WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 318978
CAS#: 5536-17-4
Description: Vidarabine is an antiviral drug which is active against herpes simplex and varicella zoster viruses. The drug was originally intended as an anti-cancer drug. The anti-viral activity of vidarabine was first described by M. Privat de Garilhe and J. De Rudder in 1964. It was the first nucleoside analog antiviral to be given systemically and was the first agent to be licensed for the treatment of systematic herpes virus infection in humans. It was University of Alabama at Birmingham researcher and physician Dr. Richard Whitley in 1976 where the clinical effectiveness of vidarabine was first realized, and vidarabine was used in the treatment of many viral diseases.
MedKoo Cat#: 318978
Name: Vidarabine
CAS#: 5536-17-4
Chemical Formula: C10H13N5O4
Exact Mass: 267.09675
Molecular Weight: 267.245
Elemental Analysis: C, 44.94; H, 4.90; N, 26.21; O, 23.95
Related CAS #: 5536-17-4 (free) 24356-66-9 (hydrate)
Synonym: Vira A; Vira-A; ViraA; Ara-A; Ara A; Arabinofuranosyladenine; 9-beta-Arabinofuranosyladenine; Vidarabine.
IUPAC/Chemical Name: (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChi Key: OIRDTQYFTABQOQ-UHTZMRCNSA-N
InChi Code: 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
SMILES Code: O[C@@H]1[C@H](N2C=NC3=C(N)N=CN=C23)O[C@H](CO)[C@H]1O
Appearance: White to off-white crystalline powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 267.245 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Seifert R. Vidarabine is neither a potent nor a selective AC5 inhibitor. Biochem Pharmacol. 2014 Feb 15;87(4):543-6. doi: 10.1016/j.bcp.2013.12.025. Epub 2014 Jan 4. Review. PubMed PMID: 24398424.
2: Shen W, Kim JS, Mitchell S, Kish P, Kijek P, Hilfinger J. 5'-O-D-valyl ara A, a potential prodrug for improving oral bioavailability of the antiviral agent vidarabine. Nucleosides Nucleotides Nucleic Acids. 2009;28(1):43-55. doi: 10.1080/15257770802581757. PubMed PMID: 19116869; PubMed Central PMCID: PMC2642978.
3: Shen W, Kim JS, Kish PE, Zhang J, Mitchell S, Gentry BG, Breitenbach JM, Drach JC, Hilfinger J. Design and synthesis of vidarabine prodrugs as antiviral agents. Bioorg Med Chem Lett. 2009 Feb 1;19(3):792-6. doi: 10.1016/j.bmcl.2008.12.031. Epub 2008 Dec 10. PubMed PMID: 19097789; PubMed Central PMCID: PMC2642980.
4: Suzuki M, Okuda T, Shiraki K. Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus. Antiviral Res. 2006 Nov;72(2):157-61. Epub 2006 May 30. PubMed PMID: 16797734.
5: Miwa N, Kurosaki K, Yoshida Y, Kurokawa M, Saito S, Shiraki K. Comparative efficacy of acyclovir and vidarabine on the replication of varicella-zoster virus. Antiviral Res. 2005 Jan;65(1):49-55. PubMed PMID: 15652971.
6: Kurosaki K, Miwa N, Yoshida Y, Kurokawa M, Kurimoto M, Endo S, Shiraki K. Therapeutic basis of vidarabine on adenovirus-induced haemorrhagic cystitis. Antivir Chem Chemother. 2004 Sep;15(5):281-5. PubMed PMID: 15535050.
7: Hayashi K, Joko H, Koirala TR, Onoda S, Jin ZS, Munemasa M, Ohara N, Oda W, Tanaka T, Oka T, Kondo E, Yoshino T, Takahashi K, Yamada M, Akagi T. Therapeutic trials for a rabbit model of EBV-associated Hemophagocytic Syndrome (HPS): effects of vidarabine or CHOP, and development of Herpesvirus papio (HVP)-negative lymphomas surrounded by HVP-infected lymphoproliferative disease. Histol Histopathol. 2003 Oct;18(4):1155-68. PubMed PMID: 12973684.
8: Niwa K, Tagami K, Lian Z, Gao J, Mori H, Tamaya T. Topical vidarabine or 5-fluorouracil treatment against persistent HPV in genital (pre)cancerous lesions. Oncol Rep. 2003 Sep-Oct;10(5):1437-41. PubMed PMID: 12883720.
