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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H14N5O4P.H2O
Molecular Weight 305.228
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR

SMILES

C[C@]([H])(Cn1cnc2c(N)ncnc21)OCP(=O)(O)O.O

InChI

InChIKey=PINIEAOMWQJGBW-FYZOBXCZSA-N
InChI=1S/C9H14N5O4P.H2O/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);1H2/t6-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C9H14N5O4P
Molecular Weight 287.2127
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20439609 and http://ir.chimerix.com/releasedetail.cfm?releaseid=752310

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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: HIV-1, subtype A 92RW009
3.3 nM [EC50]
3.5 nM [EC50]
Target ID: HBV replication
0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

For hepatitis B - 5-100mg tablet
Route of Administration: Oral
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 Sat Jun 26 05:51:24 UTC 2021
Edited
by admin
on Sat Jun 26 05:51:24 UTC 2021
Record UNII
99YXE507IL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR
MART.   USAN   USP-RS   VANDF  
USAN  
Official Name English
PMPA
Code English
(((R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHOSPHONIC ACID, MONOHYDRATE
Common Name English
TENOFOVIR [USAN]
Common Name English
TENOFOVIR [VANDF]
Common Name English
(R)-((2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHOSPHONIC ACID MONOHYDRATE
Systematic Name English
9-((R)-2-PHOSPHONOMETHOXY-PROPYL)ADENINE MONOHYDRATE
Systematic Name English
PHOSPHONIC ACID, P-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, HYDRATE (1:1)
Systematic Name English
TENOFOVIR MONOHYDRATE
Common Name English
PMP-A
Code English
TENOFOVIR [MART.]
Common Name English
GS-1278
Code English
TENOFOVIR HYDRATE
Common Name English
TENOFOVIR [USP-RS]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AR11
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (FTC/TEN)
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
WHO-ATC J05AR18
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
NDF-RT N0000175656
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
NCI_THESAURUS C97452
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
FDA ORPHAN DRUG 276209
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (EFV/FTC/TEN)
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
NDF-RT N0000175462
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
LIVERTOX 935
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
WHO-ATC J05AR03
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
NCI_THESAURUS C1556
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
WHO-ATC J05AR17
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2592
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
EVMPD
SUB25433
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
NCI_THESAURUS
C29490
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
LACTMED
Tenofovir
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
FDA UNII
99YXE507IL
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
USP_CATALOG
1643601
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL1538
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL483
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
WIKIPEDIA
TENOFOVIR
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
MESH
C096918
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
DRUG BANK
DB14126
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
MESH
C046573
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
RXCUI
117466
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY RxNorm
CAS
206184-49-8
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
PUBCHEM
21146529
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
EVMPD
SUB04721MIG
Created by admin on Sat Jun 26 05:51:24 UTC 2021 , Edited by admin on Sat Jun 26 05:51:24 UTC 2021
PRIMARY
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