WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H328023
CAS#: 77181-69-2
Description: Sorivudine, also known as Bravavir; ARYS-01; BV-araU; BVAU; JA-001; SQ-32756; YN-72; DRU-0136, is a DNA polymerase inhibitor potentially for the treatment of herpes zoster (shingles). Sorivudine: a promising drug for the treatment of varicella-zoster virus infection. Sorivudine provides a unique nucleoside analog with significantly enhanced both in vitro as in vitro activity toward VZV and enhanced oral bioavailability, as compared with existing antivirals.
Hodoodo Cat#: H328023
Name: Sorivudine
CAS#: 77181-69-2
Chemical Formula: C11H13BrN2O6
Exact Mass: 348.00
Molecular Weight: 349.137
Elemental Analysis: C, 37.84; H, 3.75; Br, 22.89; N, 8.02; O, 27.49
Synonym: Sorivudine; Bravavir; ARYS-01; BV-araU; BVAU; JA-001; SQ-32756; YN-72; ARYS01; JA001; SQ32756; YN72; DRU0136; DRU-0136.
IUPAC/Chemical Name: 5-((E)-2-bromovinyl)-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
InChi Key: GCQYYIHYQMVWLT-HQNLTJAPSA-N
InChi Code: InChI=1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1
SMILES Code: O=C1NC(C(/C=C/Br)=CN1[C@H]2[C@H]([C@@H]([C@@H](CO)O2)O)O)=O
Appearance: Solid powder
Purity: >95% (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
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
More Info:
| Biological target: | Sorivudine is a synthetic pyrimidine nucleoside antimetabolite drug that derives its antiviral activity from selective conversion by a specific thymidine kinase present in certain DNA viruses to nucleotides. |
| In vitro activity: | The EC50s of sorivudine for varicella-zoster virus increased as the time of treatment was delayed from 6 to 18 h after infection. Susceptibility of infected cells at 0 and 18 h after infection was examined with four anti-herpes drugs, and the fold increases in EC50 for sorivudine was 6.3. Reference: Antiviral Res. 2020 Aug;180:104829. https://pubmed.ncbi.nlm.nih.gov/32569704/ |
| In vivo activity: | Sorivudine reduced the mortality rates of mice infected with herpes simplex virus type 1. The degree of efficacy of sorivudine was equivalent to that of acyclovir in 4-week-old CYP mice infected with the less virulent herpes strain. Sorivudine (20 mg/kg) suppressed viral growth in various organs of cyclophosphamide-treated, immunosuppressed mice. Reference: Antimicrob Agents Chemother. 1990 Dec;34(12):2431-3. https://pubmed.ncbi.nlm.nih.gov/1965108/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 250.0 | 716.07 |
The following data is based on the product molecular weight 349.14 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 |
| Formulation protocol: | 1. Shiraki K, Tan L, Daikoku T, Takemoto M, Sato N, Yoshida Y. Viral ribonucleotide reductase attenuates the anti-herpes activity of acyclovir in contrast to amenamevir. Antiviral Res. 2020 Aug;180:104829. doi: 10.1016/j.antiviral.2020.104829. Epub 2020 Jun 20. PMID: 32569704. 2. Machida H, Nishitani M, Suzutani T, Hayashi K. Different antiviral potencies of BV-araU and related nucleoside analogues against herpes simplex virus type 1 in human cell lines and Vero cells. Microbiol Immunol. 1991;35(11):963-73. doi: 10.1111/j.1348-0421.1991.tb01618.x. PMID: 1663576. 3. Kanamitsu SI, Ito K, Okuda H, Ogura K, Watabe T, Muro K, Sugiyama Y. Prediction of in vivo drug-drug interactions based on mechanism-based inhibition from in vitro data: inhibition of 5-fluorouracil metabolism by (E)-5-(2-Bromovinyl)uracil. Drug Metab Dispos. 2000 Apr;28(4):467-74. PMID: 10725316. 4. Ijichi K, Ashida N, Machida H. Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus type 1 infection in immunosuppressed mice. Antimicrob Agents Chemother. 1990 Dec;34(12):2431-3. doi: 10.1128/AAC.34.12.2431. PMID: 1965108; PMCID: PMC172077. |