9: Kimura H, Morita M, Tsuge I, Hoshino Y, Tanaka N, Ito Y, Morishima T. Vidarabine therapy for severe chronic active Epstein-Barr virus infection. J Pediatr Hematol Oncol. 2001 Jun-Jul;23(5):294-9. PubMed PMID: 11464986.
10: Seabra C, Pérez-Simón JA, Sierra M, Marcos JM, Caballero MD, de la Loma A, Vazquez L, Del Cañizo MC, San Miguel JF. Intra-muscular vidarabine therapy for polyomavirus-associated hemorrhagic cystitis following allogeneic hemopoietic stem cell transplantation. Bone Marrow Transplant. 2000 Dec;26(11):1229-30. PubMed PMID: 11149737.
11: Honma Y, Niitsu N. Vidarabine and 2-deoxycoformycin as antileukemic agents against monocytic leukemia. Leuk Lymphoma. 2000 Sep;39(1-2):57-66. Review. PubMed PMID: 10975384.
12: Oh KW, Lee CK, Kim YS, Eo SK, Han SS. Antiherpetic activities of acidic protein bound polysacchride isolated from Ganoderma lucidum alone and in combinations with acyclovir and vidarabine. J Ethnopharmacol. 2000 Sep;72(1-2):221-7. PubMed PMID: 10967475.
13: Vianelli N, Renga M, Azzi A, De Santis RD, Bandini G, Tosi P, Tura S. Sequential vidarabine infusion in the treatment of polyoma virus-associated acute haemorrhagic cystitis late after allogeneic bone marrow transplantation. Bone Marrow Transplant. 2000 Feb;25(3):319-20. PubMed PMID: 10673705.
14: Okamoto A, Woodworth CD, Yen K, Chung J, Isonishi S, Nikaido T, Kiyokawa T, Seo H, Kitahara Y, Ochiai K, Tanaka T. Combination therapy with podophyllin and vidarabine for human papillomavirus positive cervical intraepithelial neoplasia. Oncol Rep. 1999 Mar-Apr;6(2):269-76. PubMed PMID: 10022988.
15: Kawakami M, Ueda S, Maeda T, Karasuno T, Teshima H, Hiraoka A, Nakamura H, Tanaka K, Masaoka T. Vidarabine therapy for virus-associated cystitis after allogeneic bone marrow transplantation. Bone Marrow Transplant. 1997 Sep;20(6):485-90. PubMed PMID: 9313882.
16: Durand M, Bost F, Maynard M, Baud M, Cohard M, Zarski JP. [Vidarabine-interferon combination in patients with chronic viral hepatitis B of mutant form. Efficiency and tolerability during a pilot study]. Presse Med. 1996 Mar 16;25(9):459. French. PubMed PMID: 8685199.
17: Kitabayashi A, Hirokawa M, Kuroki J, Nishinari T, Niitsu H, Miura AB. Successful vidarabine therapy for adenovirus type 11-associated acute hemorrhagic cystitis after allogeneic bone marrow transplantation. Bone Marrow Transplant. 1994 Nov;14(5):853-4. PubMed PMID: 7889020.
18: Stamminger T, Fleckenstein B. [Current developments in antiviral chemotherapy. 3: Vidarabine, ganciclovir]. Fortschr Med. 1994 Apr 30;112(12):172-3. German. PubMed PMID: 8200604.
19: Abghari SZ, Stulting RD, Zhu Z, Schinazi RF, Kaufman HE. Effect of genetically determined host factors on the efficacy of vidarabine, acyclovir and 5-trifluorothymidine in herpes simplex virus type 1 infection. Ophthalmic Res. 1994;26(2):95-104. PubMed PMID: 8196938.
20: Washio M, Hamada T, Goda H, Yoshimitsu T, Kajioka T, Koga H, Shogakiuchi Y, Fujishima M, Okayama M. Acyclovir-resistant herpes zoster encephalitis successfully treated with vidarabine: a case report. Fukuoka Igaku Zasshi. 1993 Oct;84(10):436-9. PubMed PMID: 8225157.
Related:
CAS#5536-17-4
CAS#24356-66-9 (hydrate).
