Products for Research Use Only

Glecaprevir

CAT: 0013-GTR19163731-02Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19163731-02Size:500 mg
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Description
Glecaprevir (ABT 493; A 1282576) is a novel HCV NS3/4A protease inhibitor with pan-genotypic activity, inhibits NS3/4A proteases from HCV genotypes 1-6 in vitro with IC50 of 3.5-11.3 nM; inhibits the replication of stable HCV subgenomic replicons genotypes 1-6 with EC50 of 0.21-4.6 nM, has a median EC50 of 0.30 nM (0.05 - 3.8 nM) for HCV replicons containing proteases from 40 HCV genotype 1-5 samples; the combination of ABT-493 and ABT-530 demonstrates potent antiviral activity and acceptable safety in clinical trails with HCV genotype 1 infection.HCV Infection Phase 2 Clinical (In Vitro) :Glecaprevir inhibits the enzymatic activity of HCV genotype 1-6 NS3/4A proteases with half maximal inhibitory concentration (IC50) values ranging from 3.5 to 11.3 nM in a biochemical assay. Glecaprevir inhibites HCV subgenomic stable replicons containing proteases from HCV genotypes 1a, 1b, 2a, 2b, 3a, 4a, 5a, 6a and 6e in Huh-7 cells with 50% effective concentration (EC50) values ranging from 0.21 to 4.6 nM. Glecaprevir is active against a replicon containing protease from genotype 3, the most difficult-to-treat HCV genotype, with an EC50 value of 1.9 nM, which is 10- and 44-fold lower than those for paritaprevir and grazoprevir, respectively. The median Glecaprevir EC50 values against replicons containing these genotype 1a, 1b, 2a, 2b, 3a, 4a, 4d, and 5a clinical samples are 0.08, 0.29, 1.6, 2.2, 2.3, 0.41, 0.17, and 0.12 nM, respectively, with an overall median EC50 value of 0.30 nM (range=0.05~3.8 nM) .
CAS Number
1365970-03-1
Product Name Alternative
ABT 493 | A 1282576
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: 80 mg/mL (< 1 mg/ml refers to the product slightly soluble or insoluble)
Smiles
CC1 (CC1) S (=O) (=O) NC (=O) C2 (CC2C (F) F) NC (=O) C3CC4CN3C (=O) C (NC (=O) OC5CCCC5OCC=CC (C6=NC7=CC=CC=C7N=C6O4) (F) F) C (C) (C) C
Molecular Formula
C38H46F4N6O9S
Molecular Weight
838.87
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(33R,35S,91R,92R,5S, E) -5- (tert-butyl) -N- ((1R,2R) -2- (difluoromethyl) -1- (((1-methylcyclopropyl) sulfonyl) carbamoyl) cyclopropyl) -14,14-difluoro-4,7-dioxo-2,8,10-trioxa-6-aza-1 (2,3) -quinoxalina-3 (3,1) -pyrrolidina-9 (1,2) -cyclopentanacyclotetradecaphan-12-ene-35

Chemical Information

Glecaprevir

Glecaprevir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS3/4A protease inhibitor that targets the the viral RNA replication. In combination with [DB13878], glecaprevir is a useful therapy for patients who experienced therapeutic failure from other NS3/4A protease inhibitors. It demonstrates a high genetic barrier against resistance mutations of the virus. In cell cultures, the emergence of amino acid substitutions at NS3 resistance-associated positions A156 or D/Q168 in HCV genotype 1a, 2a or 3a replicons led to reduced susceptibility to glecaprevir. The combinations of amino acid substitutions at NS3 position Y65H and D/Q168 also results in greater reductions in glecaprevir susceptibility, and NS3 Q80R in genotype 3a patients also leads to glecaprevir resistance. Glecaprevir is available as an oral combination therapy with [DB13878] under the brand name Mavyret. This fixed-dose combination therapy was FDA-approved in August 2017 to treat adults with chronic hepatitis C virus (HCV) genotypes 1-6 without cirrhosis (liver disease) or with mild cirrhosis, including patients with moderate to severe kidney disease and those who are on dialysis. Mavyret is also indicated for HCV genotype 1-infected patients who have been previously treated with regimens either containing an NS5A inhibitor or an NS3/4A protease inhibitor, but not both. Hepatitis C viral infection often leads to decreased liver function and subsequent liver failure, causing a significantly negative impact on the patients' quality of life. The ultimate goal of the combination treatment is to achieve sustained virologic response (SVR) and cure the patients from the infection. In clinical trials, this combination therapy achieved SVR12 rate, or undetectable Hepatitis C for twelve or more weeks after the end of treatment, of ≥93% across genotypes 1a, 2a, 3a, 4, 5 and 6. As of June 2025, the FDA approved an expanded indication for Mavyret, making it the first and only direct-acting antiviral therapy approved for the treatment of both acute and chronic HCV in patients aged three years and older.

CAS Number1365970-03-1
PubChem CID66828839
IUPAC Name(1R,14E,18R,22R,26S,29S)-26-tert-butyl-N-[(1R,2R)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-13,13-difluoro-24,27-dioxo-2,17,23-trioxa-4,11,25,28-tetrazapentacyclo[26.2.1.03,12.05,10.018,22]hentriaconta-3,5,7,9,11,14-hexaene-29-carboxamide
Molecular FormulaC38H46F4N6O9S
Molecular Weight838.9
XLogP4.6
Topological Polar Surface Area204
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count15
Rotatable Bond Count7
Heavy Atom Count58
Formal Charge0
Complexity1760
SMILES
CC1(CC1)S(=O)(=O)NC(=O)[C@]2(C[C@H]2C(F)F)NC(=O)[C@@H]3C[C@@H]4CN3C(=O)[C@@H](NC(=O)O[C@@H]5CCC[C@H]5OC/C=C/C(C6=NC7=CC=CC=C7N=C6O4)(F)F)C(C)(C)C
InChI
InChI=1S/C38H46F4N6O9S/c1-35(2,3)28-32(50)48-19-20(17-24(48)30(49)46-37(18-21(37)29(39)40)33(51)47-58(53,54)36(4)14-15-36)56-31-27(43-22-9-5-6-10-23(22)44-31)38(41,42)13-8-16-55-25-11-7-12-26(25)57-34(52)45-28/h5-6,8-10,13,20-21,24-26,28-29H,7,11-12,14-19H2,1-4H3,(H,45,52)(H,46,49)(H,47,51)/b13-8+/t20-,21+,24+,25-,26-,28-,37-/m1/s1
InChIKey
MLSQGNCUYAMAHD-ITNVBOSISA-N
Chemical Structure
2D Structure
2D structure of Glecaprevir
CAS: 1365970-03-1
CID: 66828839
Formula: C38H46F4N6O9S
MW: 838.9
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight838.9
XLogP34.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count15
Rotatable Bond Count7
Exact Mass838.29831089
Monoisotopic Mass838.29831089
Topological Polar Surface Area204 Ų
Heavy Atom Count58
Formal Charge0
Complexity1760
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes