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Opaganib

Granules India Limited has high volume world-class facilities for APIs, PFIs, & FDFs, serving customers in over 80 countries.

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Synopsis

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Chemistry

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Also known as: Abc294640, Opaganib, 915385-81-8, Abc-294640, Abc 294640, Chembl2158685

Molecular Formula

C₂₃H₂₅ClN₂O

Molecular Weight

380.9 g/mol

InChI Key

CAOTVXGYTWCKQE-UHFFFAOYSA-N

FDA UNII

DRG21OQ517

Opaganib is an orally available, aryladamantane compound and selective inhibitor of sphingosine kinase-2 (SK2) with potential antineoplastic activity. Upon administration, opaganib competitively binds to and inhibits SK2, thereby preventing the phosphorylation of the pro-apoptotic amino alcohol sphingosine to sphingosine 1-phosphate (S1P), the lipid mediator that is pro-survival and critical for immunomodulation. This may eventually lead to the induction of apoptosis and may result in an inhibition of cell proliferation in cancer cells overexpressing SK2. SK2 and its isoenzyme SK1 are overexpressed in numerous cancer cell types.

1 2D Structure

Opaganib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)adamantane-1-carboxamide

2.1.2 InChI

InChI=1S/C23H25ClN2O/c24-20-3-1-19(2-4-20)22-10-17-9-18(11-22)13-23(12-17,15-22)21(27)26-14-16-5-7-25-8-6-16/h1-8,17-18H,9-15H2,(H,26,27)

2.1.3 InChI Key

CAOTVXGYTWCKQE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C2CC3(CC1CC(C2)(C3)C(=O)NCC4=CC=NC=C4)C5=CC=C(C=C5)Cl

2.2 Other Identifiers

2.2.1 UNII

DRG21OQ517

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(4-chlorophenyl)-adamantane-1-carboxylic Acid (pyridin-4-ylmethyl)amide

2. 4-pyridinylmethyl-3-(4-chlorophenyl) Adamantane Carboxamide

3. Abc 294640

4. Abc-294640

5. Abc294640

2.3.2 Depositor-Supplied Synonyms

1. Abc294640

2. Opaganib

3. 915385-81-8

4. Abc-294640

5. Abc 294640

6. Chembl2158685

7. 4-pyridinylmethyl-3-(4-chlorophenyl) Adamantane Carboxamide

8. Drg21oq517

9. Yeliva

10. Tricyclo(3.3.1.13,7)decane-1-carboxamide, 3-(4-chlorophenyl)-n-(4-pyridinylmethyl)-

11. Abc294640opaganib

12. Opaganib [inn]

13. Opaganib [who-dd]

14. Opaganib (abc294640)

15. Gtpl6624

16. Schembl1548333

17. Chebi:124965

18. Dtxsid801318727

19. Hms3402p05

20. Amy42174

21. Bcp08959

22. Ex-a1962

23. Bdbm50393642

24. Nsc796101

25. Akos027327311

26. Ccg-268417

27. Cs-0877

28. Db12764

29. Nsc-796101

30. Sb17167

31. Ac-33116

32. As-56117

33. Ba162479

34. Hy-16015

35. S7174

36. Brd-a70814879-003-01-8

37. Q27074100

38. Abc294640

39. 915385-81-8

40. Abc-294640

41. 4-pyridinylmethyl 3(4-chlorophenyl)adamantine Carboxamide

42. (1s,3r,5r,7s)-3-(4-chlorophenyl)-n-(pyridin-4-ylmethyl)adamantane-1-carboxamide

2.4 Create Date

2007-02-12

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₅ClN₂O
Molecular Weight	380.9 g/mol
XLogP3	4.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	380.1655411 g/mol
Monoisotopic Mass	380.1655411 g/mol
Topological Polar Surface Area	42 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	551
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Mechanism of Action

Opaganib selectively inhibits [sphingosine kinase-2 (SK2)](https://go.drugbank.com/polypeptides/Q9NRA0). This inhibition blocks the synthesis of sphingosine 1-phosphate (S1P) and its activities (which includes regulation of fundamental biological processes such as cell proliferation, migration, immune cell trafficking, angiogenesis, immune-modulation, and suppression of innate immune responses from T-cells). This drug has dual anti-inflammatory and antiviral activity targeting a host cell component and is unaffected by viral mutation, contributing to minimization of the likelihood of resistance. It is currently being investigated against COVID-19 as it has demonstrated anti-SARS-CoV-2 activity in studies.

Drugs in Development