Tenofovir disoproxil

"Tenofovir" redirects here. For the newer tenofovir prodrug, see Tenofovir alafenamide.

Tenofovir disoproxil
Clinical data
Pronunciation/ˌtəˈnoʊfəvɪər ˌdɪsəˈprɑːksəl/
Trade namesViread, others
Other namesBis(POC)PMPA
AHFS/Drugs.comMonograph
MedlinePlusa602018
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability25%
MetabolismEster hydrolysis
MetabolitesTenofovir
Identifiers
  • Bis{[(isopropoxycarbonyl)oxy]methyl} ({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosphonate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.129.993 Edit this at Wikidata
Chemical and physical data
FormulaC19H30N5O10P
Molar mass519.448 g·mol−1
3D model (JSmol)
  • C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C
  • InChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1
  • Key:JFVZFKDSXNQEJW-CQSZACIVSA-N
Tenofovir
Clinical data
Other names9-(2-Phosphonyl-methoxypropyly)adenine (PMPA)
MedlinePlusa602018
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Protein binding< 1%
MetabolismPhosphorylation
MetabolitesTenofovir diphosphate (active metabolite)
Elimination half-life17 hours
ExcretionKidney
Identifiers
  • ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.129.993 Edit this at Wikidata
Chemical and physical data
FormulaC9H14N5O4P
Molar mass287.216 g·mol−1
3D model (JSmol)
  • O=P(O)(O)CO[C@H](C)Cn1c2ncnc(c2nc1)N
  • InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1 checkY
  • Key:SGOIRFVFHAKUTI-ZCFIWIBFSA-N checkY
  (verify)

Tenofovir disoproxil, sold under the brand name Viread among others, is a medication used to treat chronic hepatitis B and to prevent and treat HIV/AIDS.[4] It is generally recommended for use with other antiretrovirals.[4] It may be used for prevention of HIV/AIDS among those at high risk before exposure, and after a needlestick injury or other potential exposure.[4] It is sold both by itself and together in combinations such as emtricitabine/tenofovir, efavirenz/emtricitabine/tenofovir,[4] and elvitegravir/cobicistat/emtricitabine/tenofovir.[5] It does not cure HIV/AIDS or hepatitis B.[4][6] It is available by mouth as a tablet or powder.[4]

Common side effects include nausea, rash, diarrhea, headache, pain, depression, and weakness.[4] Severe side effects include high blood lactate and an enlarged liver.[4] There are no absolute contraindications.[4] It is often recommended during pregnancy and appears to be safe.[4] It is a nucleotide reverse transcriptase inhibitor and works by decreasing the ability of the viruses to replicate.[4]

Tenofovir was patented in 1996 and approved for use in the United States in 2001.[7] It is on the World Health Organization's List of Essential Medicines.[8] It is available in the United States as a generic medication as of 2017.[9]

  1. ^ a b "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ "Viread EPAR". European Medicines Agency (EMA). 5 February 2002. Retrieved 25 May 2024.
  4. ^ a b c d e f g h i j k "Tenofovir Disoproxil Fumarate". The American Society of Health-System Pharmacists. Archived from the original on 30 November 2016. Retrieved 29 November 2016.
  5. ^ "Stribild". PubChem. U.S. National Library of Medicine. Retrieved 6 February 2022.
  6. ^ Martin P, Lau DT, Nguyen MH, Janssen HL, Dieterich DT, Peters MG, et al. (November 2015). "A Treatment Algorithm for the Management of Chronic Hepatitis B Virus Infection in the United States: 2015 Update". Clinical Gastroenterology and Hepatology. 13 (12): 2071–87.e16. doi:10.1016/j.cgh.2015.07.007. PMID 26188135.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ "Teva Announces Exclusive Launch of a Generic version of Viread in the United States". www.tevapharm.com. Archived from the original on 6 November 2018. Retrieved 6 November 2018.