WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 314270
CAS#: 379270-37-8 (free base)
Description: Tenofovir alafenamide, also known as TAF and GS-7340, is a nucleotide reverse transcriptase inhibitor (NRTIs) and a novel prodrug of tenofovir. By blocking reverse transcriptase, TAF prevent HIV from multiplying and can reduce the amount of HIV in the body. Tenofovir alafenamide is a prodrug, which means that it is an inactive drug. In the body, tenofovir alafenamide is converted to tenofovir diphosphate (TFV-DP). Tenofovir alafenamide fumarate was approved in November 2015 for treatment of HIV-1.
MedKoo Cat#: 314270
Name: Tenofovir alafenamide (free base)
CAS#: 379270-37-8 (free base)
Chemical Formula: C21H29N6O5P
Exact Mass: 476.1937
Molecular Weight: 476.47
Elemental Analysis: C, 52.94; H, 6.13; N, 17.64; O, 16.79; P, 6.50
Related CAS #: 379270-38-9 (fumarate) 1392275-56-7 (hemifumarate) 379270-37-8 (free base)
Synonym: GS7340; GS-7340; GS 7340; TAF; Tenofovir alafenamide; Genvoya.
IUPAC/Chemical Name: (S)-isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate
InChi Key: LDEKQSIMHVQZJK-AZFZMOAFSA-N
InChi Code: InChI=1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33?/m1/s1
SMILES Code: C[C@H](N[P@@](OC1=CC=CC=C1)(CO[C@H](C)CN2C=NC3=C(N)N=CN=C23)=O)C(OC(C)C)=O
Appearance: White to off-white 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
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 73.0 | 153.21 | |
| Water | 3.34 | 7.01 | |
| Ethanol | 55.0 | 115.43 | |
| DMF | 25.0 | 52.47 | |
| PBS (pH 7.2) | 2.0 | 4.2 |
The following data is based on the product molecular weight 476.47 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 |
1: Shafran SD, Di Perri G, Esser S, Lelièvre JD, Parczewski M. Planning HIV therapy to prevent future comorbidities: patient years for tenofovir alafenamide. HIV Med. 2019 Jun;20 Suppl 7:1-16. doi: 10.1111/hiv.12755. Review. PubMed PMID: 31099116.
2: 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.
3: Common Drug Review New Combination Product Submission: Darunavir/Cobicistat/Emtricitabine/Tenofovir alafenamide (Symtuza): (Janssen Canada Inc.): Indication: A complete regimen for the treatment of HIV type 1 infection in adults and adolescents (aged 12 years and older with body weight at least 40 kg) with no known mutations associated with resistance to the individual components of Symtuza [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK540525/ PubMed PMID: 31034191.
4: CADTH Canadian Drug Expert Committee Recommendation: Darunavir/Cobicistat/Emtricitabine/Tenofovir Alafenamide (Symtuza — Janssen Inc.): Indication: Treatment of HIV type 1 (HIV-1) infection [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Jul. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK540287/ PubMed PMID: 31013021.
5: 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.
6: 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.
7: 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.
8: Pharmacoeconomic Review Report: Emtricitabine/tenofovir alafenamide (Descovy) [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK539225/ PubMed PMID: 30933443.
9: Clinical Review Report: Emtricitabine/tenofovir alafenamide fumarate (Descovy) [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK538758/ PubMed PMID: 30883070.
10: CADTH Canadian Drug Expert Committee Final Recommendation: Emtricitabine/Tenofovir Alafenamide: (Descovy — Gilead Sciences Canada, Inc.): Indication: HIV-1 Infection [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Aug. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK538372/ PubMed PMID: 30860687.
11: 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.
12: Giacomet V, Cossu MV, Capetti AF, Zuccotti G, Rizzardini G. An evaluation of elvitegravir plus cobicistat plus tenofovir alafenamide plus emtricitabine as a single-tablet regimen for the treatment of HIV in children and adolescents. Expert Opin Pharmacother. 2019 Feb;20(3):269-276. doi: 10.1080/14656566.2018.1559299. Epub 2018 Dec 26. Review. PubMed PMID: 30586314.
13: Clinical Review Report: Tenofovir Alafenamide (Vemlidy): (Gilead Sciences Canada, Inc.): Indication: Treatment of chronic hepatitis B in adults with compensated liver disease [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Apr. Available from http://www.ncbi.nlm.nih.gov/books/NBK533926/ PubMed PMID: 30475544.
14: 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.
15: Squillace N, Bozzi G, Colella E, Gori A, Bandera A. Darunavir-cobicistat-emtricitabine-tenofovir alafenamide: safety and efficacy of a protease inhibitor in the modern era. Drug Des Devel Ther. 2018 Oct 29;12:3635-3643. doi: 10.2147/DDDT.S147493. eCollection 2018. Review. PubMed PMID: 30464395; PubMed Central PMCID: PMC6211373.
16: 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.
17: Pharmacoeconomic Review Report: Tenofovir Alafenamide (Vemlidy): (Gilead Sciences Canada, Inc.): Indication: Treatment of chronic hepatitis B in adults with compensated liver disease [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Apr. Available from http://www.ncbi.nlm.nih.gov/books/NBK532825/ PubMed PMID: 30427623.
18: CADTH Canadian Drug Expert Committee Recommendation: Tenofovir Alafenamide (Vemlidy - Gilead Sciences Canada, Inc.): Indication: Chronic Hepatitis B [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Mar 28. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK532703/ PubMed PMID: 30403460.
19: Childs-Kean LM, Egelund EF, Jourjy J. Tenofovir Alafenamide for the Treatment of Chronic Hepatitis B Monoinfection. Pharmacotherapy. 2018 Oct;38(10):1051-1057. doi: 10.1002/phar.2174. Epub 2018 Sep 9. Review. PubMed PMID: 30120841.
20: Byrne R, Carey I, Agarwal K. Tenofovir alafenamide in the treatment of chronic hepatitis B virus infection: rationale and clinical trial evidence. Therap Adv Gastroenterol. 2018 Jul 16;11:1756284818786108. doi: 10.1177/1756284818786108. eCollection 2018. Review. PubMed PMID: 30034532; PubMed Central PMCID: PMC6048601.
Related CAS#
CAS#379270-38-9 =Tenofovir alafenamide fumarate, 1:1
CAS#1392275-56-7= Tenofovir alafenamide hemifumarate, 2:1
CAS#379270-37-8 = Tenofovir alafenamide
