Bictegravir | CAS#1611493-60-7 | HIV-1 Inhibitor

MedKoo Cat#: 326842 | Name: Bictegravir

Description:

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

Bictegravir, also known as GS-9883, is a potent, unboosted, once-Daily HIV-1 Integrase Strand Transfer Inhibitor (INSTI) (IC50 - 1.6 nM) with improved pharmacokinetics and in vitro resistance profile. Bictegravir, as part of a fixed-dose combination product containing bictegravir/emtricitabine/tenofovir alafenamide (BIC/FTC/TAF), is in Phase III development.

Chemical Structure

Bictegravir

CAS#1611493-60-7 (free acid)

Theoretical Analysis

MedKoo Cat#: 326842

Name: Bictegravir

CAS#: 1611493-60-7 (free acid)

Chemical Formula: C21H18F3N3O5

Exact Mass: 449.1199

Molecular Weight: 449.39

Elemental Analysis: C, 56.13; H, 4.04; F, 12.68; N, 9.35; O, 17.80

Price and Availability

Size	Price	Availability
50mg	USD 150.00	Ready to ship
1g	USD 350.00	Ready to Ship
2g	USD 550.00	Ready to ship
5g	USD 950.00	2 Weeks
10g	USD 1,650.00	2 Weeks

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Related CAS #

1611493-60-7 (free acid) 1807988-02-8 (sodium)

Synonym

GS-9883; GS 9883; GS9883; GS-9883-01; GS9883-01; GS 9883-01; Bictegravir

IUPAC/Chemical Name

(2R,5S,13aR)-8-hydroxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide

InChi Key

SOLUWJRYJLAZCX-LYOVBCGYSA-N

InChi Code

InChI=1S/C21H18F3N3O5/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1

SMILES Code

O=C(C1=CN(C2=C(O)C1=O)C[C@@]3([H])O[C@](C4)([H])CC[C@]4([H])N3C2=O)NCC5=C(F)C=C(F)C=C5F

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C8R08B09

QC Data

View QC data: current batch, Lot#C8R08B09

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Bictegravir (GS-9883) is a potent inhibitor of HIV-1 integrase with an IC50 of 7.5 nM.

In vitro activity:

Bictegravir (BIC; GS-9883), a novel, potent, once-daily, unboosted inhibitor of HIV-1 integrase (IN), specifically targets IN strand transfer activity (50% inhibitory concentration [IC50] of 7.5 ± 0.3 nM) and HIV-1 integration in cells. BIC exhibits potent and selective in vitro antiretroviral activity in both T-cell lines and primary human T lymphocytes, with 50% effective concentrations ranging from 1.5 to 2.4 nM and selectivity indices up to 8,700 relative to cytotoxicity. A high barrier to in vitro resistance emergence for BIC was also observed in viral breakthrough studies in the presence of constant clinically relevant drug concentrations. Reference: Antimicrob Agents Chemother. 2016 Nov 21;60(12):7086-7097. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5118987/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	86.7	192.48

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 449.39 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.

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. Tsiang M, Jones GS, Goldsmith J, Mulato A, Hansen D, Kan E, Tsai L, Bam RA, Stepan G, Stray KM, Niedziela-Majka A, Yant SR, Yu H, Kukolj G, Cihlar T, Lazerwith SE, White KL, Jin H. Antiviral Activity of Bictegravir (GS-9883), a Novel Potent HIV-1 Integrase Strand Transfer Inhibitor with an Improved Resistance Profile. Antimicrob Agents Chemother. 2016 Nov 21;60(12):7086-7097. doi: 10.1128/AAC.01474-16. PMID: 27645238; PMCID: PMC5118987.

