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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29N6O5P
Molecular Weight 476.4659
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR ALAFENAMIDE

SMILES

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=LDEKQSIMHVQZJK-CAQYMETFSA-N
InChI=1S/C21H29N6O5P/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/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/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

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).

CNS Activity

Originator

Chimerix
20
Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S2211383512001402

Approval Year

2001
194
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 58.0 µM [Kd]
Inhibitor
8297
 3.3 nM [EC50]
Inhibitor
8297
 3.5 nM [EC50]
Inhibitor
8297
 0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Approved
8429
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
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
3B Scientific (Wuhan) Corp
3B2-0205
http://www.3bsc.com/index/pro_info.php?id=19561
AA Blocks
AA001EJQ
http://www.aablocks.com/goods/Goods/detail?id=AA001EJQ
AEchem Scientific Corp., USA
AE1-016163
http://www.aechemsc.com/info_products/AE1-016163.php
AHH Chemical co.,ltd
API-1191
http://www.ahhchemical.com/product/API-1191.html
AK Scientific, Inc. (AKSCI)
J90012
http://www.aksci.com/item_detail.php?cat=J90012
Aaron Chemicals
AR001FBI
http://www.aaronchem.com/147127-20-6
AbMole Bioscience
M5051
http://www.abmole.com/products/tenofovir.html
Acorn PharmaTech
ACN-029240
http://www.acornpharmatech.com/
Active Biopharma
ABP000917
http://www.activebiopharma.com/147127-20-6
Adooq BioScience
A10908
https://www.adooq.com/tenofovir-viread.html
Alsachim
1763
http://www.alsachim.com/product-C2530-glo.bal-view.html
Angene
AGN-PC-0PZUPY
http://www.angenechemical.com/productshow/AGN-PC-0PZUPY.html
ApexBio Technology
A5275
http://www.apexbt.com/tenofovir.html
AstaTech, Inc.
34244
http://www.astatechinc.com/CPSResult.php?CRNO=35657
Aurum Pharmatech LLC
S-2389
http://www.Aurumpharmatech.com/Product/ProductDetails/S_2389
AvaChem Scientific
2678
http://www.avachem.com/productSearch.asp?2678
Axon MedChem
3157
https://www.axonmedchem.com/product/3157
BLD Pharm
BD01204701
http://www.bldpharm.com/products/107021-12-5.html
BLD Pharm
BD18435
http://www.bldpharm.com/products/147127-20-6.html
BioCrick
BCC2500
http://www.biocrick.com/Tenofovir-BCC2500.html
BioSynth
Q-201787
https://www.biosynth.com/en/products/life-science/enzyme-substrates-reagents/products/Q-201787.html
Boerchem
BC208449
http://www.boerchem.com/?product_35256.html
CSNpharm
CSN12559
https://www.csnpharm.com/products/tenofovir.html
Capot Chemical
9452
http://www.capotchem.com/en/9452.htm
Capot Chemical
PubChem9452
http://www.capotchem.com/en/9452.htm
Chem Scene
CS-1609
http://www.chemscene.com/147127-20-6.html
ChemMol
1032196
http://www.chemmol.com/chemmol/1032196.html
ChemMol
30108887
http://www.chemmol.com/chemmol/30108887.html
ChemMol
44003255
http://www.chemmol.com/chemmol/44003255.html
ChemMol
97900713
http://www.chemmol.com/chemmol/97900713.html
ChemReagents
80014913
http://www.chemreagents.com/Product/Product.asp?ProductID=80014913
Chemenu
CM110444
http://www.chemenu.com/products/CM110444
Chemspace
CSSB00016987604
https://chem-space.com/CSSB00016987604
Chiralblock Biosciences
CB10985
http://www.chiralblock.com/products/147127-20-6.html
Matrix Scientific
74030
https://www.matrixscientific.com/074030.html
MedChem Express
HY-13910
https://www.medchemexpress.com/tenofovir.html
OChem
5252
http://www.ocheminc.com/index.php?act=psearch&pid=127T206
Oakwood
77792
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=62966&ExtHyperLink=1
Selleck Chemicals
S1401
http://www.selleckchem.com/products/Tenofovir.html
Sigma-Aldrich
SML1795_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/sml1795?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S544915
http://www.smolecule.com/products/s544915
Smolecule
S752291
https://www.smolecule.com/products/s752291
TCI (Tokyo Chemical Industry)
T3006
http://www.tcichemicals.com/eshop/en/us/commodity/T3006/index.html
THE BioTek
bt-284194
https://www.thebiotek.com/product/inhibitors/bt-284194
THE BioTek
bt-293647
https://www.thebiotek.com/product/others/bt-293647
Tocris
3666
https://www.tocris.com/products/tenofovir_3666
Yuhao Chemical
A0500092
http://www.chemyuhao.com/147127-20-6.html
abcr GmbH
AB437841
http://www.abcr.com/shop/en/AB437841
eNovation Chemicals
D320167
http://www.enovationchem.com/productDetails.asp?productID=D320167
eNovation Chemicals
D275770
https://www.enovationchem.com/ProductDetails.asp?ProductID=D275770
iChemical
EBD47973
http://www.ichemical.com/products/147127-20-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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

