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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29N6O5P.C10H18O4
Molecular Weight 678.7147
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR ALAFENAMIDE SEBACATE

SMILES

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

InChI

InChIKey=VSQBAQCLBQQMOO-HCHUQKDBSA-N
InChI=1S/C21H29N6O5P.C10H18O4/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;11-9(12)7-5-3-1-2-4-6-8-10(13)14/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-8H2,(H,11,12)(H,13,14)/t15-,16+,33-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C10H18O4
Molecular Weight 202.2479
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H29N6O5P
Molecular Weight 476.4667
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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
3.29999999999999982 nM [EC50]
3.5 nM [EC50]
Target ID: HBV replication
0.489999999999999991 µM [EC50]
Conditions
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 01:22:37 UTC 2021
Edited
by admin
on Sat Jun 26 01:22:37 UTC 2021
Record UNII
5HP2CJM5GF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR ALAFENAMIDE SEBACATE
Common Name English
TENOFOVIR ALAFENAMIDE SEBACATE [WHO-DD]
Common Name English
Code System Code Type Description
CAS
2241677-49-4
Created by admin on Sat Jun 26 01:22:37 UTC 2021 , Edited by admin on Sat Jun 26 01:22:37 UTC 2021
PRIMARY
PUBCHEM
139593426
Created by admin on Sat Jun 26 01:22:37 UTC 2021 , Edited by admin on Sat Jun 26 01:22:37 UTC 2021
PRIMARY
FDA UNII
5HP2CJM5GF
Created by admin on Sat Jun 26 01:22:37 UTC 2021 , Edited by admin on Sat Jun 26 01:22:37 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY