Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C38H46F4N6O9S |
| Molecular Weight | 838.865 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@H](N(C1)C(=O)[C@@H](NC(=O)O[C@]3([H])CCC[C@@]3([H])OC\C=C\C(F)(F)C4=NC5=CC=CC=C5N=C4O2)C(C)(C)C)C(=O)N[C@@]6(C[C@H]6C(F)F)C(=O)NS(=O)(=O)C7(C)CC7
InChI
InChIKey=MLSQGNCUYAMAHD-ITNVBOSISA-N
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
| Molecular Formula | C38H46F4N6O9S |
| Molecular Weight | 838.865 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 Pibrentasvir, 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. Glecaprevir is available as an oral combination therapy with Pibrentasvir under the brand name Mavyret. On 3 August 2017 the FDA approved the combination for hepatitis C treatment. Mavyret is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV)
genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh
A). Mavyret is also indicated for the treatment of adult patients with HCV genotype 1
infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor
or an NS3/4A protease inhibitor (PI), but not both.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095231 |
3.5 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MAVYRET Approved UseMAVYRET is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV)
genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh
A). MAVYRET is also indicated for the treatment of adult patients with HCV genotype 1
infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor
or an NS3/4A protease inhibitor (PI), but not both. Launch Date2017 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1270 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28800195 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: PIBRENTASVIR |
GLECAPREVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4500 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28800195 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: PIBRENTASVIR |
GLECAPREVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.69 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28800195 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: PIBRENTASVIR |
GLECAPREVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
700 mg 1 times / day multiple, oral Highest studied dose Dose: 700 mg, 1 times / day Route: oral Route: multiple Dose: 700 mg, 1 times / day Sources: |
unhealthy, 50.3 ± 9.04 years n = 9 Health Status: unhealthy Condition: chronic HCV infection Age Group: 50.3 ± 9.04 years Sex: M Population Size: 9 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Retreatment of patients with treatment failure of direct-acting antivirals: Focus on hepatitis C virus genotype 1b. | 2017 Dec 14 |
|
| Formulary Drug Review: Etelcalcetide. | 2017 Nov |
|
| Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C. | 2018 Jan |
|
| Glecaprevir-Pibrentasvir for 8 or 12 Weeks in HCV Genotype 1 or 3 Infection. | 2018 Jan 25 |
|
| Effects of Renal Impairment and Hemodialysis on the Pharmacokinetics and Safety of the Glecaprevir and Pibrentasvir Combination in Hepatitis C Virus-Negative Subjects. | 2018 Mar |
Sample Use Guides
Each tablet of Mavyret (glecaprevir and pibrentasvir): 100 mg glecaprevir and 40 mg pibrentasvir. Recommended dosage: Three tablets (total daily dose: glecaprevir 300 mg
and pibrentasvir 120 mg) taken orally once daily with food.
Route of Administration:
Oral
Glecaprevir inhibited the enzymatic activity of purified NS3/4A proteases from HCV genotypes 1 to 6 in vitro (half-maximal [50%] inhibitory concentration = 3.5 to 11.3 nM) and the replication of stable HCV subgenomic replicons containing proteases from genotypes 1 to 6 (50% effective concentration [EC50] = 0.21 to 4.6 nM). Glecaprevir had a median EC50 of 0.30 nM (range, 0.05 to 3.8 nM) for HCV replicons containing proteases from 40 samples from patients infected with HCV genotypes 1 to 5.
| Substance Class |
Chemical
Created
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| Record UNII |
K6BUU8J72P
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Validated (UNII)
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FDA ORPHAN DRUG |
550516
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WHO-ATC |
J05AP57
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N0000182639
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CHEMBL3545363
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m12026
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Glecaprevir
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Glecaprevir
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TRANSPORTER -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TRANSPORTER -> SUBSTRATE |
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BINDER->LIGAND |
GLE is approximately 97.5% bound to human plasma proteins independent of concentration from 0.1 to 30 μM (800 to 25,200 ng/mL).
BINDING
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TARGET -> INHIBITOR |
ABT-493 demonstrates comparable acti vity against HCV replicons containing NS3 genes from genotype 1a, 1b, 2a, 3a, 4a, and 6a
EC50
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TRANSPORTER -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
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SOLVATE->ANHYDROUS |
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TRANSPORTER -> INHIBITOR |
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TRANSPORTER -> INHIBITOR |
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TRANSPORTER -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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| blood-to-plasma ratio | PHARMACOKINETIC |
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| Tmax | PHARMACOKINETIC |
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