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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29N6O5P
Molecular Weight 476.4659
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR ALAFENAMIDE

SMILES

CC(C)OC(=O)[C@H](C)N[P@@](=O)(CO[C@H](C)CN1C=NC2=C1N=CN=C2N)OC3=CC=CC=C3

InChI

InChIKey=LDEKQSIMHVQZJK-GNGHXOLXSA-N
InChI=1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33-/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H29N6O5P
Molecular Weight 476.4659
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [EC50]
3.3 nM [EC50]
0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
PubMed

PubMed

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

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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:20:03 UTC 2019
Edited
by admin
on Mon Oct 21 21:20:03 UTC 2019
Record UNII
EL9943AG5J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR ALAFENAMIDE
DASH   INN   USAN   WHO-DD  
INN   USAN  
Official Name English
TENOFOVIR ALAFENAMIDE [INN]
Common Name English
TENOFOVIR ALAFENAMIDE [WHO-DD]
Common Name English
GS-734003
Code English
TENOFOVIR ALAFENAMIDE COMPONENT OF BIKTARVY
Brand Name English
L-ALANINE, N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHENOXYPHOSPHINYL)-, 1-METHYLETHYL ESTER
Common Name English
GS-7340
Code English
1-METHYLETHYL N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHENOXYPHOSPHINYL)-L-ALANINATE
Systematic Name English
BIKTARVY COMPONENT TENOFOVIR ALAFENAMIDE
Brand Name English
TENOFOVIR ALAFENAMIDE [USAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 569716
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
WHO-ATC J05AF13
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
EMA ASSESSMENT REPORTS GENVOYA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
WHO-ATC J05AR19
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
EMA ASSESSMENT REPORTS DESCOVY (AUTHORIZED: HIV INFECTIONS )
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
WHO-ATC J05AR22
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
WHO-ATC J05AR18
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
NCI_THESAURUS C97452
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
NCI_THESAURUS C281
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
WHO-ATC J05AR20
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
Code System Code Type Description
WIKIPEDIA
Tenofovir alafenamide
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
INN
9980
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
CAS
379270-37-8
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
ChEMBL
CHEMBL2107825
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
EVMPD
SUB121761
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
DRUG BANK
DB09299
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
RXCUI
1721603
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C148276
Created by admin on Mon Oct 21 21:20:03 UTC 2019 , Edited by admin on Mon Oct 21 21:20:03 UTC 2019
PRIMARY
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