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Vidarabine Monohydrate

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Synopsis

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Chemistry

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Also known as: 24356-66-9, Fa2dm6879k, Ci 673, Vidarabine (usan), (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol hydrate, Vidarabine [usan]

Molecular Formula

C₁₀H₁₅N₅O₅

Molecular Weight

285.26 g/mol

InChI Key

ZTHWFVSEMLMLKT-CAMOTBBTSA-N

FDA UNII

FA2DM6879K

A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the VACCINIA VIRUS and varicella zoster virus.

1 2D Structure

Vidarabine Monohydrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;hydrate

2.1.2 InChI

InChI=1S/C10H13N5O4.H2O/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10;/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13);1H2/t4-,6-,7+,10-;/m1./s1

2.1.3 InChI Key

ZTHWFVSEMLMLKT-CAMOTBBTSA-N

2.1.4 Canonical SMILES

C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N.O

2.1.5 Isomeric SMILES

C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N.O

2.2 Other Identifiers

2.2.1 UNII

FA2DM6879K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9 Beta Arabinofuranosyladenine

2. 9 Beta D Arabinofuranosyladenine

3. 9-beta-arabinofuranosyladenine

4. 9-beta-d-arabinofuranosyladenine

5. Adenine Arabinoside

6. Alpha Ara A

7. Alpha D Arabinofuranosyladenine

8. Alpha-ara A

9. Alpha-d-arabinofuranosyladenine

10. Ara A

11. Ara-a

12. Arabinofuranosyladenine

13. Arabinoside, Adenine

14. Arabinosyladenine

15. Beta Ara A

16. Beta-ara A

17. Vidarabine

18. Vira A

19. Vira-a

20. Viraa

2.3.2 Depositor-Supplied Synonyms

1. 24356-66-9

2. Fa2dm6879k

3. Ci 673

4. Vidarabine (usan)

5. (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Hydrate

6. Vidarabine [usan]

7. (2r,3s,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;hydrate

8. Vidarabine [jan]

9. Vidarabine (monohydrate)

10. (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol Hydrate

11. Adenine Arabinofuranoside Hydrate

12. 9-beta-d-arabinofuranosyl-9h-purine-6-amine Monohydrate

13. Drg-0058

14. Unii-fa2dm6879k

15. 9-beta-d-arabinofuranosyladenine Monohydrate

16. Vidarabineh2o

17. Vidarabine H2o

18. Adenine, 9-beta-d-arabinofuranosyl-, Monohydrate

19. Vidarabine [usan:usp:inn:ban:jan]

20. 9h-purin-6-amine, 9-beta-d-arabinofuranosyl-, Monohydrate

21. Vira-a (tn)

22. Vidarabine [vandf]

23. Schembl2929

24. Vidarabine [mart.]

25. Chebi:9978

26. Vidarabine [orange Book]

27. Dtxsid10947210

28. Vidarabine [usp Impurity]

29. 9h-purin-6-amine, 9-.beta.-d-arabinofuranosyl-, Monohydrate

30. Vidarabine Monohydrate [mi]

31. Hy-n6666

32. Mfcd00150980

33. S5297

34. Akos025312428

35. Ccg-267319

36. Nsc 757383

37. Cs-0083211

38. 9-beta-d-arabino Furanosyl Adenine Monohydrate

39. Adenine 9-beta-d-arabinofuranoside Monohydrate

40. C07195

41. D00406

42. T72143

43. Vidarabine (200 Mg)g-2939ug/mg(ai)

44. 9-pentofuranosyl-9h-purin-6-amine--water (1/1)

45. J-015462

46. 9-.beta.-d-arabinofuranosyladenine Monohydrate

47. 9h-purin-6-amine,9-b-d-arabinofuranosyl-,hydrate(1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₅N₅O₅
Molecular Weight	285.26 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Exact Mass	285.10731860 g/mol
Monoisotopic Mass	285.10731860 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	335
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

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.)

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