Tenofovir disoproxil

Tenofovir
Clinical data
Other names	9-(2-Phosphonyl-methoxypropyly)adenine (PMPA)
MedlinePlus	a602018
ATC code	None;
Legal status
Legal status	US: WARNING;
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	EU EMA: by INN; US DailyMed: Tenofovir_disoproxil;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth (tablets)
ATC code	J05AF07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-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 trade name Viread among others, is a medication used to treat chronic hepatitis B and to prevent and treat HIV/AIDS. It is generally recommended for use with other antiretrovirals. 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. It is sold both by itself and together in combinations such as emtricitabine/tenofovir, efavirenz/emtricitabine/tenofovir, and elvitegravir/cobicistat/emtricitabine/tenofovir. It does not cure HIV/AIDS or hepatitis B. It is available by mouth as a tablet or powder.

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

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

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