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Momelotinib Hydrochloride Hydrate

PubChem CID
102514733
Structure
Momelotinib Hydrochloride Hydrate_small.png
Momelotinib Hydrochloride Hydrate_3D_Structure.png
Molecular Formula
Synonyms
  • Momelotinib dihydrochloride monohydrate
  • LDX8893L5D
  • CYT-387 dihydrochloride monohydrate
  • CYT-11387 dihydrochloride monohydrate
  • UNII-LDX8893L5D
Molecular Weight
505.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2015-12-28
  • Modify:
    2025-01-18
Description
Momelotinib Dihydrochloride Monohydrate is the monohydrate dihydrochloride salt form of momelotinib, an orally bioavailable small molecule inhibitor of wild-type (WT) Janus kinases 1 and 2 (JAK1/2), the JAK2 mutant form JAK2V617F, and activin A receptor type 1 (ACVR1; activin receptor like kinase 2; ALK2), with antineoplastic activity. Upon oral administration, momelotinib competes with JAK1/2 for ATP binding, which results in inhibition of JAK1/2 activation, inhibition of the JAK-STAT signaling pathway, and leads to the induction of apoptosis and a reduction of tumor cell proliferation in JAK1/2-expressing tumor cells. In addition, the inhibition of ALK2 prevents liver hepcidin formation, increases iron availability and increases red blood cell (RBC) production. JAK2 is the most common mutated gene in bcr-abl-negative myeloproliferative disorders; the JAK2V617F gain-of-function mutation involves a valine-to-phenylalanine modification at position 617. The JAK-STAT signaling pathway is a major mediator of cytokine activity and is often dysregulated in a variety of tumor cell types.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Momelotinib Hydrochloride Hydrate.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(cyanomethyl)-4-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]benzamide;hydrate;dihydrochloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C23H22N6O2.2ClH.H2O/c24-10-12-25-22(30)18-3-1-17(2-4-18)21-9-11-26-23(28-21)27-19-5-7-20(8-6-19)29-13-15-31-16-14-29;;;/h1-9,11H,12-16H2,(H,25,30)(H,26,27,28);2*1H;1H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RQKCPSIFARJBOR-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1COCCN1C2=CC=C(C=C2)NC3=NC=CC(=N3)C4=CC=C(C=C4)C(=O)NCC#N.O.Cl.Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C23H26Cl2N6O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1841094-17-4

2.3.2 European Community (EC) Number

991-915-2

2.3.3 UNII

2.3.4 KEGG ID

2.3.5 NCI Thesaurus Code

2.3.6 RXCUI

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
505.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
504.1443441 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
504.1443441 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
104 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
34
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
615
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
0
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
4
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors; Janus Kinase Inhibitors; JAK Inhibitors
Human drug -> Prescription

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors; Janus Kinase Inhibitors; JAK Inhibitors

6.2 FDA National Drug Code Directory

6.3 Drug Labels

Active ingredient and drug

6.4 Cancer Drugs

Drug Name
Brand Name(s)
Ojjaara
FDA Approved
Yes
Drug Use

Momelotinib dihydrochloride monohydrate is approved to treat:

• Myelofibrosis (a bone marrow disease) that is intermediate risk or high risk in adults with anemia, including the following types:

• Primary myelofibrosis.

• Post-polycythemia vera myelofibrosis.

• Post-essential thrombocythemia myelofibrosis.

Momelotinib dihydrochloride monohydrate is also being studied in the treatment of other types of cancer.

6.5 Clinical Trials

6.5.1 EU Clinical Trials Register

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

Pictogram(s)
Irritant
Health Hazard
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Precautionary Statement Codes

P260, P264, P270, P301+P317, P319, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

7.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

STOT RE 2 (100%)

8 Toxicity

8.1 Toxicological Information

8.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the clinical use of momelotinib during breastfeeding. Because momelotinib is 91% bound to plasma proteins, the amount in milk is likely to be low. The manufacturer recommends that breastfeeding be discontinued during momelotinib therapy and for at least 1 week after the last dose.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

9 Patents

9.1 Depositor-Supplied Patent Identifiers

10 Classification

10.1 NCI Thesaurus Tree

10.2 KEGG: Drug

10.3 KEGG: USP

10.4 KEGG: ATC

10.5 KEGG: Target-based Classification of Drugs

10.6 KEGG: Drug Groups

10.7 KEGG: Drug Classes

10.8 ChemIDplus

10.9 UN GHS Classification

11 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    N-(cyanomethyl)-4-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]benzamide;hydrate;dihydrochloride
    https://echa.europa.eu
    N-(cyanomethyl)-4-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]benzamide;hydrate;dihydrochloride (EC: 991-915-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/379479
  3. 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
  4. DailyMed
  5. Drugs and Lactation Database (LactMed)
  6. Drugs@FDA
    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
  7. EU Clinical Trials Register
  8. 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
    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    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
  9. National Drug Code (NDC) Directory
    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
  10. NCI Cancer Drugs
  11. 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
  12. 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
    momelotinib dihydrochloride monohydrate
    https://rxnav.nlm.nih.gov/id/rxnorm/2665205
  13. PubChem
  14. GHS Classification (UNECE)
CONTENTS