| In vitro protocol: | 1. Shiraki K, Tan L, Daikoku T, Takemoto M, Sato N, Yoshida Y. Viral ribonucleotide reductase attenuates the anti-herpes activity of acyclovir in contrast to amenamevir. Antiviral Res. 2020 Aug;180:104829. doi: 10.1016/j.antiviral.2020.104829. Epub 2020 Jun 20. PMID: 32569704. 2. Machida H, Nishitani M, Suzutani T, Hayashi K. Different antiviral potencies of BV-araU and related nucleoside analogues against herpes simplex virus type 1 in human cell lines and Vero cells. Microbiol Immunol. 1991;35(11):963-73. doi: 10.1111/j.1348-0421.1991.tb01618.x. PMID: 1663576. |
| In vivo protocol: | 1. Kanamitsu SI, Ito K, Okuda H, Ogura K, Watabe T, Muro K, Sugiyama Y. Prediction of in vivo drug-drug interactions based on mechanism-based inhibition from in vitro data: inhibition of 5-fluorouracil metabolism by (E)-5-(2-Bromovinyl)uracil. Drug Metab Dispos. 2000 Apr;28(4):467-74. PMID: 10725316. 2. Ijichi K, Ashida N, Machida H. Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus type 1 infection in immunosuppressed mice. Antimicrob Agents Chemother. 1990 Dec;34(12):2431-3. doi: 10.1128/AAC.34.12.2431. PMID: 1965108; PMCID: PMC172077. |
1: Watabe T, Ogura K, Nishiyama T. [Molecular toxicological mechanism of the lethal interactions of the new antiviral drug, sorivudine, with 5-fluorouracil prodrugs and genetic deficiency of dihydropyrimidine dehydrogenase]. Yakugaku Zasshi. 2002 Aug;122(8):527-35. Review. Japanese. PubMed PMID: 12187768.
2: Desai D, Li D, Janjikhel R, Lang B, Jain N. Effects of light intensity, n-alcohols, water-soluble colorants, and solution viscosity on photoisomerization of sorivudine. Pharm Dev Technol. 2001;6(1):99-106. PubMed PMID: 11247280.
3: Rosenthal G, Bartz-Schmidt KU, Walter P, Kirchhof B, Heimann K. Failure of sorivudine therapy in progressive outer retinal necrosis caused by varicella zoster virus. Aust N Z J Ophthalmol. 1998 Nov;26(4):327-8. PubMed PMID: 9843261.
4: Okuda H, Ogura K, Kato A, Takubo H, Watabe T. A possible mechanism of eighteen patient deaths caused by interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs. J Pharmacol Exp Ther. 1998 Nov;287(2):791-9. PubMed PMID: 9808711.
5: Diasio RB. Sorivudine and 5-fluorouracil; a clinically significant drug-drug interaction due to inhibition of dihydropyrimidine dehydrogenase. Br J Clin Pharmacol. 1998 Jul;46(1):1-4. PubMed PMID: 9690942; PubMed Central PMCID: PMC1873978.
6: Gnann JW Jr, Crumpacker CS, Lalezari JP, Smith JA, Tyring SK, Baum KF, Borucki MJ, Joseph WP, Mertz GJ, Steigbigel RT, Cloud GA, Soong SJ, Sherrill LC, DeHertogh DA, Whitley RJ. Sorivudine versus acyclovir for treatment of dermatomal herpes zoster in human immunodeficiency virus-infected patients: results from a randomized, controlled clinical trial. Collaborative Antiviral Study Group/AIDS Clinical Trials Group, Herpes Zoster Study Group. Antimicrob Agents Chemother. 1998 May;42(5):1139-45. PubMed PMID: 9593141; PubMed Central PMCID: PMC105759.
7: Ogura K, Nishiyama T, Takubo H, Kato A, Okuda H, Arakawa K, Fukushima M, Nagayama S, Kawaguchi Y, Watabe T. Suicidal inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil derived from the antiviral, sorivudine. Cancer Lett. 1998 Jan 9;122(1-2):107-13. Erratum in: Cancer Lett 1998 Jun 19;128(2):229. PubMed PMID: 9464498.
8: Watabe T, Okuda H, Ogura K. [Lethal drug interactions of the new antiviral, sorivudine, with anticancer prodrugs of 5-fluorouracil]. Yakugaku Zasshi. 1997 Nov;117(10-11):910-21. Review. Japanese. PubMed PMID: 9414600.
9: Bodsworth NJ, Boag F, Burdge D, Généreux M, Borleffs JC, Evans BA, Modai J, Colebunders R, Thomas M, DeHertogh D, Pacelli L, Thomis J. Evaluation of sorivudine (BV-araU) versus acyclovir in the treatment of acute localized herpes zoster in human immunodeficiency virus-infected adults. The Multinational Sorivudine Study Group. J Infect Dis. 1997 Jul;176(1):103-11. PubMed PMID: 9207355.
10: Yan J, Tyring SK, McCrary MM, Lee PC, Haworth S, Raymond R, Olsen SJ, Diasio RB. The effect of sorivudine on dihydropyrimidine dehydrogenase activity in patients with acute herpes zoster. Clin Pharmacol Ther. 1997 May;61(5):563-73. PubMed PMID: 9164418.
11: Okuda H, Nishiyama T, Ogura K, Nagayama S, Ikeda K, Yamaguchi S, Nakamura Y, Kawaguchi Y, Watabe T. Lethal drug interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs. Drug Metab Dispos. 1997 May;25(5):270-3. PubMed PMID: 9152608.
12: Nakayama H, Kinouchi T, Kataoka K, Akimoto S, Matsuda Y, Ohnishi Y. Intestinal anaerobic bacteria hydrolyse sorivudine, producing the high blood concentration of 5-(E)-(2-bromovinyl)uracil that increases the level and toxicity of 5-fluorouracil. Pharmacogenetics. 1997 Feb;7(1):35-43. PubMed PMID: 9110360.
13: Okuda H, Nishiyama T, Ogura K, Nagayama S, Ikeda K, Yamaguchi S, Nakamura Y, Kawaguchi K, Watabe T, Ogura Y. Lethal drug interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs. Drug Metab Dispos. 1997 Feb;25(2):270-3. Corrected and republished in: Drug Metab Dispos. 1997 May;25(5):270-3. PubMed PMID: 9029059.
14: Watabe T. Strategic proposals for predicting drug-drug interactions during new drug development: based on sixteen deaths caused by interactions of the new antiviral sorivudine with 5-fluorouracil prodrugs. J Toxicol Sci. 1996 Dec;21(5):299-300. PubMed PMID: 9035040.
15: Wallace MR, Chamberlin CJ, Sawyer MH, Arvin AM, Harkins J, LaRocco A, Colopy MW, Bowler WA, Oldfield EC 3rd. Treatment of adult varicella with sorivudine: a randomized, placebo-controlled trial. J Infect Dis. 1996 Aug;174(2):249-55. PubMed PMID: 8699051.
16: Wunderli W, Miner R, Wintsch J, von Gunten S, Hirsch HH, Hirschel B. Outer retinal necrosis due to a strain of varicella-zoster virus resistant to acyclovir, ganciclovir, and sorivudine. Clin Infect Dis. 1996 May;22(5):864-5. PubMed PMID: 8722954.
17: Miyauchi S, Imaoka T, Okada T, Motoyama M, Kawaguchi T, Akiyama H, Odomi M. Leukopenia-inducing effect of a combination of a new 5-fluorouracil (5-FU)-derived drug, BOF-A2 (emitefur), with other 5-FU-derived drugs or BV-araU (sorivudine) in rats. Jpn J Pharmacol. 1996 Feb;70(2):139-48. PubMed PMID: 8866751.
18: Whitley RJ. Sorivudine: a potent inhibitor of varicella zoster virus replication. Adv Exp Med Biol. 1996;394:41-4. Review. PubMed PMID: 8815706.
19: Whitley RJ. Sorivudine: a promising drug for the treatment of varicella-zoster virus infection. Neurology. 1995 Dec;45(12 Suppl 8):S73-5. Review. PubMed PMID: 8545030.
20: Sato H, Oh H, Cho R, Nakamura H, Asai T. Successful treatment of sorivudine-related agranulocytosis with granulocyte-colony stimulating factor. Am J Hematol. 1995 Nov;50(3):227. PubMed PMID: 7485091.
