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Chemistry

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Also known as: 5536-17-4, Adenine arabinoside, Ara-a, Vira-a, Arabinosyladenine, Spongoadenosine
Molecular Formula
C10H13N5O4
Molecular Weight
267.24  g/mol
InChI Key
OIRDTQYFTABQOQ-UHTZMRCNSA-N
FDA UNII
3XQD2MEW34

Vidarabine
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

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
2.1.2 InChI
InChI=1S/C10H13N5O4/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)/t4-,6-,7+,10-/m1/s1
2.1.3 InChI Key
OIRDTQYFTABQOQ-UHTZMRCNSA-N
2.1.4 Canonical SMILES
C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
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
2.2 Other Identifiers
2.2.1 UNII
3XQD2MEW34
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. Vira A

18. Vira-a

19. Viraa

2.3.2 Depositor-Supplied Synonyms

1. 5536-17-4

2. Adenine Arabinoside

3. Ara-a

4. Vira-a

5. Arabinosyladenine

6. Spongoadenosine

7. Araadenosine

8. Arasena-a

9. 9-beta-d-arabinofuranosyladenine

10. Vidarabine Anhydrous

11. Arabinosyl Adenine

12. Arabinoside Adenine

13. Vidarabin

14. (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

15. Vidarabine [inn]

16. 9-beta-d-arabinofuranosyl-9h-purin-6-amine

17. 9beta-d-arabinofuranosyladenine

18. Nsc-404241

19. Araa

20. 9-beta-d-arabinofuranosyl-adenine

21. Adenine 9-beta-d-arabinofuranoside

22. Vira Atm

23. 6-amino-9-b-d-arabinofuranosylpurine

24. Vidarabine, Anhydrous

25. Vidarabine (vira-a)

26. Adenine 9-beta;-d-arabinofuranoside

27. Vidarabine (jan)

28. Ci-673

29. 2-(6-amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

30. 3xqd2mew34

31. Chembl1090

32. Adenine-beta-d-arabinofuranoside

33. Chebi:45327

34. 9-(beta-d-arabinofuranosyl)adenine

35. 9h-purin-6-amine, 9-.beta.-d-arabinofuranosyl-

36. (2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

37. Nsc-247519

38. Nsc-757383

39. Vidarabina [dcit]

40. Vidarabinum

41. Vidarabina

42. Ci 673

43. Rab

44. 9-beta-arabinoadenosine

45. Beta-d-arabinosyladenine

46. Vidarabinum [inn-latin]

47. Vira A

48. Smr000471872

49. Beta-d-arabinofuranosyladenine

50. Ccris 3383

51. Armes (tn)

52. Adenine Beta-d-arabinofuranoside

53. Hsdb 6514

54. Adenine-9-beta-d-arabinofuranoside

55. Adenine, 9beta-d-arabinofuranosyl-

56. Einecs 226-893-9

57. 9h-purin-6-amine, 9-beta-d-arabinofuranosyl-

58. Adenine, 9-beta-d-arabinofuranosyl-

59. Unii-3xqd2mew34

60. Nsc 247519

61. Brn 0624881

62. 6-amino-9-beta-d-arabinofuranosylpurine

63. Ai3-52821

64. 9h-purin-6-amine, 9beta-d-arabinofuranosyl-

65. 9-.beta.-d-arabinofuranosyl-9h-purin-6-amine

66. Spectrum_001894

67. Vidarabine [mi]

68. Spectrum2_001336

69. Spectrum3_000580

70. Spectrum4_000782

71. Spectrum5_001429

72. Vidarabine [hsdb]

73. (2r,3s,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

74. Vidarabine [who-dd]

75. 9-b-d-arabinofuranosyladenine

76. Bspbio_002000

77. Kbiogr_001224

78. Kbioss_002424

79. Mls001066352

80. Mls001333133

81. Mls001333134

82. Divk1c_000191

83. Schembl110914

84. Spectrum1500609

85. Spbio_001491

86. 9-ss-d-arabinofuranosyladenine

87. Gtpl4806

88. 9-ss -d-arabinofuranosyladenine

89. Hms500j13

90. Kbio1_000191

91. Kbio2_002418

92. Kbio2_004986

93. Kbio2_007554

94. Kbio3_001500

95. Dtxsid80873976

96. 9-beta-d-arabinofuranosyl Adenine

97. Ninds_000191

98. Adenine 9-ss -d-arabinofuranoside

99. Hms1921k05

100. Hms2090f06

101. Hms2092c16

102. Hms2230n24

103. Hms3259i08

104. Hms3714i18

105. Pharmakon1600-01500609

106. Zinc970363

107. Bcp27778

108. Hy-b0277

109. Bdbm50144936

110. Ccg-39634

111. Hg1001

112. Mfcd00065471

113. Nsc757383

114. Pdsp1_001036

115. Pdsp2_001020

116. S1784

117. Akos015919711

118. Db00194

119. Ds-1755

120. Nc00547

121. Idi1_000191

122. Smp1_000312

123. 9-(beta-d-arabinofuranosyl)-9h-adenine

124. 9--d-arabinofuranosyl-9h-purin-6-amine

125. 9h-adenin-9-yl Beta-d-arabinofuranoside

126. Ncgc00023673-08

127. Ncgc00178869-01

128. 6-amino-9-(beta-d-arabinofuranosyl)purine

129. Sbi-0051555.p002

130. Adenine 9-beta-d-arabinofuranoside, >=99%

131. Sw199234-2

132. V0098

133. V0175

134. D06298

135. 9-.beta.-d-arabinofuranosyl-9h-purine-6-amine

136. Ab00430250-08

137. Ab00430250-09

138. Ab00430250_11

139. Ab00430250_12

140. 536v174

141. Q415107

142. Sr-01000765435

143. Sr-05000001737

144. Sr-01000765435-2

145. Sr-05000001737-1

146. Vidarabine, United States Pharmacopeia (usp) Reference Standard

147. (2r,3s,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 267.24 g/mol
Molecular Formula C10H13N5O4
XLogP3-1.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass267.09675391 g/mol
Monoisotopic Mass267.09675391 g/mol
Topological Polar Surface Area140 Ų
Heavy Atom Count19
Formal Charge0
Complexity335
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

