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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C21H29N6O5P.C4H4O4
Molecular Weight 1069.0058
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR ALAFENAMIDE FUMARATE

SMILES

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

InChI

InChIKey=SVUJNSGGPUCLQZ-LVWWUONPSA-N
InChI=1S/2C21H29N6O5P.C4H4O4/c2*1-14(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/h2*5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*15-,16+,33-;/m11./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0723
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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 02:59:55 UTC 2021
Edited
by admin
on Sat Jun 26 02:59:55 UTC 2021
Record UNII
FWF6Q91TZO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR ALAFENAMIDE FUMARATE
USAN   WHO-DD  
USAN  
Official Name English
ODEFSEY COMPONENT TENOFOVIR ALAFENAMIDE FUMARATE
Brand Name English
GS-7340 HEMIFUMARATE
Code English
GS-7340-03
Code English
TENOFOVIR ALAFENAMIDE FUMARATE [WHO-DD]
Common Name English
TENOFOVIR ALAFENAMIDE FUMARATE (2:1)
Common Name English
SYMTUZA COMPONENT TENOFOVIR ALAFENAMIDE FUMARATE
Brand Name English
TENOFOVIR ALAFENAMIDE FUMARATE COMPONENT OF SYMTUZA
Brand Name English
DESCOVY COMPONENT TENOFOVIR ALAFENAMIDE FUMARATE
Brand Name English
VEMLIDY
Brand Name English
1-METHYLETHYL N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL(PHENOXYPHOSPHINOYL)-L-ALANINATE, (2E)-2-BUTENEDIOATE
Common Name English
TAF
Common Name English
TENOFOVIR ALAFENAMIDE HEMIFUMARATE
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 (2:1)
Common Name English
TENOFOVIR ALAFENAMIDE FUMARATE COMPONENT OF ODEFSEY
Brand Name English
TENOFOVIR ALAFENAMIDE FUMARATE [ORANGE BOOK]
Common Name English
TENOFOVIR ALAFENAMIDE FUMARATE [USAN]
Common Name English
TENOFOVIR ALAFENAMIDE FUMARATE [MI]
Common Name English
TENOFOVIR ALAFENAMIDE FUMARATE COMPONENT OF GENVOYA
Brand Name English
TENOFOVIR ALAFENAMIDE FUMARATE COMPONENT OF DESCOVY
Brand Name English
TENOFOVIR ALAFENAMIDE FUMARATE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
NCI_THESAURUS C97452
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
Code System Code Type Description
PUBCHEM
71511838
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
MERCK INDEX
M12126
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
NCI_THESAURUS
C152559
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107825
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
EVMPD
SUB178389
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
FDA UNII
FWF6Q91TZO
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
CAS
1392275-56-7
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
DRUG BANK
DBSALT002533
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
WIKIPEDIA
TENOFOVIR ALAFENAMIDE FUMARATE
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY
RXCUI
1721604
Created by admin on Sat Jun 26 02:59:55 UTC 2021 , Edited by admin on Sat Jun 26 02:59:55 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY