Pritelivir
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MedKoo CAT#: 510252

CAS#: 348086-71-5 (free base)

Description: Pritelivir, also known as AIC-316 and BAY 57-1293, is a potent helicase primase inhibitor. BAY 57-1293 inhibits replication of herpes simplex virus (HSV) type 1 and type 2 in the nanomolar range in vitro by abrogating the enzymatic activity of the viral primase-helicase complex. In various rodent models of HSV infection the antiviral activity of BAY 57-1293 in vivo was found to be superior compared to all compounds currently used to treat HSV infections. The compound shows profound antiviral activity in murine and rat lethal challenge models of disseminated herpes, in a murine zosteriform spread model of cutaneous disease, and in a murine ocular herpes model. It is active in parenteral, oral, and topical formulations.


Chemical Structure

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Pritelivir
CAS# 348086-71-5 (free base)

Theoretical Analysis

MedKoo Cat#: 510252
Name: Pritelivir
CAS#: 348086-71-5 (free base)
Chemical Formula: C18H18N4O3S2
Exact Mass: 402.08203
Molecular Weight: 402.49
Elemental Analysis: C, 53.71; H, 4.51; N, 13.92; O, 11.93; S, 15.93

Price and Availability

Size Price Availability Quantity
50.0mg USD 150.0 Same day
100.0mg USD 250.0 Same day
200.0mg USD 450.0 Same day
500.0mg USD 850.0 Same day
1.0g USD 1350.0 Same day
2.0g USD 2150.0 Same day
5.0g USD 3850.0 Same day
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Related CAS #: 1428333-96-3 (mseylate)   348086-71-5 (free base)   910864-57-2 (HCl)   910864-61-8 (besylate)   2088209-68-9 (sulfate)    

Synonym: BAY57-1293; BAY 57-1293; BAY-57-1293; BAY571293; BAY 571293; BAY-571293; AIC-316; AIC 316; AIC316; Pritelivir.

IUPAC/Chemical Name: N-methyl-N-(4-methyl-5-sulfamoylthiazol-2-yl)-2-(4-(pyridin-2-yl)phenyl)acetamide

InChi Key: IVZKZONQVYTCKC-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H18N4O3S2/c1-12-17(27(19,24)25)26-18(21-12)22(2)16(23)11-13-6-8-14(9-7-13)15-5-3-4-10-20-15/h3-10H,11H2,1-2H3,(H2,19,24,25)

SMILES Code: O=C(N(C)C1=NC(C)=C(S(=O)(N)=O)S1)CC2=CC=C(C3=NC=CC=C3)C=C2

Appearance: white solid 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

Preparing Stock Solutions

The following data is based on the product molecular weight 402.49 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

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1: Quenelle DC, Birkmann A, Goldner T, Pfaff T, Zimmermann H, Bonsmann S, Collins DJ, Rice TL, Prichard MN. Efficacy of pritelivir and acyclovir in the treatment of herpes simplex virus infections in a mouse model of herpes simplex encephalitis. Antiviral Res. 2018 Jan;149:1-6. doi: 10.1016/j.antiviral.2017.11.002. Epub 2017 Nov 4. PubMed PMID: 29113740; PubMed Central PMCID: PMC5743594.

2: Wald A, Timmler B, Magaret A, Warren T, Tyring S, Johnston C, Fife K, Selke S, Huang ML, Stobernack HP, Zimmermann H, Corey L, Birkmann A, Ruebsamen-Schaeff H. Effect of Pritelivir Compared With Valacyclovir on Genital HSV-2 Shedding in Patients With Frequent Recurrences: A Randomized Clinical Trial. JAMA. 2016 Dec 20;316(23):2495-2503. doi: 10.1001/jama.2016.18189. Erratum in: JAMA. 2017 Feb 14;317(6):648. PubMed PMID: 27997653.

3: Edlefsen PT, Birkmann A, Huang ML, Magaret CA, Kee JJ, Diem K, Goldner T, Timmler B, Stoelben S, Ruebsamen-Schaeff H, Zimmermann H, Warren T, Wald A, Corey L. No Evidence of Pritelivir Resistance Among Herpes Simplex Virus Type 2 Isolates After 4 Weeks of Daily Therapy. J Infect Dis. 2016 Jul 15;214(2):258-64. doi: 10.1093/infdis/jiw129. Epub 2016 Apr 7. PubMed PMID: 27056950; PubMed Central PMCID: PMC4918824.

4: Schiffer JT, Swan DA, Magaret A, Corey L, Wald A, Ossig J, Ruebsamen-Schaeff H, Stoelben S, Timmler B, Zimmermann H, Melhem MR, Van Wart SA, Rubino CM, Birkmann A. Mathematical modeling of herpes simplex virus-2 suppression with pritelivir predicts trial outcomes. Sci Transl Med. 2016 Feb 3;8(324):324ra15. doi: 10.1126/scitranslmed.aad6654. PubMed PMID: 26843190; PubMed Central PMCID: PMC4880060.

5: Burrel S, Rouard C, Boutolleau D. Helicase-primase inhibitor pritelivir for HSV-2 infection. N Engl J Med. 2014 Apr 24;370(17):1663-4. doi: 10.1056/NEJMc1402071. PubMed PMID: 24758629.

6: Biswas S, Sukla S, Goldner T, Field HJ, Kropeit D, Paulsen D, Welbers A, Ruebsamen-Schaeff H, Zimmermann H, Birkmann A. Pharmacokinetics-pharmacodynamics of the helicase-primase inhibitor pritelivir following treatment of wild-type or pritelivir-resistant virus infection in a murine herpes simplex virus 1 infection model. Antimicrob Agents Chemother. 2014 Jul;58(7):3843-52. doi: 10.1128/AAC.02641-14. Epub 2014 Apr 21. PubMed PMID: 24752278; PubMed Central PMCID: PMC4068558.

7: Wald A, Corey L, Timmler B, Magaret A, Warren T, Tyring S, Johnston C, Kriesel J, Fife K, Galitz L, Stoelben S, Huang ML, Selke S, Stobernack HP, Ruebsamen-Schaeff H, Birkmann A. Helicase-primase inhibitor pritelivir for HSV-2 infection. N Engl J Med. 2014 Jan 16;370(3):201-10. doi: 10.1056/NEJMoa1301150. PubMed PMID: 24428466.

8: Field HJ, Huang ML, Lay EM, Mickleburgh I, Zimmermann H, Birkmann A. Baseline sensitivity of HSV-1 and HSV-2 clinical isolates and defined acyclovir-resistant strains to the helicase-primase inhibitor pritelivir. Antiviral Res. 2013 Nov;100(2):297-9. doi: 10.1016/j.antiviral.2013.08.024. Epub 2013 Sep 8. PubMed PMID: 24021190.



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