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

National Library of Medicine - Medical Subject Headings (2007)


Vidarabine has been shown to possess antiviral activity against the following viruses in vitro: Herpes simplex types 1 and 2; vaccinia, varicella-zoster. Except for rhabdovirus and oncornavirus, vidarabine does not display in vitro antiviral activity against other RNA or DNA viruses, including adenovirus.

FDA; Medwatch. Summary of Safety-Related Drug Labeling Changes Approved by FDA. Vira0A added 10/10/97. Available at www.fda.gov/medwatch/safety/1997/aug97.htm as of March 16, 2007


/EXPTL THER/ When adenovirus causes hemorrhagic cystitis in immunocompromised patients, vidarabine is used for its treatment because therapeutic choice is limited. Although vidarabine has been reported to be effective for these patients, its therapeutic basis has not yet been established. Vidarabine dose-dependently inhibited viral replication as assessed by a yield reduction assay. Viral protein synthesis was dose-dependently inhibited by vidarabine but not at all by acyclovir, and the degree of inhibition by vidarabine was different for each of the viral proteins, ranging from 0-40% of the untreated control. These results indicated the specificity and mechanism of action of vidarabine against adenovirus. The concentration of vidarabine and its metabolite in the bladder is suggested to exhibit effective anti-adenoviral activity in suppressing the replication of adenovirus. Thus, /the authors conclude that their/ results support vidarabine therapy as a possible candidate for adenovirus-induced hemorrhagic cystitis in immunocompromised patients.

PMID:15535050 Kurosaki K et al; Antivir Chem Chemother 15 (5): 281-5 (2004) .


/EXPTL THER/ In the present study, effectiveness of topical vidarabine or subsequent 5-fluorouracil (5-FU) administration was examined against persistent genital human papillomavirus (HPV) infection after local surgery. Thirty patients underwent local eradication treatment of uterine cervical intra-epithelial neoplasia (CIN) and stage Ia1 uterine cervical cancers. HPV typing was performed by PCR-RFLP analysis. HPV infection was detected pre-operatively in 29 of 30 patients. Of these, HPV was still present in the 20 patients within two months after the therapy. Topical administration of vidarabine or subsequent 5-FU once a week for four weeks was performed to the post-operative persistent HPV-positive cases. HPV infection was abolished in 1 of 10 (10%) with topical vidarabine, and in 2 of 4 vidarabine-resistant cases (50%) with topical 5-FU. Topical vidarabine or 5-FU treatment is beneficial for HPV-positive cases after local surgical excision.

PMID:12883720 Niwa K et al; Oncol Rep 10 (5): 1437-41 (2003)


For more Therapeutic Uses (Complete) data for VIDARABINE (18 total), please visit the HSDB record page.


4.2 Drug Warning

Vidarabine has been classified as a potential teratogen and should be used with caution during pregnancy (use only for strong clinical indication in absence of suitable alternative).

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 149


Hallucinosis has been reported with excessive (as opposed to therapeutic) doses /of Vidarabine/.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 666


Vidarabine should be used only under the close supervision of an ophthalmologist.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1700


Concurrent topical application of vidarabine and a corticosteroid is contraindicated in superficial herpes simplex keratitis. Although concomitant application of vidarabine and a corticosteroid may be of benefit in severe infections, corticosteroids should be used with caution and the patient must be observed closely because of the risk of accelerating the spread of the infection. If a topical corticosteroid is administered concurrently with vidarabine, the possibility of corticosteroid induced adverse ocular effects, including increased intraocular pressure, glaucoma, and cataract formation, must be considered.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1700


For more Drug Warnings (Complete) data for VIDARABINE (10 total), please visit the HSDB record page.


4.3 Drug Indication

For treatment of chickenpox - varicella, herpes zoster and herpes simplex


5 Pharmacology and Biochemistry
5.1 Pharmacology

Vidarabine is a synthetic purine nucleoside analogue with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts Vidarabine into Vidarabine monophosphate, a nucleotide analogue. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. In vitro, Vidarabine triphosphate stops the DNA replication of herpes virus by being incorporated into the DNA strand and preventing the formation of phosphodiester bridges between bases. This ultimately leads to destabilization of the viral DNA strands.


5.2 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.)


5.3 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors

J05AB03 - Vidarabine


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AD - Antivirals

S01AD06 - Vidarabine


5.4 Absorption, Distribution and Excretion

Absorption

Systemetic absorption of vidarabine should not be expected to occur following ocular administration and swallowing lacrimal secretions.


Vira-A is rapidly deaminated to arabinosylhypoxanthine (Ara-Hx), the principal metabolite. ...Because of the low solubility of Vira-A, trace amounts of both Vira-A and Ara-Hx can be detected in the aqueous humor only if there is an epithelial defect in the cornea. If the cornea is normal, only trace amounts of Ara-Hx can be recovered from the aqueous humor. Systemic absorption of Vira-A should not be expected to occur following ocular administration and swallowing lacrimal secretions.

FDA; Medwatch. Summary of Safety-Related Drug Labeling Changes Approved by FDA. Vira0A added 10/10/97. Available at www.fda.gov/medwatch/safety/1997/aug97.htm as of March 16, 2007


Vidarabine is poorly absorbed following oral, im, or SC administration. Following iv administration of vidarabine, 75-87% of the dose is rapidly deaminated by adenosine deaminase to ara-hypoxanthine. Ara-hypoxanthine also possesses antiviral activity but substantially less than that of vidarabine. Following slow iv administration of vidarabine 10 mg/kg in adults, peak plasma concentrations of the drug range from 0.2-0.4 ug/mL and peak plasma concentrations of ara-hypoxanthine range from 3-6 ug/mL. Plasma concentrations of vidarabine and ara-hypoxanthine are higher and more prolonged in patients with renal impairment.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 404


Vidarabine and ara-hypoxanthine are widely distributed into body tissues and fluids and readily cross the blood-brain barrier. In patients with normal meninges, ara-hypoxanthine concentrations in the CSF are about 33-35% of concurrent plasma concentrations. Vidarabine crosses the placenta in animals. It is not known if vidarabine is distributed into milk. ... Vidarabine is 20-30% bound and ara-hypoxanthine is 0-3% bound to plasma proteins.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 404


Vidarabine and ara-hypoxanthine are excreted mainly by the kidneys. Within 24 hours following iv administration of vidarabine 15 mg/kg in patients with normal renal function, 1-3% of the dose is excreted in urine as vidarabine and 41-53% of the dose is excreted as ara-hypoxanthine. There is no evidence of fecal excretion of the drug or metabolite.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 404


5.5 Metabolism/Metabolites

In laboratory animals, vidarabine is rapidly deaminated in the gastrointestinal tract to Ara-Hx.


In laboratory animals, Vira-A is rapidly deaminated in the gastrointestinal tract to arabinosylhypoxanthine (Ara-Hx).

FDA; Medwatch. Summary of Safety-Related Drug Labeling Changes Approved by FDA. Vira0A added 10/10/97. Available at www.fda.gov/medwatch/safety/1997/aug97.htm as of March 16, 2007


Vidarabine is rapidly deaminated, possibly within the cornea, by adenosine deaminase to ara-hypoxanthine. Ara-hypoxanthine also possesses antiviral activity but substantially less than that of vidarabine.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1700


5.6 Biological Half-Life

The plasma half-life of vidarabine in adults with normal renal function is 1.5 hr, and the plasma half-life of ara-hypoxanthine is 3.3 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 404


5.7 Mechanism of Action

Vidarabine stops replication of herpes viral DNA in 2 ways: 1) competitive inhibition of viral DNA polymerase, and consequently 2) incorporation into and termination of the growing viral DNA chain. Vidarabine is sequentially phosphorylated by kinases to the triphosphate ara-ATP, which is the active form of vidarabine that acts as both an inhibitor and a substrate of viral DNA polymerase. By acting as a substrate for viral DNA polymerase, ara-ATP competitively inhibits dATP leading to the formation of faulty DNA. Ara-ATP can also be incorporated into the DNA strand to replace many of the adenosine bases, resulting in the disruption of DNA synthesis.


The antiviral mechanism of action has not been established. Vidarabine appears to interfere with the early steps of viral DNA synthesis.

FDA; Medwatch. Summary of Safety-Related Drug Labeling Changes Approved by FDA. Vira-A added 10/10/97. Available at www.fda.gov/medwatch/safety/1997/aug97.htm as of March 16, 2007


The antiviral mechanism of vidarabine is incompletely understood, but vidarabine is an inhibitor of viral DNA synthesis. Cellular enzymes phosphorylate vidarabine to the triphosphate, which inhibits viral DNA polymerase activity in a manner that is competitive with deoxyadenosine triphosphate. Vidarabine triphosphate is incorporated into both cellular and viral DNA, where it may act as a chain terminator. Vidarabine triphosphate also inhibits ribonucleoside reductase, RNA polyadenylation, and S-adenosylhomocysteine hydrolase (SAHH), an enzyme involved in transmethylation reactions.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1328


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