Tenofovir disoproxil

Tenofovir
Clinical data
Other names	9-(2-Phosphonyl-methoxypropyly)adenine (PMPA)
MedlinePlus	a602018
ATC code	None;
Pharmacokinetic data
Protein binding	< 1%
Metabolism	Phosphorylation
Metabolites	Tenofovir diphosphate (active metabolite)
Elimination half-life	17 hours
Excretion	Kidney
Identifiers
	IUPAC name ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid;
CAS Number	147127-20-6 ;
PubChem CID	464205;
DrugBank	DB14126 ;
ChemSpider	408154 ;
UNII	99YXE507IL;
KEGG	D06074 ;
ChEBI	CHEBI:63625;
ChEMBL	ChEMBL483 ;
CompTox Dashboard (EPA)	DTXSID9040132 ;
ECHA InfoCard	100.129.993
Chemical and physical data
Formula	C9H14N5O4P
Molar mass	287.216 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=P(O)(O)CO[C@H](C)Cn1c2ncnc(c2nc1)N;
	InChI 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 ; Key:SGOIRFVFHAKUTI-ZCFIWIBFSA-N ;
	(verify)

Tenofovir disoproxil
Clinical data
Pronunciation	/ˌtəˈnoʊfəvɪər ˌdɪsəˈprɑːksəl/
Trade names	Viread, others
Other names	Bis(POC)PMPA
AHFS/Drugs.com	Monograph
MedlinePlus	a602018
License data	US DailyMed: Tenofovir disoproxil;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AF07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	25%
Metabolism	Ester hydrolysis
Metabolites	Tenofovir
Identifiers
	IUPAC name Bis{[(isopropoxycarbonyl)oxy]methyl} ({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosphonate;
CAS Number	201341-05-1;
PubChem CID	5481350;
DrugBank	DB00300;
ChemSpider	4587262;
UNII	F4YU4LON7I;
KEGG	C13480;
ChEBI	CHEBI:63717;
ChEMBL	ChEMBL1538;
NIAID ChemDB	080741;
CompTox Dashboard (EPA)	DTXSID9040132 ;
ECHA InfoCard	100.129.993
Chemical and physical data
Formula	C19H30N5O10P
Molar mass	519.448 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C;
	InChI 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 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.^[3] It is generally recommended for use with other antiretrovirals.^[3] 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.^[3] It is sold both by itself and together in combinations such as emtricitabine/tenofovir, efavirenz/emtricitabine/tenofovir,^[3] and elvitegravir/cobicistat/emtricitabine/tenofovir.^[4] It does not cure HIV/AIDS or hepatitis B.^[3]^[5] It is available by mouth as a tablet or powder.^[3]

Common side effects include nausea, rash, diarrhea, headache, pain, depression, and weakness.^[3] Severe side effects include high blood lactate and an enlarged liver.^[3] There are no absolute contraindications.^[3] It is often recommended during pregnancy and appears to be safe.^[3] It is a nucleotide reverse transcriptase inhibitor and works by decreasing the ability of the viruses to replicate.^[3]

Tenofovir was patented in 1996 and approved for use in the United States in 2001.^[6] It is on the World Health Organization's List of Essential Medicines.^[7] It is available in the United States as a generic medication as of 2017.^[8]

^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Viread EPAR". European Medicines Agency (EMA). 5 February 2002. Retrieved 25 May 2024.
^ ^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.
^ "Stribild". PubChem. U.S. National Library of Medicine. Retrieved 6 February 2022.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.
^ 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.
^ "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.

[1] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[2] "Viread EPAR". European Medicines Agency (EMA). 5 February 2002. Retrieved 25 May 2024.

[AHFS2016-3] ^ ^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.

[4] "Stribild". PubChem. U.S. National Library of Medicine. Retrieved 6 February 2022.

[5] 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.

[6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.

[WHO21st-7] 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.

[8] "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.

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