Pritelivir mesylate

CAS
1428333-96-3
Catalog Number
ACM1428333963
Category
Inhibitors
Molecular Weight
498.59
Molecular Formula
C19H22N4O6S3

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Specification

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.
Synonyms
Pritelivir mesylate, BAY57-1293; BAY 57-1293; BAY-57-1293; BAY571293; BAY 571293; BAY-571293; AIC-316; AIC 316; AIC316
IUPAC Name
N-methyl-N-(4-methyl-5-sulfamoylthiazol-2-yl)-2-(4-(pyridin-2-yl)phenyl)acetamide mesylate
Canonical SMILES
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
InChI
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)
InChI Key
PPAJHCGEURRDOG-UHFFFAOYSA-N
Solubility
Soluble in DMSO
Appearance
Solid powder
Shelf Life
>2 years if stored properly
Storage
Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
Alternative CAS
1428333-96-3 (mseylate); 348086-71-5 (free base); 910864-57-2 (HCl); 910864-61-8 (besylate); 2088209-68-9 (sulfate)
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.
Drug Formulation
This drug may be formulated in DMSO
Elemental Analysis
C, 45.77; H, 4.45; N, 11.24; O, 19.25; S, 19.29
Exact Mass
498.0701
HS Tariff Code
2934.99.9001
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/
Shipping
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.
Stock Solution Storage
0-4 °C for short term (days to weeks), or -20 °C for long term (months).
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