vidarabine
Trade name: vira-a
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
Earliest trial started Nov 2, 1999 (NCT00000985)
Timeline
1970s
- Nov 26, 1976
Parke-Davis — Earliest FDA Approval
- Nov 26, 1976
Parke-Davis — NDA Organization
- Nov 26, 1976
Parke-Davis — NDA Secondary Org
- Nov 26, 1976
Warner Lambert — NDA Secondary Org
1990s
- Jan 1, 1999
Earliest Phase 3 Sponsor(trial)
Indications
Approved for
Mechanism of action
- Human herpesvirus 1 DNA polymeraseINHIBITOR
Human herpesvirus 1 DNA polymerase inhibitor
Approval history
- approvedPriority reviewNov 26, 1976
Chemistry & pharmacology
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
- WikipediaVidarabine ↗
- NCATS3XQD2MEW34 ↗
- ChEMBLCHEMBL1090 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT00000985 | Phase 3 | Nov 2, 1999 | National Institute of Allergy and Infectious Diseases (NIAID) |
Organizations
Research & Development (1)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 1 | 1 | 1 | 1999 |
Marketing (3)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Parke-Davis | For profit | NDA | Nov 26, 1976 |
| Parke-Davis | For profit | NDA2 | Nov 26, 1976 |
| Warner Lambert | For profit | NDA2 | Nov 26, 1976 |