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Galidesivir

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Synopsis

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Chemistry

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Also known as: 249503-25-1, Immucillin a, Immucillin-a, Bcx4430, Bcx-4430, Bcx 4430 free base

Molecular Formula

C₁₁H₁₅N₅O₃

Molecular Weight

265.27 g/mol

InChI Key

AMFDITJFBUXZQN-KUBHLMPHSA-N

FDA UNII

OLF97F86A7

Galidesivir is an adenosine analog and RNA polymerase inhibitor, with potential broad-spectrum antiviral activity. Upon administration, galidesivir is metabolized to its monophosphate form, which is then converted into the active triphosphate nucleotide. Galidesivir triphosphate binds to viral RNA-dependent RNA polymerase (RdRp) and gets incorporated into the growing viral RNA strand, which leads to premature chain termination. This prevents viral transcription and replication.

1 2D Structure

Galidesivir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4R,5R)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

2.1.2 InChI

InChI=1S/C11H15N5O3/c12-11-8-6(14-3-15-11)4(1-13-8)7-10(19)9(18)5(2-17)16-7/h1,3,5,7,9-10,13,16-19H,2H2,(H2,12,14,15)/t5-,7+,9-,10+/m1/s1

2.1.3 InChI Key

AMFDITJFBUXZQN-KUBHLMPHSA-N

2.1.4 Canonical SMILES

C1=C(C2=C(N1)C(=NC=N2)N)C3C(C(C(N3)CO)O)O

2.1.5 Isomeric SMILES

C1=C(C2=C(N1)C(=NC=N2)N)[C@H]3[C@@H]([C@@H]([C@H](N3)CO)O)O

2.2 Other Identifiers

2.2.1 UNII

OLF97F86A7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(4-amino-5h-pyrrolo(3,2-d)pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

2. Bcx-4430

3. Bcx4430

4. Imma Cpd

5. Immucillin A

6. Immucillin-a

2.3.2 Depositor-Supplied Synonyms

1. 249503-25-1

2. Immucillin A

3. Immucillin-a

4. Bcx4430

5. Bcx-4430

6. Bcx 4430 Free Base

7. (2s,3s,4r,5r)-2-(4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

8. Olf97f86a7

9. Bcx4430 Freebase

10. Imma Cpd

11. 3,4-pyrrolidinediol,2-(4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)-2s,3s,4r,5r

12. Bcx4430 (freebase)

13. Unii-olf97f86a7

14. (2s,3s,4r,5r)-2-{4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl}-5-(hydroxymethyl)pyrrolidine-3,4-diol

15. Ua2

16. Bcx4430freebase

17. Galidesivir [inn]

18. Galidesivir [who-dd]

19. Chembl1236524

20. Schembl12468816

21. Gtpl11920

22. Ex-a6295

23. Bdbm50513995

24. Hy-18649a

25. Zinc13492903

26. Cs-3779

27. Db11676

28. Ncgc00485882-01

29. Bcx-4430 Freebase;immucillin-a;galidesivir

30. P14655

31. A900809

32. (1s)-1-(9-carbaadenine-9-yl)-1,4-dideoxy-1,4-imino-d-ribitol

33. 3,4-pyrrolidinediol, 2-(4-amino-5h-pyrrolo(3,2-d)pyrimidin-7-yl)-5-(hydroxymethyl)-, (2s,3s,4r,5r)-

34. Galidesivir; Bcx4430; Bcx 4430; Bcx-4430;(2s,3s,4r,5r)-2-(4-amino-5h-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₅N₅O₃
Molecular Weight	265.27 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	265.11748936 g/mol
Monoisotopic Mass	265.11748936 g/mol
Topological Polar Surface Area	140 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	334
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Pharmacology

Galidesivir is an adenosine analogue with a broad-spectrum antiviral activity against RNA viruses, including flaviviruses, togaviruses, bunyaviruses, arenaviruses, paramyxoviruses, coronaviruses, filoviruses, orthomyxoviruses, and picornaviruses.

4.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

4.3 Mechanism of Action

Galidesivir works by binding to viral RNA polymerase where the natural nucleotide would bind, leading to the structural change in the viral enzyme due to altered electrostatic interactions. Disruption of viral RNA polymerase activity results in premature termination of the elongating RNA strand.

Drugs in Development