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Tenofovir Disoproxil Fumarate

PAPER

The current three-step manufacturing route for the preparation of tenofovir disoproxil fumarate (1) was assessed and optimized leading to a higher yielding, simpler, and greener process. Key improvements in the process route include the refinement of the second stage through the replacement of the problematic magnesium tert-butoxide (MTB) with a 1:1 ratio of a Grignard reagent and tert-butanol. The development of a virtually solvent-free approach and the establishment of a workup and purification protocol which allows the isolation of a pure diethyl phosphonate ester (8) was achieved

see………….http://pubs.acs.org/doi/abs/10.1021/acs.oprd.5b00364

An Improved Process for the Preparation of Tenofovir Disoproxil Fumarate

• University of Pretoria

  Department of Chemistry

  Pretoria, South Africa

Department of Chemistry, Natural and Agricultural Sciences, University of Pretoria, 2 Lynnwood Road, Hatfield, 0002, Gauteng, South Africa

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enofovir disoproxil

Systematic (IUPAC) name
Bis{[(isopropoxycarbonyl)oxy]methyl} ({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosphonate
Clinical data
Trade names	Viread
AHFS/Drugs.com	monograph
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Oral (tablets)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	25%
Identifiers
CAS Number	201341-05-1
ATC code	J05AF07 (WHO)
PubChem	CID 5481350
ChemSpider	4587262
UNII	F4YU4LON7I
ChEBI	CHEBI:63717
NIAID ChemDB	080741
Chemical data
Formula	C19H30N5O10P
Molar mass	519.443 g/mol
SMILES[show]
InChI[show]

Tenofovir

Systematic (IUPAC) name
({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
Clinical data
MedlinePlus	a602018
Routes of administration	In form of prodrugs
Pharmacokinetic data
Protein binding	< 1%
Biological half-life	17 hours
Excretion	Renal
Identifiers
CAS Number	147127-20-6
ATC code	None
PubChem	CID 464205
DrugBank	DB00300
ChemSpider	408154
UNII	99YXE507IL
KEGG	D06074
ChEBI	CHEBI:63625
ChEMBL	CHEMBL483
Synonyms	9-(2-Phosphonyl-methoxypropyly)adenine (PMPA)
Chemical data
Formula	C9H14N5O4P
Molar mass	287.213 g/mol