U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H14N5O4P
Molecular Weight 287.2123
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR ANHYDROUS

SMILES

C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O

InChI

InChIKey=SGOIRFVFHAKUTI-ZCFIWIBFSA-N
InChI=1S/C9H14N5O4P/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)/t6-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H14N5O4P
Molecular Weight 287.2123
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
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
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 Tue Mar 06 11:23:18 UTC 2018
Edited
by admin
on Tue Mar 06 11:23:18 UTC 2018
Record UNII
W4HFE001U5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR ANHYDROUS
Common Name English
TENOFOVIR [WHO-DD]
Common Name English
TENOFOVIR [INN]
Common Name English
TENOFOVIR [MI]
Common Name English
GS-1275
Code English
PHOSPHONIC ACID, P-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-
Systematic Name English
(R)-9-(2-PHOSPHONOMETHOXYPROPYL)ADENINE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175459
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
NDF-RT N0000009947
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
NDF-RT N0000175462
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
Code System Code Type Description
MERCK INDEX
M10559
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY Merck Index
PUBCHEM
464205
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY SWITZERF
EPA CompTox
147127-20-6
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY
INN
7913
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY
LactMed
147127-20-6
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY
RXCUI
1546017
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY RxNorm
EVMPD
SUB04721MIG
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY
DRUG BANK
DB00300
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY
CAS
147127-20-6
Created by admin on Tue Mar 06 11:23:18 UTC 2018 , Edited by admin on Tue Mar 06 11:23:18 UTC 2018
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
May cause renal toxicity
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY