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202138-50-9 molecular structure
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(2E)-but-2-enedioic acid bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate

ChemBase ID: 72667
Molecular Formular: C23H34N5O14P
Molecular Mass: 635.514921
Monoisotopic Mass: 635.18398742
SMILES and InChIs

SMILES:
n1cnc2c(c1N)ncn2C[C@H](OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C.C(=C\C(=O)O)/C(=O)O
Canonical SMILES:
C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.OC(=O)/C=C/C(=O)O
InChI:
InChI=1S/C19H30N5O10P.C4H4O4/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;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1
InChIKey:
VCMJCVGFSROFHV-WZGZYPNHSA-N

Cite this record

CBID:72667 http://www.chembase.cn/molecule-72667.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2E)-but-2-enedioic acid bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
IUPAC Traditional name
fumaric acid bis[(isopropoxycarbonyl)oxy]methyl {[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methanephosphonate
fumaric acid; pmpa prodrug
Synonyms
Viread
Tenofovir Disoproxil Fumarate
5-[[(1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]-2,4,6,8-tetraoxa-5-phosphanonanedioic Acid 1,9-Bis(1-methylethyl) Ester 5-Oxide (2E)-2-Butenedioate
GS 4331-05
PMPA Prodrug
Tenofovir DF
Virea
CAS Number
202138-50-9
MDL Number
MFCD08141829
PubChem SID
162037588
PubChem CID
6398764

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 6398764 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 18.587572  H Acceptors 10 
H Donor LogD (pH = 5.5) 2.5019443 
LogD (pH = 7.4) 2.650774  Log P 2.653051 
Molar Refractivity 118.5882 cm3 Polarizability 47.692413 Å3
Polar Surface Area 185.44 Å2 Rotatable Bonds 19 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
113-115°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Target
Reverse transcriptase expand Show data source
Purity
95+% expand Show data source
Salt Data
Fumarate expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals - S1400 external link
Research Area: Infection
Biological Activity:
Tenofovir disoproxil fumarate belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. [1]
Toronto Research Chemicals - T018505 external link
Acyclic phosphonate nucleotide analogue; reverse transcriptase inhibitor. Used as an anti-HIV agent. Antiviral.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.rxlist.com/atripla-drug.htm
  • • Shaw, J.-P., et al.: Pharm. Res., 14, 1824 (1997)
  • • Wyles, D., et al.: Clin Infect. Dis., 40, 174 (1997)
  • • Peng, J., et al.: J. Clin. Pharmacol., 46, 265 (1997)
  • • Seminari, E., et al.: J. Antimicrob. Chemother., 60, 831 (1997)
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PATENTS

PATENTS

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INTERNET

INTERNET

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