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MedKoo Cat#: 328023 | Name: Sorivudine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Sorivudine
Sorivudine
CAS#77181-69-2

Theoretical Analysis

MedKoo Cat#: 328023

Name: Sorivudine

CAS#: 77181-69-2

Chemical Formula: C11H13BrN2O6

Exact Mass: 347.9957

Molecular Weight: 349.14

Elemental Analysis: C, 37.84; H, 3.75; Br, 22.89; N, 8.02; O, 27.49

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,250.00 Ready to ship
200mg USD 1,950.00 Ready to ship
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Related CAS #
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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 mg/mL mM comments
Solubility
DMSO 250.0 716.07
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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: Manolopoulos VG, Ragia G. Fluoropyrimidine Toxicity: the Hidden Secrets of DPYD. Curr Drug Metab. 2024;25(2):91-95. doi: 10.2174/0113892002296707240311105527. PMID: 38504562. 2: Rahman MR, Banik A, Chowdhury IM, Sajib EH, Sarkar S. Identification of potential antivirals against SARS-CoV-2 using virtual screening method. Inform Med Unlocked. 2021;23:100531. doi: 10.1016/j.imu.2021.100531. Epub 2021 Feb 10. PMID: 33594342; PMCID: PMC7874919. 3: 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. 4: Burke MP, Borland KM, Litosh VA. Base-Modified Nucleosides as Chemotherapeutic Agents: Past and Future. Curr Top Med Chem. 2016;16(11):1231-41. doi: 10.2174/1568026615666150915111933. PMID: 26369814. 5: Klaassen CD, Cui JY. Review: Mechanisms of How the Intestinal Microbiota Alters the Effects of Drugs and Bile Acids. Drug Metab Dispos. 2015 Oct;43(10):1505-21. doi: 10.1124/dmd.115.065698. Epub 2015 Aug 10. PMID: 26261286; PMCID: PMC4576672. 6: Coen N, Duraffour S, Topalis D, Snoeck R, Andrei G. Spectrum of activity and mechanisms of resistance of various nucleoside derivatives against gammaherpesviruses. Antimicrob Agents Chemother. 2014 Dec;58(12):7312-23. doi: 10.1128/AAC.03957-14. Epub 2014 Sep 29. PMID: 25267682; PMCID: PMC4249563. 7: Wang LX, Takayama-Ito M, Kinoshita-Yamaguchi H, Kakiuchi S, Suzutani T, Nakamichi K, Lim CK, Kurane I, Saijo M. Characterization of DNA polymerase- associated acyclovir-resistant herpes simplex virus type 1: mutations, sensitivity to antiviral compounds, neurovirulence, and in-vivo sensitivity to treatment. Jpn J Infect Dis. 2013;66(5):404-10. doi: 10.7883/yoken.66.404. PMID: 24047739. 8: Li-Wan-Po A. The human genome: its modifications and interactions with those of the microbiome, and the practice of genomic medicine. Discov Med. 2013 May;15(84):283-90. PMID: 23725601. 9: Andrei G, Topalis D, Fiten P, McGuigan C, Balzarini J, Opdenakker G, Snoeck R. In vitro-selected drug-resistant varicella-zoster virus mutants in the thymidine kinase and DNA polymerase genes yield novel phenotype-genotype associations and highlight differences between antiherpesvirus drugs. J Virol. 2012 Mar;86(5):2641-52. doi: 10.1128/JVI.06620-11. Epub 2011 Dec 21. PMID: 22190713; PMCID: PMC3302250. 10: Satyaprakash AK, Tremaine AM, Stelter AA, Creed R, Ravanfar P, Mendoza N, Mehta SK, Rady PL, Pierson DL, Tyring SK. Viremia in acute herpes zoster. J Infect Dis. 2009 Jul 1;200(1):26-32. doi: 10.1086/599381. PMID: 19469706. 11: Takahashi H. [The history of adverse drug reactions, relief for these health damage and safety measures in Japan]. Yakushigaku Zasshi. 2009;44(2):64-70. Japanese. PMID: 20527311. 12: Watanabe S, Misu T, Kurihara T, Suzuki S, Sakurada T, Satoh N, Ueda S. Regulation of the statements in the information on drug metabolizing enzyme in the package insert--the present regulation and its history in Japan, the U.S. and the U.K. Yakushigaku Zasshi. 2008;43(2):175-80. PMID: 19579828. 13: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 May;29(4):303-11. PMID: 17609744. 14: Yoshikawa S, Satou K, Konagaya A. Drug interaction ontology (DIO) for inferences of possible drug-drug interactions. Stud Health Technol Inform. 2004;107(Pt 1):454-8. PMID: 15360854. 15: Beijnen JH, Schellens JH. Drug interactions in oncology. Lancet Oncol. 2004 Aug;5(8):489-96. doi: 10.1016/S1470-2045(04)01528-1. PMID: 15288238. 16: Andrei G, De Clercq E, Snoeck R. In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir? Antiviral Res. 2004 Mar;61(3):181-7. doi: 10.1016/j.antiviral.2003.10.003. PMID: 15168799. 17: 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. Japanese. doi: 10.1248/yakushi.122.527. PMID: 12187768. 18: Ozawa S. [Drug-drug interaction in pharmacogenetics and pharmacogenomics]. Rinsho Byori. 2002 Feb;50(2):146-50. Japanese. PMID: 11925851. 19: Naesens L, De Clercq E. Recent developments in herpesvirus therapy. Herpes. 2001 Mar;8(1):12-6. PMID: 11867011. 20: Balzarinia J, Degrève B, Zhu C, Durini E, Porcu L, De Clercq E, Karlsson A, Manfredini S. 2'-O-Acyl/alkyl-substituted arabinosyl nucleosides as inhibitors of human mitochondrial thymidine kinase. Biochem Pharmacol. 2001 Mar 15;61(6):727-32. doi: 10.1016/s0006-2952(01)00529-9. PMID: 11266658.