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206184-49-8 , Tenofovir, CAS:206184-49-8

206184-49-8 , Tenofovir,
CAS:206184-49-8
C9H14N5O4P / 287.21
MFCD00943794

Tenofovir, 泰诺福韦

Tenofovir is a drug that belongs to the group of nucleoside analogues. It is used in the treatment of human immunodeficiency virus (HIV). Tenofovir is an antiviral prophylaxis and has been shown to reduce the risk of HIV infection among those who are at high risk for contracting the virus. Tenofovir disoproxil fumarate (TDF) is an acyclic nucleoside phosphonate, which inhibits HIV-1 reverse transcriptase. The oral prodrug tenofovir alafenamide hemifumarate (TAF) is a prodrug that can be activated by esterases in the gastrointestinal tract. TAF has low potency and does not require activation by esterases because it undergoes hydrolysis by hepatic carboxylesterase, leading to a higher bioavailability than TDF. 

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Tenofovir is a nucleotide analog reverse transcriptase inhibitor, and is widely used as an antiretroviral agent, for the treatment of HIV infection.

Tenofovir(GS 1278, PMPA) is an antiretroviral drug known as nucleotide analogue reverse transcriptase inhibitors (NRTIs), which block reverse transcriptase, a crucial virus enzyme in HIV-1 and HBV. IC50 Value:0.5-2.2 uM (HIV-1); 1.6-4.9 uM (HIV-2) Target: NRTIsin vitro: Tenofovir hydrate reduces the viral cytopathic effect of HIV-1(IIIB), HIV-2(ROD) and HIV(EHO) with EC50 of 1.15 μg/mL, 1.12 μg/mL and 1.05 μg/mL in MT-4 cells. Tenofovir hydrate also reduces the viral cytopathic effect of SIV(mac251), SIV(B670) ,SHIV(89.6) and SHIV(RTSHIV). Tenofovir hydrate inhibits hepatitis B virus (HBV) activity in HepG2 2.2. 5, HepAD38 and HepAD79 cells. Tenofovir hydrate (4 μM) completely inhibits the growth of HIVIIIB in MT-2 cells. Tenofovir hydrate inhibits synthesis of negative strand strong-stop DNA with IC50 of 9 M for wild-type RT, 6 M for M184V RT and 50 M for K65R RT. in vivo: Tenofovir hydrate (30 mg/kg) completely prevents SIV infection in all macaques without toxicity. Tenofovir hydrate treatment reduces plasma viral RNA levels to undetectable, with parallel decreases in the infectivity of plasma and infectious cells in peripheral blood mononuclear cells and cerebrospinal fluid (CSF) and stabilization of CD4+ T-cell numbers. Tenofovir hydrate (30 mg/kg, s.c.) completely abrogates HIV infection via intravaginal exposure in pig-tailed macaques. Clinical indications: HIV-1 infection; hepatitis B virusinfectionsFDA Approved Date: 12 July 2006Toxicity: The mean change of eGFR from the baseline to the six months of follow-up was +/-1.32 and +/- 5.88 mL/minute in the TDF and AZT groups. Proximal tubular dysfunction was not noted at three and six months of follow-up. However patients in the TDF group had lower serum phosphate and higher renal potassium loss than the AZT group at six months of follow-up (p = 0.08 and p = 0.09, respectively). No patients in the two groups with distal tubular dysfunctions were noted.

CAS Number

206184-49-8

Product Name

Tenofovir

IUPAC Name

[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid;hydrate

Molecular Formula

C9H16N5O5P

Molecular Weight

305.23 g/mol

InChI

InChI=1S/C9H14N5O4P.H2O/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);1H2/t6-;/m1./s1

InChI Key

PINIEAOMWQJGBW-FYZOBXCZSA-N

SMILES

CC(CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O.O

Synonyms

(R)-9-(2-phosphonylmethoxypropyl)adenine, 9-(2-phosphonomethoxypropyl)adenine, 9-(2-phosphonylmethoxypropyl)adenine, 9-(2-phosphonylmethoxypropyl)adenine, (+-)-isomer, 9-(2-Phosphonylmethoxypropyl)adenine, (R)-isomer - T357098, 9-(2-phosphonylmethoxypropyl)adenine, (S)-isomer, 9-PMPA (tenofovir), Disoproxil Fumarate, Tenofovir, Disoproxil, Tenofovir, Fumarate, Tenofovir Disoproxil, tenofovir, tenofovir disoproxil, tenofovir disoproxil fumarate, Viread

Canonical SMILES

CC(CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O.O

Isomeric SMILES

C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O.O


CAS No: 147127-20-6,206184-49-8 Synonyms: (R)-9-(2-Phosphonoylmethoxypropyl)adenine1-(6-aminopurin-9-yl)propan-2-yloxymethylphosphonic acid(R)-[[2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic acid MDL No: MFCD00943794 Chemical Formula: C9H14N5O4P Molecular Weight: 287.21


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