MedKoo Cat#: 510252 | Name: Pritelivir
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Description:

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

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

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: 402.0820

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
25mg USD 110.00 Ready to ship
50mg USD 180.00 Ready to ship
100mg USD 320.00 Ready to ship
200mg USD 550.00 Ready to ship
500mg USD 1,250.00 Ready to ship
1g USD 2,250.00 Ready to ship
2g USD 4,050.00 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
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
More Info
         
Biological target:
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/
Solvent mg/mL mM comments
Solubility
DSMO 56.5 140.38
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 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
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.
1: Sassine J, Siegrist EA, Shafat TF, Chemaly RF. Advances and prospect in herpesviruses infections after haematopoietic cell transplantation: closer to the finish line? Clin Microbiol Infect. 2024 Jun 28:S1198-743X(24)00300-8. doi: 10.1016/j.cmi.2024.06.020. Epub ahead of print. PMID: 38945270. 2: Normand C, Thieulent CJ, Fortier C, Sutton G, Senamaud-Beaufort C, Jourdren L, Blugeon C, Vidalain PO, Pronost S, Hue ES. A Screening Study Identified Decitabine as an Inhibitor of Equid Herpesvirus 4 That Enhances the Innate Antiviral Response. Viruses. 2024 May 8;16(5):746. doi: 10.3390/v16050746. PMID: 38793627; PMCID: PMC11125953. 3: de Vries M, Bonsmann S, Pausch J, Sumner M, Birkmann A, Zimmermann H, Kropeit D. Evaluation of the Clinical Drug-Drug Interaction Potential of Pritelivir on Transporters and CYP450 Enzymes Using a Cocktail Approach. Clin Pharmacol Drug Dev. 2024 Jul;13(7):755-769. doi: 10.1002/cpdd.1408. Epub 2024 May 16. PMID: 38752475. 4: Wang X, Patrikeeva S, Nanovskaya T, Bryant V. Development and validation of HPLC-ultraviolet method for quantitative determination of pritelivir in human placental perfusion medium. Biomed Chromatogr. 2024 Jul;38(7):e5888. doi: 10.1002/bmc.5888. Epub 2024 May 10. PMID: 38727008; PMCID: PMC11262560. 5: Gege C, Kleymann G. Replacement of sulfonamide by sulfoximine within a helicase-primase inhibitor with restricted flexibility. Bioorg Med Chem Lett. 2024 Jul 1;106:129761. doi: 10.1016/j.bmcl.2024.129761. Epub 2024 Apr 19. PMID: 38642810. 6: Bonsmann S, McCormick D, Pausch J, de Vries M, Sumner M, Birkmann A, Zimmermann H, Kropeit D. Mass Balance and Metabolite Profile after Single and Multiple Oral Doses of Pritelivir in Healthy Subjects. Clin Pharmacol Drug Dev. 2024 Apr;13(4):389-403. doi: 10.1002/cpdd.1358. Epub 2024 Jan 8. PMID: 38189209. 7: Srinivasan K, Ho DY. Case Commentary: "Salvage Treatment of Refractory HSV Oral Lesions with Pritelivir in Allogeneic Hematopoietic Cell Transplant Recipients" by Bosetti et al. Antimicrob Agents Chemother. 2023 May 17;67(5):e0027623. doi: 10.1128/aac.00276-23. Epub 2023 Apr 4. PMID: 37014226; PMCID: PMC10190666. 8: Bosetti D, Bernardi C, Maulini M, Giannotti F, Mamez AC, Masouridi-Levrat S, Chalandon Y, Neofytos D. Salvage Treatment of Refractory HSV Oral Lesions with Pritelivir in Allogeneic Hematopoietic Cell Transplant Recipients. Antimicrob Agents Chemother. 2023 Apr 18;67(4):e0173222. doi: 10.1128/aac.01732-22. Epub 2023 Mar 27. PMID: 36971558; PMCID: PMC10112206. 9: Kropeit D, Bonsmann S, von Richter O, McCormick D, Pausch J, Sumner M, Birkmann A, Zimmermann H, Rübsamen-Schaeff H. First-in-Human, Single- and Multiple-Ascending-Dose, Food-Effect, and Absolute Bioavailability Trials to Assess the Pharmacokinetics, Safety, and Tolerability of Pritelivir, a Nonnucleoside Helicase-Primase Inhibitor Against Herpes Simplex Virus in Healthy Subjects. Clin Pharmacol Drug Dev. 2023 Jul;12(7):749-760. doi: 10.1002/cpdd.1241. Epub 2023 Mar 1. PMID: 36860173. 10: Kotton BD, Kotton CN. Resistant herpes simplex virus infections - who, when, and what's new? Curr Opin Infect Dis. 2022 Dec 1;35(6):530-535. doi: 10.1097/QCO.0000000000000889. Epub 2022 Oct 7. PMID: 36206151. 11: Birkmann A, Bonsmann S, Kropeit D, Pfaff T, Rangaraju M, Sumner M, Timmler B, Zimmermann H, Buschmann H, Ruebsamen-Schaeff H. Discovery, Chemistry, and Preclinical Development of Pritelivir, a Novel Treatment Option for Acyclovir- Resistant Herpes Simplex Virus Infections. J Med Chem. 2022 Oct 27;65(20):13614-13628. doi: 10.1021/acs.jmedchem.2c00668. Epub 2022 Oct 6. PMID: 36202389; PMCID: PMC9620171. 12: Gege C, Kleymann G. Helicase-primase inhibitors from Medshine Discovery Inc. (WO2018/127207 and WO2020/007355) for the treatment of herpes simplex virus infections - structure proposal for Phaeno Therapeutics drug candidate HN0037. Expert Opin Ther Pat. 2022 Sep;32(9):933-937. doi: 10.1080/13543776.2022.2113873. Epub 2022 Aug 19. PMID: 35965439. 13: Serris A, Pouvaret A, Loiseau C, Abid H, Burrel S, Fourgeaud J, Rouzaud C, Lanternier F, Boutolleau D, Frange P. Pritelivir for recurrent aciclovir- resistant herpes simplex virus 2 infections in immunocompromised patients. J Antimicrob Chemother. 2022 Jul 28;77(8):2303-2305. doi: 10.1093/jac/dkac165. PMID: 35639560. 14: Spahn S, Riessen R, Berg CP, Malek NP, Emrich MH, Lohrengel K, Ganzenmueller T, Iftner T, Kleymann G, Hamprecht K. Comprehensive clinical and virological characterization of three cases of fulminant liver failure owing to HSV1 primary infection. Liver Int. 2022 May;42(5):1005-1011. doi: 10.1111/liv.15215. Epub 2022 Mar 7. PMID: 35230726. 15: Nandi R, Bhowmik D, Srivastava R, Prakash A, Kumar D. Discovering potential inhibitors against SARS-CoV-2 by targeting Nsp13 Helicase. J Biomol Struct Dyn. 2022;40(22):12062-12074. doi: 10.1080/07391102.2021.1970024. Epub 2021 Aug 28. PMID: 34455933. 16: Shiraki K, Yasumoto S, Toyama N, Fukuda H. Amenamevir, a Helicase-Primase Inhibitor, for the Optimal Treatment of Herpes Zoster. Viruses. 2021 Aug 5;13(8):1547. doi: 10.3390/v13081547. PMID: 34452412; PMCID: PMC8402822. 17: Schultz A, Knoll T, Urban A, Schuck H, von Briesen H, Germann A, Velten T. Novel Cost-Efficient Graphene-Based Impedance Biosensor for the Analysis of Viral Cytopathogenicity and the Effect of Antiviral Drugs. Front Bioeng Biotechnol. 2021 Jul 26;9:718889. doi: 10.3389/fbioe.2021.718889. PMID: 34381768; PMCID: PMC8350578. 18: Cannon L, Tholouli E, Ward C, Farooq H, Kingston M. Use of pritelivir in refractory aciclovir-resistant herpes simplex virus type 2. Int J STD AIDS. 2021 Sep;32(10):978-980. doi: 10.1177/09564624211006568. Epub 2021 May 4. PMID: 33947276. 19: Thieulent C, Hue ES, Sutton G, Fortier C, Dallemagne P, Zientara S, Munier- Lehmann H, Hans A, Paillot R, Vidalain PO, Pronost S. Identification of antiviral compounds against equid herpesvirus-1 using real-time cell assay screening: Efficacy of decitabine and valganciclovir alone or in combination. Antiviral Res. 2020 Nov;183:104931. doi: 10.1016/j.antiviral.2020.104931. Epub 2020 Sep 11. PMID: 32926887. 20: Ruebsamen-Schaeff H, Buschmann H. Different solid forms for optimizing route of administration of the herpes drug Pritelivir. Medchemcomm. 2019 Aug 9;10(11):1867-1870. doi: 10.1039/c9md00233b. PMID: 32346467; PMCID: PMC7161071.