-9. doi: 10.1210/jc.2014-2247. Epub 2015 Jan 30. PubMed PMID: 25636046.

10: Kulke MH, O'Dorisio T, Phan A, Bergsland E, Law L, Banks P, Freiman J, Frazier K, Jackson J, Yao JC, Kvols L, Lapuerta P, Zambrowicz B, Fleming D, Sands A. Telotristat etiprate, a novel serotonin synthesis inhibitor, in patients with carcinoid syndrome and diarrhea not adequately controlled by octreotide. Endocr Relat Cancer. 2014 Oct;21(5):705-14. doi: 10.1530/ERC-14-0173. Epub 2014 Jul 10. PubMed PMID: 25012985; PubMed Central PMCID: PMC4295770.

11: Margolis KG, Stevanovic K, Li Z, Yang QM, Oravecz T, Zambrowicz B, Jhaver KG, Diacou A, Gershon MD. Pharmacological reduction of mucosal but not neuronal serotonin opposes inflammation in mouse intestine. Gut. 2014 Jun;63(6):928-37. doi: 10.1136/gutjnl-2013-304901. Epub 2013 Jun 7. PubMed PMID: 23749550; PubMed Central PMCID: PMC4034681.