In vitro protocol:

In vivo protocol:

TBD

1: Tiraboschi J, Imaz A, Khoo S, Niubo J, Prieto P, Saumoy M, Penchala SD, Garcia B, Padilla C, Videla S, Podzamczer D. Total and Unbound Bictegravir Concentrations and Viral Suppression in CSF of HIV-infected Patients (Spanish HIV/AIDS Research Network, PreEC/RIS 56). J Infect Dis. 2019 Nov 30. pii: jiz624. doi: 10.1093/infdis/jiz624. [Epub ahead of print] PubMed PMID: 31784745. 2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK547914/ PubMed PMID: 31643250. 3: Kityo C, Hagins D, Koenig E, Avihingsanon A, Chetchotisakd P, Supparatpinyo K, Gankina N, Pokrovsky V, Voronin E, Stephens JL, DeJesus E, Wang H, Acosta RK, Cao H, Quirk E, Martin H, Makadzange T. Switching to Fixed-Dose Bictegravir, Emtricitabine, and Tenofovir Alafenamide (B/F/TAF) in Virologically Suppressed HIV-1 Infected Women: A Randomized, Open-Label, Multicenter, Active-Controlled, Phase 3, Noninferiority Trial. J Acquir Immune Defic Syndr. 2019 Nov 1;82(3):321-328. doi: 10.1097/QAI.0000000000002137. PubMed PMID: 31609930. 4: Andreatta K, Willkom M, Martin R, Chang S, Wei L, Liu H, Liu YP, Graham H, Quirk E, Martin H, White KL. Erratum to: Switching to bictegravir/emtricitabine/tenofovir alafenamide maintained HIV-1 RNA suppression in participants with archived antiretroviral resistance including M184V/I. J Antimicrob Chemother. 2019 Dec 1;74(12):3646-3647. doi: 10.1093/jac/dkz412. PubMed PMID: 31562501; PubMed Central PMCID: PMC6857191. 5: Andreatta K, Willkom M, Martin R, Chang S, Wei L, Liu H, Liu YP, Graham H, Quirk E, Martin H, White KL. Switching to bictegravir/emtricitabine/tenofovir alafenamide maintained HIV-1 RNA suppression in participants with archived antiretroviral resistance including M184V/I. J Antimicrob Chemother. 2019 Dec 1;74(12):3555-3564. doi: 10.1093/jac/dkz347. PubMed PMID: 31430369; PubMed Central PMCID: PMC6857193. 6: Stellbrink HJ, Arribas JR, Stephens JL, Albrecht H, Sax PE, Maggiolo F, Creticos C, Martorell CT, Wei X, Acosta R, Collins SE, Brainard D, Martin H. Co-formulated bictegravir, emtricitabine, and tenofovir alafenamide versus dolutegravir with emtricitabine and tenofovir alafenamide for initial treatment of HIV-1 infection: week 96 results from a randomised, double-blind, multicentre, phase 3, non-inferiority trial. Lancet HIV. 2019 Jun;6(6):e364-e372. doi: 10.1016/S2352-3018(19)30080-3. Epub 2019 May 5. PubMed PMID: 31068272. 7: Barber TJ. Bictegravir and dolutegravir: head to head at 96 weeks. Lancet HIV. 2019 Jun;6(6):e342-e343. doi: 10.1016/S2352-3018(19)30135-3. Epub 2019 May 5. PubMed PMID: 31068271. 8: Wohl DA, Yazdanpanah Y, Baumgarten A, Clarke A, Thompson MA, Brinson C, Hagins D, Ramgopal MN, Antinori A, Wei X, Acosta R, Collins SE, Brainard D, Martin H. Bictegravir combined with emtricitabine and tenofovir alafenamide versus dolutegravir, abacavir, and lamivudine for initial treatment of HIV-1 infection: week 96 results from a randomised, double-blind, multicentre, phase 3, non-inferiority trial. Lancet HIV. 2019 Jun;6(6):e355-e363. doi: 10.1016/S2352-3018(19)30077-3. Epub 2019 May 5. PubMed PMID: 31068270. 9: Bictegravir/emtricitabine/tenofovir alafenamide for HIV infection. Aust Prescr. 2019 Apr;42(2):68-69. doi: 10.18773/austprescr.2019.016. Epub 2019 Feb 28. Review. PubMed PMID: 31048941; PubMed Central PMCID: PMC6478953. 