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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
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 Weight 265.27 g/mol
Molecular Formula C11H15N5O3
XLogP3-2.1
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass265.11748936 g/mol
Monoisotopic Mass265.11748936 g/mol
Topological Polar Surface Area140 Ų
Heavy Atom Count19
Formal Charge0
Complexity334
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


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