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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H52N5O5P
Molecular Weight 569.7167
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR EXALIDEX

SMILES

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

InChI

InChIKey=SCTJKHUUZLXJIP-RUZDIDTESA-N
InChI=1S/C28H52N5O5P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-36-19-17-20-38-39(34,35)24-37-25(2)21-33-23-32-26-27(29)30-22-31-28(26)33/h22-23,25H,3-21,24H2,1-2H3,(H,34,35)(H2,29,30,31)/t25-/m1/s1

HIDE SMILES / InChI

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).

Originator

Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S2211383512001402

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIREAD

Approved Use

Tenofovir disoproxil fumarate is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV and HBV infections

Launch Date

2012
Primary
VIREAD

Approved Use

Tenofovir disoproxil fumarate is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV and HBV infections

Launch Date

2012
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine.
1993 Feb
Selective inhibition of HIV-1 reverse transcriptase by an antiviral inhibitor, (R)-9-(2-Phosphonylmethoxypropyl)adenine.
1998 Oct 16
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV.
2010 Jul
Patents

Sample Use Guides

The recommended dose of Ictady (tenofovir disoproxil succinate) for the treatment of HIV or for the treatment of chronic hepatitis B is 245 mg (one tablet) once daily taken orally with food.
Route of Administration: Oral
In Vitro Use Guide
(R)-9-(2-Phosphonylmethoxypropyl)adenine (PMPA known as tenofovir) exerts antiretrovirus activity in MT-4 cells infected with HIV-1 and HIV-2 with EC50 values of 5.9 and 4.9 uM, respectively
Name Type Language
TENOFOVIR EXALIDEX
INN   WHO-DD  
INN  
Official Name English
CMX157
Code English
HDP-TENOFOVIR
Common Name English
tenofovir exalidex [INN]
Common Name English
3-(HEXADECYLOXY)PROPYL HYDROGEN ((((2R)-1-(6-AMINO-9H-PURIN-9-YL)PROPAN-2-YL)OXY)METHYL)PHOSPHONATE
Systematic Name English
CMX-157
Code English
PHOSPHONIC ACID, P-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, MONO(3-(HEXADECYLOXY)PROPYL) ESTER
Systematic Name English
Tenofovir exalidex [WHO-DD]
Common Name English
9-R-(2-(PHOSPHONOMETHOXY)PROPYL)ADENINE
Common Name English
PHOSPHONIC ACID, P-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, MONO(3(HEXADECYLOXY)PROPYL) ESTER
Systematic Name English
PHOSPHONIC ACID, (((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, MONO(3-(HEXADECYLOXY)PROPYL) ESTER
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C97452
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
FDA ORPHAN DRUG 583917
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
Code System Code Type Description
INN
10396
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY
FDA UNII
K7J545MEMA
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY
PUBCHEM
23628250
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY
DRUG BANK
DB14925
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY
NCI_THESAURUS
C152560
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY
SMS_ID
100000174656
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY
CAS
911208-73-6
Created by admin on Sat Dec 16 16:44:16 GMT 2023 , Edited by admin on Sat Dec 16 16:44:16 GMT 2023
PRIMARY