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CAS 1191237-69-0
Also known as: Gs-441524, 1191237-69-0, Gs441524, Gs 441524, Evo984, (2r,3r,4s,5r)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile
Molecular Formula
C12H13N5O4
Molecular Weight
291.26  g/mol
InChI Key
BRDWIEOJOWJCLU-LTGWCKQJSA-N
FDA UNII
1BQK176DT6

GS-441524 is an adenosine nucleotide analog antiviral, similar to [remdesivir]. This molecule was patented in 2009. In vitro studies of GS-441524 have determined it has a higher EC50 than remdesivir against a number of viruses, meaning GS-441524 is less potent. GS-441524 continues to be studied in the treatment of Feline Infectious Peritonitis Virus, a coronavirus that only infects cats.
1 2D Structure

CAS 1191237-69-0

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile
2.1.2 InChI
InChI=1S/C12H13N5O4/c13-4-12(10(20)9(19)7(3-18)21-12)8-2-1-6-11(14)15-5-16-17(6)8/h1-2,5,7,9-10,18-20H,3H2,(H2,14,15,16)/t7-,9-,10-,12+/m1/s1
2.1.3 InChI Key
BRDWIEOJOWJCLU-LTGWCKQJSA-N
2.1.4 Canonical SMILES
C1=C2C(=NC=NN2C(=C1)C3(C(C(C(O3)CO)O)O)C#N)N
2.1.5 Isomeric SMILES
C1=C2C(=NC=NN2C(=C1)[C@]3([C@@H]([C@@H]([C@H](O3)CO)O)O)C#N)N
2.2 Other Identifiers
2.2.1 UNII
1BQK176DT6
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (13c3)-gs-441524

2. (2r,3r,4s,5r)-2-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furancarbonitrile

3. 13c3 Gs-441524

4. 13c3-gs-441524

5. 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-d-altrononitrile

6. Gs 441524

7. Gs-441285

8. Gs-441524

9. Gs-828840

10. Gs441524

2.3.2 Depositor-Supplied Synonyms

1. Gs-441524

2. 1191237-69-0

3. Gs441524

4. Gs 441524

5. Evo984

6. (2r,3r,4s,5r)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile

7. Evo-984

8. 1bqk176dt6

9. Evo 984

10. 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-d-altrononitrile

11. 2-c-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-d-altrononitrile

12. D-altrononitrile, 2-c-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-

13. (2~{r},3~{r},4~{s},5~{r})-2-(4-azanylpyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolane-2-carbonitrile

14. Reacted Form

15. Mfcd32666994

16. (2r,3r,4s,5r)-2-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile

17. U08

18. Unii-1bqk176dt6

19. Chembl2016757

20. Schembl10120689

21. Gtpl11445

22. Chebi:147281

23. Dtxsid201028047

24. Ex-a3056

25. Remdesivir Metabolite(gs-441524)

26. Bdbm50571531

27. S6814

28. Zb1788

29. Gs 441524 [who-dd]

30. Akos037648588

31. Remdesivir Intermediate(gs-441524)

32. Bcp29949-1

33. (2r,3r,4s,5r)-2-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furancarbonitrile

34. Ac-31365

35. Bs-14744

36. Hy-103586

37. Cs-0028160

38. C22275

39. D78523

40. A933921

41. (2r,3r,4s,5r)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

2.4 Create Date
2009-11-30
3 Chemical and Physical Properties
Molecular Weight 291.26 g/mol
Molecular Formula C12H13N5O4
XLogP3-1.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass291.09675391 g/mol
Monoisotopic Mass291.09675391 g/mol
Topological Polar Surface Area150 Ų
Heavy Atom Count21
Formal Charge0
Complexity456
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 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.)


4.2 Absorption, Distribution and Excretion

Absorption

GS-441524 has been found to transport poorly into cells compared to remdesivir.


4.3 Metabolism/Metabolites

GS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate.


4.4 Mechanism of Action

GS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate, which is incorporated into the genome of virions, terminating its replication.


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