Pibrentasvir
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MedKoo CAT#: 528903

CAS#: 1353900-92-1 (free)

Description: Pibrentasvir, also known as ABT-530, is a protease inhibitor potentially for the treatment of HCV infection.

Chemical Structure

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Pibrentasvir
CAS# 1353900-92-1 (free)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 528903
Name: Pibrentasvir
CAS#: 1353900-92-1 (free)
Chemical Formula: C57H65F5N10O8
Exact Mass: 1,112.49
Molecular Weight: 1,113.200
Elemental Analysis: C, 61.50; H, 5.89; F, 8.53; N, 12.58; O, 11.50

Price and Availability

Size Price Availability Quantity
25mg USD 120 Ready to ship
50mg USD 200 Ready to ship
100mg USD 320 Ready to ship
200mg USD 550 Ready to ship
500mg USD 1250 Ready to ship
1g USD 2250 Ready to ship
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Related CAS #: 1821461-48-6 (butanamine hydrate)   1353900-92-1 (free)    

Synonym: ABT-530; ABT530; ABT 530, A-1325912; A 1325912; A1325912; A-1325912.0; A 1325912.0; A1325912.0; Pibrentasvir.

IUPAC/Chemical Name: dimethyl ((2S,2'S,3R,3'R)-((2S,2'S)-(((2R,5R)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis(6-fluoro-1H-benzo[d]imidazole-5,2-diyl))bis(pyrrolidine-2,1-diyl))bis(3-methoxy-1-oxobutane-1,2-diyl))dicarbamate

InChi Key: VJYSBPDEJWLKKJ-NLIMODCCSA-N

InChi Code: InChI=1S/C57H65F5N10O8/c1-29(77-3)49(67-56(75)79-5)54(73)70-19-7-9-47(70)52-63-41-25-35(37(59)27-43(41)65-52)45-15-16-46(72(45)34-23-39(61)51(40(62)24-34)69-21-17-32(18-22-69)31-11-13-33(58)14-12-31)36-26-42-44(28-38(36)60)66-53(64-42)48-10-8-20-71(48)55(74)50(30(2)78-4)68-57(76)80-6/h11-14,23-30,32,45-50H,7-10,15-22H2,1-6H3,(H,63,65)(H,64,66)(H,67,75)(H,68,76)/t29-,30-,45-,46-,47+,48+,49+,50+/m1/s1

SMILES Code: FC1=CC=C(C=C1)C2CCN(CC2)C3=C(C=C(C=C3F)N4[C@H](CC[C@@H]4C5=C(F)C=C6NC([C@@H]7CCCN7C([C@@H](NC(OC)=O)[C@H](OC)C)=O)=NC6=C5)C8=C(C=C9C(N=C([C@@H]%10CCCN%10C([C@@H](NC(OC)=O)[C@H](OC)C)=O)N9)=C8)F)F

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: Pibrentasvir (ABT-530) is a hepatitis C virus (HCV) NS5A inhibitor with EC50 ranging from 1.4 pM to 5.0 pM.
In vitro activity: Pibrentasvir is a next-generation NS5A inhibitor with potent (EC50s, 1.4 to 5.0 pM) and pan-genotypic antiviral activity against HCV replicons containing NS5A from all major HCV genotypes. Pibrentasvir demonstrated similar in vitro antiviral activities against replicons with NS5A from a panel of clinical samples of genotypes 1 to 6, indicating that pibrentasvir can inhibit HCV with clinically relevant sequence diversity in NS5A. In addition, pibrentasvir retained its activity against common NS5A amino acid substitutions that confer resistance to other NS5A inhibitors. It also demonstrated a high genetic barrier to resistance, selecting a small number or no colonies with resistance-conferring amino acid substitutions in replicons containing NS5A from genotypes 1a, 1b, 2a, 2b, 3a, 4a, 5a, and 6a. Pibrentasvir was active against key resistance-associated amino acid substitutions for NS3/4A PIs or NS5B polymerase inhibitors. The combination of pibrentasvir with HCV inhibitors of other classes produced synergistic antiviral activity in vitro. Reference: Antimicrob Agents Chemother. 2017 Apr 24;61(5):e02558-16. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5404558/
In vivo activity: A research program to discover solubilizing prodrugs of the HCV NS5A inhibitor pibrentasvir (PIB) identified phosphomethyl analog 2 and trimethyl-lock (TML) prodrug 9. The prodrug moiety is attached to a benzimidazole nitrogen atom via an oxymethyl linkage to allow for rapid and complete release of the drug for absorption following phosphate removal by intestinal alkaline phosphatase. These prodrugs have good hydrolytic stability properties and improved solubility compared to PIB, both in aqueous buffer (pH 7) and FESSIF (pH 5). TML prodrug 9 provided superior in vivo performance, delivering high plasma concentrations of PIB in PK studies conducted in mice, dogs, and monkeys. The improved dissolution properties of these phosphate prodrugs provide them the potential to simplify drug dosage forms for PIB-containing HCV therapy. Reference: J Med Chem. 2020 Oct 8;63(19):11034-11044. https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c00956

