vidarabine

Trade name: vira-a

Small moleculeapproved

Approved

Nov 26, 1976

Vidarabine or 9-β-D-arabinofuranosyladenine (ara-A, trade name Vira-A) is a synthetic purine nucleoside analog 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 analog. 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 replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, Vidarabine triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where Vidarabine triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand. — NCATS

Clinical trial activity

1 trials · 1 clinical orgs · 2 marketing orgs

Phase 1
0
Phase 2
1
Phase 3
1
Phase 4
0

Earliest trial started Nov 2, 1999 (NCT00000985)

Timeline

1970s

  1. Nov 26, 1976

    Parke-Davis — Earliest FDA Approval

  2. Nov 26, 1976

    Parke-Davis — NDA Organization

  3. Nov 26, 1976

    Parke-Davis — NDA Secondary Org

  4. Nov 26, 1976

    Warner Lambert — NDA Secondary Org

1990s

  1. Jan 1, 1999

    Earliest Phase 3 Sponsor(trial)

Indications

Mechanism of action

Approval history

  • approvedPriority reviewNov 26, 1976

Chemistry & pharmacology

Loading structure…

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
Mol. weight
267.2413 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral, Topical
Availability
Discontinued

Oral

No

Parenteral

Yes

Topical

Yes

Sources

Also known as

  • 2-(6-amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  • 2-(6-amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  • 9-beta-d-arabinofuranosyl-9h-purin-6-amine
  • 9-beta-d-arabinofuranosyl-9h-purin-6-amine
  • 9-beta-d-arabinofuranosyladenine
  • 9-beta-d-arabinofuranosyladenine
  • 9-beta-d-arabinofuranosyl-adenine
  • 9-beta-d-arabinofuranosyl-adenine
  • 9-β-d-arabinofuranosyl-9h-purin-6-amine
  • 9-β-d-arabinofuranosyl-9h-purin-6-amine
  • 9-β-d-arabinofuranosyladenine
  • 9-β-d-arabinofuranosyladenine
  • adenine arabinoside
  • ara-a
  • ara-a
  • araadenosine
  • arabinosyladenine
  • arabinosyladenine
  • arabinosyladenine
  • ci-673
  • ci-673
  • spongoadenosine
  • spongoadenosine
  • vidarabin
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vidarabine
  • vira-a
  • vira-a
  • vira-a

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT00000985Phase 3Nov 2, 1999National Institute of Allergy and Infectious Diseases (NIAID)
Showing 1 of 1 trials
Page 1 / 1

Organizations

Research & Development (1)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Institute of Allergy and Infectious Diseases (NIAID)Government1111999
1 organizations
Page 1 / 1

Marketing (3)

OrganizationOrg typeRelationshipDate
Parke-DavisFor profitNDANov 26, 1976
Parke-DavisFor profitNDA2Nov 26, 1976
Warner LambertFor profitNDA2Nov 26, 1976