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MedKoo Cat#: 330335 | Name: Bictegravir sodium

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 sodium
Bictegravir sodium
CAS#1807988-02-8 (sodium)

Theoretical Analysis

MedKoo Cat#: 330335

Name: Bictegravir sodium

CAS#: 1807988-02-8 (sodium)

Chemical Formula: C21H17F3N3NaO5

Exact Mass: 0.0000

Molecular Weight: 471.37

Elemental Analysis: C, 53.51; H, 3.64; F, 12.09; N, 8.91; Na, 4.88; O, 16.97

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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; Bictegravir sodium
IUPAC/Chemical Name
sodium (2R,5S,13aR)-7,9-dioxo-10-((2,4,6-trifluorobenzyl)carbamoyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepin-8-olate
InChi Key
WJNFBIVCQMPPJC-FQYDJHLKSA-M
InChi Code
InChI=1S/C21H18F3N3O5.Na/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);/q;+1/p-1/t10-,11+,16+;/m0./s1
SMILES Code
[O-]C(C(C(C(NCC1=C(F)C=C(F)C=C1F)=O)=C2)=O)=C3N2C[C@@]4([H])O[C@](C5)([H])CC[C@]5([H])N4C3=O.[Na+]
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 471.37 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
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.

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