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 18.00
Ethanol 10.0 9.00

Preparing Stock Solutions

The following data is based on the product molecular weight 1,113.20 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. Ng TI, Krishnan P, Pilot-Matias T, Kati W, Schnell G, Beyer J, Reisch T, Lu L, Dekhtyar T, Irvin M, Tripathi R, Maring C, Randolph JT, Wagner R, Collins C. In Vitro Antiviral Activity and Resistance Profile of the Next-Generation Hepatitis C Virus NS5A Inhibitor Pibrentasvir. Antimicrob Agents Chemother. 2017 Apr 24;61(5):e02558-16. doi: 10.1128/AAC.02558-16. PMID: 28193664; PMCID: PMC5404558. 2. Randolph JT, Voight EA, Greszler SN, Uno BE, Newton JN, Gleason KM, Stolarik D, Van Handel C, Bow DAJ, DeGoey DA. Prodrug Strategies to Improve the Solubility of the HCV NS5A Inhibitor Pibrentasvir (ABT-530). J Med Chem. 2020 Oct 8;63(19):11034-11044. doi: 10.1021/acs.jmedchem.0c00956. Epub 2020 Sep 17. PMID: 32881503.
In vitro protocol: 1. Ng TI, Krishnan P, Pilot-Matias T, Kati W, Schnell G, Beyer J, Reisch T, Lu L, Dekhtyar T, Irvin M, Tripathi R, Maring C, Randolph JT, Wagner R, Collins C. In Vitro Antiviral Activity and Resistance Profile of the Next-Generation Hepatitis C Virus NS5A Inhibitor Pibrentasvir. Antimicrob Agents Chemother. 2017 Apr 24;61(5):e02558-16. doi: 10.1128/AAC.02558-16. PMID: 28193664; PMCID: PMC5404558.
In vivo protocol: 1. Randolph JT, Voight EA, Greszler SN, Uno BE, Newton JN, Gleason KM, Stolarik D, Van Handel C, Bow DAJ, DeGoey DA. Prodrug Strategies to Improve the Solubility of the HCV NS5A Inhibitor Pibrentasvir (ABT-530). J Med Chem. 2020 Oct 8;63(19):11034-11044. doi: 10.1021/acs.jmedchem.0c00956. Epub 2020 Sep 17. PMID: 32881503.

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1: Mensa FJ, Lovell S, Pilot-Matias T, Liu W. Glecaprevir/pibrentasvir for the treatment of chronic hepatitis C virus infection. Future Microbiol. 2019 Jan;14:89-110. doi: 10.2217/fmb-2018-0233. Epub 2018 Nov 30. Review. PubMed PMID: 30499343.

2: Clinical Review Report: Glecaprevir / Pibrentasvir (Maviret): (AbbVie Corporation): Indication: Hepatitis C genotype 1 to 6 [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Feb. Available from http://www.ncbi.nlm.nih.gov/books/NBK533768/ PubMed PMID: 30462453.

3: Pharmacoeconomic Review Report: Glecaprevir / Pibrentasvir (Maviret): (AbbVie Corporation): Indication: Hepatitis C genotype 1 to 6 [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Feb. Available from http://www.ncbi.nlm.nih.gov/books/NBK533682/ PubMed PMID: 30462452.

4: CADTH Canadian Drug Expert Committee Recommendation: Glecaprevir / Pibrentasvir (Maviret — Abbvie Corporation): Indication: Chronic hepatitis C virus infection [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Jan. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK533338/ PubMed PMID: 30457786.

5: Glecaprevir/pibrentasvir for hepatitis C. Aust Prescr. 2018 Oct;41(5):169-170. doi: 10.18773/austprescr.2018.050. Epub 2018 Aug 2. Review. PubMed PMID: 30410216; PubMed Central PMCID: PMC6202291.

6: Pearlman BL, Hinds AE. Review article: novel antivirals for hepatitis C-sofosbuvir/velpatasvir/voxilaprevir, glecaprevir/pibrentasvir. Aliment Pharmacol Ther. 2018 Nov;48(9):914-923. doi: 10.1111/apt.14977. Epub 2018 Oct 4. Review. PubMed PMID: 30288771.

7: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK525500/ PubMed PMID: 30222292.

8: Nehra V, Rizza SA, Temesgen Z. Glecaprevir/pibrentasvir for the treatment of chronic hepatitis C virus infection in adults. Drugs Today (Barc). 2018 Jul;54(7):407-421. doi: 10.1358/dot.2018.54.7.2828188. Review. PubMed PMID: 30090878.

9: Abutaleb A, Kottilil S, Wilson E. Glecaprevir/pibrentasvir expands reach while reducing cost and duration of hepatitis C virus therapy. Hepatol Int. 2018 May;12(3):214-222. doi: 10.1007/s12072-018-9873-y. Epub 2018 May 29. Review. PubMed PMID: 29845496; PubMed Central PMCID: PMC6436099.

10: Carrion AF, Martin P. Glecaprevir + pibrentasvir for treatment of hepatitis C. Expert Opin Pharmacother. 2018 Mar;19(4):413-419. doi: 10.1080/14656566.2018.1444030. Epub 2018 Mar 7. Review. PubMed PMID: 29465262.

11: Hubbard H, Lawitz E. Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C. Expert Rev Gastroenterol Hepatol. 2018 Jan;12(1):9-17. doi: 10.1080/17474124.2018.1411802. Epub 2017 Dec 5. Review. PubMed PMID: 29187007.

12: Lamb YN. Glecaprevir/Pibrentasvir: First Global Approval. Drugs. 2017 Oct;77(16):1797-1804. doi: 10.1007/s40265-017-0817-y. Review. PubMed PMID: 28929412.

1. Ohya K, Imamura M, Teraoka Y, Uchida T, Fujino H, Nakahara T, Ono A, Murakami E, Yamauchi M, Kawaoka T, Miki D, Tsuge M, Abe-Chayama H, Hayes CN, Aikata H, Ishida Y, Tateno C, Song H, Miyayama Y, Hijikata M, Chayama K. Novel drug resistance-associated substitutions against pibrentasvir emerged in genotype 1b hepatitis C virus-infected human hepatocyte transplanted mice. Biochem Biophys Res Commun. 2021 Apr 28;559:78-83. doi: 10.1016/j.bbrc.2021.04.062. Epub ahead of print. PMID: 33932902.