10: Mandal S, Prathipati PK, Belshan M, Destache CJ. A potential long-acting bictegravir loaded nano-drug delivery system for HIV-1 infection: A proof-of-concept study. Antiviral Res. 2019 Jul;167:83-88. doi: 10.1016/j.antiviral.2019.04.007. Epub 2019 Apr 13. PubMed PMID: 30991088. 11: Clinical Review Report: Bictegravir/Emtricitabine/Tenofovir Alafenamide (B/FTC/TAF) (Biktarvy): (Gilead Sciences Canada, Inc.): Indication: A complete regimen for the treatment of HIV-1 infection in adults with no known substitution associated with resistance to the individual components of Biktarvy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Oct. Available from http://www.ncbi.nlm.nih.gov/books/NBK539526/ PubMed PMID: 30958669. 12: Pharmacoeconomic Review Report: Bictegravir/Emtricitabine/Tenofovir Alafenamide (B/FTC/TAF) (Biktarvy): (Gilead Sciences Canada, Inc.): Indication: A complete regimen for the treatment of HIV-1 infection in adults with no known substitution associated with resistance the individual components of Biktarvy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Oct. Available from http://www.ncbi.nlm.nih.gov/books/NBK539546/ PubMed PMID: 30958667. 13: CADTH Canadian Drug Expert Committee Recommendation: Bictegravir/Emtricitabine/Tenofovir Alafenamide (Biktarvy — Gilead Sciences Canada, Inc.): Indication: As a complete regimen for the treatment of human immunodeficiency virus-1 (HIV-1) infection in adults with no known substitution associated with resistance to the individual components of Biktarvy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Oct. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK539326/ PubMed PMID: 30942994. 14: Deeks ED. Correction to: Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2019 Apr;79(6):687. doi: 10.1007/s40265-019-01101-4. PubMed PMID: 30903610; PubMed Central PMCID: PMC6483951. 15: Smith RA, Raugi DN, Wu VH, Zavala CG, Song J, Diallo KM, Seydi M, Gottlieb GS; University of Washington-Dakar HIV-2 Study Group. Comparison of the Antiviral Activity of Bictegravir against HIV-1 and HIV-2 Isolates and Integrase Inhibitor-Resistant HIV-2 Mutants. Antimicrob Agents Chemother. 2019 Apr 25;63(5). pii: e00014-19. doi: 10.1128/AAC.00014-19. Print 2019 May. PubMed PMID: 30803972; PubMed Central PMCID: PMC6496081. 16: Acosta RK, Willkom M, Martin R, Chang S, Wei X, Garner W, Lutz J, Majeed S, SenGupta D, Martin H, Quirk E, White KL. Resistance Analysis of Bictegravir-Emtricitabine-Tenofovir Alafenamide in HIV-1 Treatment-Naive Patients through 48 Weeks. Antimicrob Agents Chemother. 2019 Apr 25;63(5). pii: e02533-18. doi: 10.1128/AAC.02533-18. Print 2019 May. PubMed PMID: 30803969; PubMed Central PMCID: PMC6496090. 17: Pham HT, Mesplède T. Bictegravir in a fixed-dose tablet with emtricitabine and tenofovir alafenamide for the treatment of HIV infection: pharmacology and clinical implications. Expert Opin Pharmacother. 2019 Mar;20(4):385-397. doi: 10.1080/14656566.2018.1560423. Epub 2019 Jan 30. Review. PubMed PMID: 30698467. 18: Hill L, Smith SR, Karris MY. Profile of bictegravir/emtricitabine/tenofovir alafenamide fixed dose combination and its potential in the treatment of HIV-1 infection: evidence to date. HIV AIDS (Auckl). 2018 Oct 29;10:203-213. doi: 10.2147/HIV.S145529. eCollection 2018. Review. PubMed PMID: 30464641; PubMed Central PMCID: PMC6214311. 19: Deeks ED. Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. Review. Erratum in: Drugs. 2019 Mar 22;:. PubMed PMID: 30460547; PubMed Central PMCID: PMC6424950. 20: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK525506/ PubMed PMID: 30222298.