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Telotristat

PubChem CID
25025298
Structure
Telotristat_small.png
Telotristat_3D_Structure.png
Molecular Formula
Synonyms
  • Telotristat
  • 1033805-28-5
  • LP-778902
  • UNII-381V4FCV2Z
  • 381V4FCV2Z
Molecular Weight
546.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2008-11-17
  • Modify:
    2025-01-18
Description
Telotristat is a phenylalanine derivative.
A tryptophan hydroxylase inhibitor. [Telotristat ethyl] (brand name Xermelo) is a prodrug of telotristat.
Telotristat is a Tryptophan Hydroxylase Inhibitor. The mechanism of action of telotristat is as a Tryptophan Hydroxylase Inhibitor.
See also: Telotristat Ethyl (active moiety of); Telotristat Etiprate (is active moiety of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Telotristat.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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]propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

NCLGDOBQAWBXRA-PGRDOPGGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=NN(C=C1)C2=C(C=CC(=C2)Cl)[C@H](C(F)(F)F)OC3=NC(=NC(=C3)C4=CC=C(C=C4)C[C@@H](C(=O)O)N)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C25H22ClF3N6O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1033805-28-5

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 NCI Thesaurus Code

2.3.10 Pharos Ligand ID

2.3.11 RXCUI

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • LX1606
  • telotristat
  • telotristat etiprate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
546.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
546.1394008 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
546.1394008 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
142 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
38
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
790
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

6.2 LiverTox Summary

Telotristat is an oral, small molecule inhibitor of tryptophan hydroxylase that is used in the treatment of symptoms of carcinoid syndrome. Telotristat is associated with modest rate of minor serum enzyme elevations during therapy but has not been linked to cases of clinically apparent liver injury.

6.3 Drug Classes

Antineoplastic Agents

6.4 Clinical Trials

6.4.1 ClinicalTrials.gov

7 Pharmacology and Biochemistry

7.1 FDA Pharmacological Classification

FDA UNII
381V4FCV2Z
Active Moiety
TELOTRISTAT
Pharmacological Classes
Established Pharmacologic Class [EPC] - Tryptophan Hydroxylase Inhibitor
Pharmacological Classes
Mechanisms of Action [MoA] - Tryptophan Hydroxylase Inhibitors
FDA Pharmacology Summary
Telotristat is a Tryptophan Hydroxylase Inhibitor. The mechanism of action of telotristat is as a Tryptophan Hydroxylase Inhibitor.

7.2 ATC Code

A - Alimentary tract and metabolism

A16 - Other alimentary tract and metabolism products

A16A - Other alimentary tract and metabolism products

A16AX - Various alimentary tract and metabolism products

A16AX15 - Telotristat

8 Toxicity

8.1 Toxicological Information

8.1.1 Hepatotoxicity

In small clinical trials of telotristat in patients with neuroendocrine tumors and symptomatic diarrhea despite stable doses of somatostatin analogues, transient, asymptomatic and mild serum elevations of ALT occurred in 4% to 5% and of GGT in 6% to 9% of treated subjects. Apparent liver injury with jaundice was not observed in the several prelicensure clinical trials and has not been reported in the limited clinical experience with this agent since its approval.

Likelihood score: E (unlikely cause of clinically apparent liver injury).

9 Associated Disorders and Diseases

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

12.2 Drug-Drug Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 NCI Thesaurus Tree

14.3 ChEBI Ontology

14.4 KEGG: ATC

14.5 KEGG: Target-based Classification of Drugs

14.6 WHO ATC Classification System

14.7 FDA Pharm Classes

14.8 ChemIDplus

14.9 ChEMBL Target Tree

14.10 EPA DSSTox Classification

14.11 PFAS and Fluorinated Organic Compounds in PubChem

14.12 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. ChEBI
  2. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  3. FDA Pharm Classes
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. LiverTox
  5. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  6. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  12. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  13. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  14. Metabolomics Workbench
  15. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  16. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  17. Springer Nature
  18. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  19. Wikidata
  20. PubChem
  21. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
  24. NCBI
CONTENTS