Patents

20080103115
20
20110021464
20
EP2440560
20
JP2011506374A
20

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:04:36 GMT 2023
Edited
by admin
on Sat Dec 16 06:04:36 GMT 2023
Record UNII
EL9943AG5J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR ALAFENAMIDE
DASH   INN   USAN   WHO-DD  
INN   USAN  
Official Name English
tenofovir alafenamide [INN]
Common Name English
TENOFOVIR ALAFENAMIDE [MI]
Common Name English
GS-734003
Code English
Tenofovir alafenamide [WHO-DD]
Common Name English
L-ALANINE, N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHENOXYPHOSPHINYL)-, 1-METHYLETHYL ESTER
Common Name English
GS-7340
Code English
1-METHYLETHYL N-((S)-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHENOXYPHOSPHINYL)-L-ALANINATE
Systematic Name English
TENOFOVIR ALAFENAMIDE [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AF13
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
EMA ASSESSMENT REPORTS GENVOYA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
WHO-ATC J05AR19
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
EMA ASSESSMENT REPORTS DESCOVY (AUTHORIZED: HIV INFECTIONS )
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
WHO-ATC J05AR22
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
FDA ORPHAN DRUG 569716
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
WHO-ATC J05AR18
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
NCI_THESAURUS C97452
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
WHO-ATC J05AR20
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
Code System Code Type Description
DRUG CENTRAL
4944
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
WIKIPEDIA
Tenofovir alafenamide
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
INN
9980
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
CAS
379270-37-8
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107825
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
FDA UNII
EL9943AG5J
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
EVMPD
SUB121761
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
CHEBI
90926
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
SMS_ID
100000144893
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
DRUG BANK
DB09299
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
RXCUI
1721603
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY RxNorm
DAILYMED
EL9943AG5J
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
NCI_THESAURUS
C148276
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
USAN
ZZ-65
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
MERCK INDEX
m12126
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID50958941
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
PUBCHEM
9574768
Created by admin on Sat Dec 16 06:04:36 GMT 2023 , Edited by admin on Sat Dec 16 06:04:36 GMT 2023
PRIMARY
Related Record Type Details
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of TENOFOVIR ALAFENAMIDE ENANTIOMER
ENANTIOMER -> ENANTIOMER
LIVER CARBOXYLESTERASE 1
METABOLIC ENZYME -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
Structure of TENOFOVIR ALAFENAMIDE FUMARATE
SALT/SOLVATE -> PARENT
Structure of TENOFOVIR ALAFENAMIDE SEBACATE
SALT/SOLVATE -> PARENT
OATP1B1
TRANSPORTER -> SUBSTRATE
OATP-8
TRANSPORTER -> SUBSTRATE
Structure of TENOFOVIR ALAFENAMIDE MONOFUMARATE
SALT/SOLVATE -> PARENT
LYSOSOMAL PROTECTIVE PROTEIN
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of TENOFOVIR ANHYDROUS
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of TENOFOVIR ANHYDROUS
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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