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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29N6O5P.C4H4O4
Molecular Weight 592.5381
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR ALAFENAMIDE MONOFUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CC(C)OC(=O)[C@H](C)N[P@](=O)(CO[C@H](C)CN1C=NC2=C(N)N=CN=C12)OC3=CC=CC=C3

InChI

InChIKey=MEJAFWXKUKMUIR-FHPNUNMMSA-N
InChI=1S/C21H29N6O5P.C4H4O4/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;5-3(6)1-2-4(7)8/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-2H,(H,5,6)(H,7,8)/b;2-1+/t15-,16+,33+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C21H29N6O5P
Molecular Weight 476.4659
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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
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 Thu Jul 06 18:26:22 UTC 2023
Edited
by admin
on Thu Jul 06 18:26:22 UTC 2023
Record UNII
H2S5S51WW6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR ALAFENAMIDE MONOFUMARATE
Common Name English
Tenofovir alafenamide monofumarate [WHO-DD]
Common Name English
L-ALANINE, N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHENOXYPHOSPHINYL)-, 1-METHYLETHYL ESTER, (2E)-2-BUTENEDIOATE (1:1)
Systematic Name English
GS-7340 MONOFUMARATE
Code English
Code System Code Type Description
FDA UNII
H2S5S51WW6
Created by admin on Thu Jul 06 18:26:22 UTC 2023 , Edited by admin on Thu Jul 06 18:26:22 UTC 2023
PRIMARY
PUBCHEM
68516365
Created by admin on Thu Jul 06 18:26:22 UTC 2023 , Edited by admin on Thu Jul 06 18:26:22 UTC 2023
PRIMARY
CAS
379270-38-9
Created by admin on Thu Jul 06 18:26:22 UTC 2023 , Edited by admin on Thu Jul 06 18:26:22 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY