Pritelivir mesylate
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MedKoo CAT#: 330140

CAS#: 1428333-96-3 (mesylate)

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 mesylate
CAS# 1428333-96-3 (mesylate)

Theoretical Analysis

MedKoo Cat#: 330140
Name: Pritelivir mesylate
CAS#: 1428333-96-3 (mesylate)
Chemical Formula: C19H22N4O6S3
Exact Mass: 0.00
Molecular Weight: 498.587
Elemental Analysis: C, 45.77; H, 4.45; N, 11.24; O, 19.25; S, 19.29

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1650 Ready to ship
1g USD 2950 Ready to ship
2g USD 5250 Ready to ship
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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: Pritelivir mesylate, 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 mesylate

InChi Key: PPAJHCGEURRDOG-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H18N4O3S2.CH4O3S/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;1-5(2,3)4/h3-10H,11H2,1-2H3,(H2,19,24,25);1H3,(H,2,3,4)

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

Appearance: 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

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: Pritelivir mesylate is active against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) with the IC50 of 0.02 μM against HSV1-2.
In vitro activity: To mimic patient conditions during primary infection contrasting the prophylactic approach described, skin was first infected with HSV-1 for 4 days. Infected skin was further cultured with virus-free cell culture medium for 3 days in the presence or absence of pritelivir to measure its therapeutic potential. RT-PCR showed that pritelivir partly inhibited further replication by 62.3% compared with non–drug-treated, HSV-1–infected control (100%) (Figure 4e). Reference: J Invest Dermatol. 2019 Mar;139(3):673-682. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7100788/
In vivo activity: Mice lethally infected with HSV type 1 or 2 were treated 72 hours after infection for 7 days with pritelivir administered orally twice daily. Dosages of pritelivir from 0.3 to 30 mg/kg reduced mortality (P<0.001) against HSV-1, E-377. With an acyclovir resistant HSV-1, 11360, pritelivir at 1 and 3 mg/kg increased survival (P<0.005). With HSV-2, MS infected mice, all dosages higher than the 0.3 mg/kg dose of pritelivir were effective (P<0.005). These results suggest that pritelivir has potent and resistance-breaking antiviral efficacy with potential for the treatment of potentially life-threatening HSV type 1 and 2 infections, including herpes simplex encephalitis. Reference: Antiviral Res. 2018 Jan;149:1-6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5743594/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 83.3 167.13

Preparing Stock Solutions

The following data is based on the product molecular weight 498.59 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. 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. PMID: 27056950; PMCID: PMC4918824. 2. 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. PMID: 29113740; PMCID: PMC5743594. 3. 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. PMID: 24428466.
In vitro protocol: 1. 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. PMID: 27056950; PMCID: PMC4918824.
In vivo protocol: 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. PMID: 29113740; PMCID: PMC5743594. 2. 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. PMID: 24428466.

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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.