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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31N6O5P
Molecular Weight 490.4934
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR AMIBUFENAMIDE

SMILES

CC(C)OC(=O)C(C)(C)N[P@@](=O)(CO[C@]([H])(C)Cn1cnc2c(N)ncnc21)Oc3ccccc3

InChI

InChIKey=ORHSFGJQGPUCRR-JTJFVBHCSA-N
InChI=1S/C22H31N6O5P/c1-15(2)32-21(29)22(4,5)27-34(30,33-17-9-7-6-8-10-17)14-31-16(3)11-28-13-26-18-19(23)24-12-25-20(18)28/h6-10,12-13,15-16H,11,14H2,1-5H3,(H,27,30)(H2,23,24,25)/t16-,34-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H31N6O5P
Molecular Weight 490.4934
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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 06:26:40 UTC 2021
Edited
by admin
on Sat Jun 26 06:26:40 UTC 2021
Record UNII
SGK6176ZDO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR AMIBUFENAMIDE
INN  
Official Name English
ALANINE, N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHENOXYPHOSPHINYL)-2-METHYL-, 1-METHYLETHYL ESTER
Systematic Name English
TENOFOVIR AMIBUFENAMIDE [INN]
Common Name English
Code System Code Type Description
FDA UNII
SGK6176ZDO
Created by admin on Sat Jun 26 06:26:40 UTC 2021 , Edited by admin on Sat Jun 26 06:26:40 UTC 2021
PRIMARY
PUBCHEM
118214142
Created by admin on Sat Jun 26 06:26:40 UTC 2021 , Edited by admin on Sat Jun 26 06:26:40 UTC 2021
PRIMARY
INN
11454
Created by admin on Sat Jun 26 06:26:40 UTC 2021 , Edited by admin on Sat Jun 26 06:26:40 UTC 2021
PRIMARY
NCI_THESAURUS
C175861
Created by admin on Sat Jun 26 06:26:40 UTC 2021 , Edited by admin on Sat Jun 26 06:26:40 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY