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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30N5O10P
Molecular Weight 519.4428
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR DISOPROXIL

SMILES

CC(C)OC(=O)OCOP(=O)(CO[C@H](C)CN1C=NC2=C1N=CN=C2N)OCOC(=O)OC(C)C

InChI

InChIKey=JFVZFKDSXNQEJW-CQSZACIVSA-N
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

HIDE SMILES / InChI

Description

CMX157 is a lipid (1-0-hexadecyloxypropyl) conjugate of the acyclic nucleotide analog tenofovir (TFV) with activity against both wild-type and antiretroviral drug-resistant HIV strains, including multidrug nucleoside/nucleotide analog-resistant viruses. CMX157 was designed to mimic lysophosphatidylcholine to take advantage of natural lipid uptake pathways and to achieve high intracellular concentrations of the active antiviral, with the aim of increasing the effectiveness of TFV against wild-type and mutant HIV. CMX157 demonstrated potential to effectively suppress replication of multiNRTI-resistant (MNR) HIV that cannot be treated with any currently available NRTIs, including TDF. It is in phase II clinical trial for HIV infections in USA and phase Ib portion of the phase I/II trial for Hepatitis B in Thailand (PO).

Originator

Approval Year

2001
80
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
6502
HIV Infections
 3.5 nM [EC50]
Inhibitor
6502
HIV Infections
 3.3 nM [EC50]
Inhibitor
6502
Hepatitis B
 0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HIV-2
HIV-1, subtype A 92RW009
Basic research
Primary
HBV replication
Phase II
1051
PubMed

PubMed

TitleDatePubMed
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV.
2010 Jul
Patents

Patents

20080103115
12
20110021464
12

Sample Use Guides

In Vivo Use Guide
For hepatitis B - 5-100mg tablet
Route of Administration: Oral
In Vitro Use Guide
CMX-157 was active against all major subtypes of HIV-1 and HIV-2 in fresh human peripheral blood mononuclear cells (PBMCs) and against all HIV-1 strains evaluated in monocyte-derived macrophages, with 50% effective concentrations (EC(50)s) ranging between 0.20 and 7.2 nM.
Name Type Language
TENOFOVIR DISOPROXIL
EMA EPAR   WHO-DD  
Common Name English
GS-4331
Code English
TENOFOVIR BIS(ISOPROPYLOXYCARBONYLOXYMETHYL) ESTER [MI]
Common Name English
TENOFOVIR DISOPROXIL [EMA EPAR]
Common Name English
TENOFOVIR BIS(ISOPROPYLOXYCARBONYLOXYMETHYL) ESTER
MI  
Common Name English
STRIBILD COMPONENT TENOFOVIR DISOPROXIL
Brand Name English
BIS-POC-PMPA
Common Name English
TENOFOVIR DISOPROXIL [WHO-DD]
Common Name English
(R)-BIS(POC)PMPA
Common Name English
2,4,6,8-TETRAOXA-5-PHOSPHANONANEDIOIC ACID, 5-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, 1,9-BIS(1-METHYLETHYL) ESTER, 5-OXIDE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QJ05AR09
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
EMA ASSESSMENT REPORTS STRIBILD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AR09
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AR12
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AF07
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-VATC QJ05AR11
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AR11
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-VATC QJ05AR06
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AR06
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AR08
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-VATC QJ05AR03
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-ATC J05AR03
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-VATC QJ05AF07
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
WHO-VATC QJ05AR08
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
Code System Code Type Description
MESH
C418563
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY
EVMPD
SUB20643
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY
WIKIPEDIA
Tenofovir disoproxil
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY
PUBCHEM
5481350
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY SWITZERF
EPA CompTox
201341-05-1
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY
CAS
201341-05-1
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY
MERCK INDEX
M10559
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY Merck Index
RXCUI
300195
Created by admin on Tue Mar 06 11:45:40 UTC 2018 , Edited by admin on Tue Mar 06 11:45:40 UTC 2018
PRIMARY RxNorm
SUBSTANCE RECORD
Structure of TENOFOVIR DISOPROXIL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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