TENOFOVIR ALAFENAMIDE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452366https://www.ncbi.nlm.nih.gov/pubmed/20439609
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Human immunodeficiency virus type 1 reverse transcriptase 67 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9765248	Inhibitor 8297	58.0 µM [Kd]
HIV-1, subtype A 92RW009 20 Target ID: HIV-1, subtype A 92RW009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Inhibitor 8297	3.3 nM [EC50]
HIV-2 20 Target ID: HIV-2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Inhibitor 8297	3.5 nM [EC50]
HBV replication 20 Target ID: HBV replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/17646420	Inhibitor 8297	0.49 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
HIV-1 infection 151 Sources: https://aidsinfo.nih.gov/drugs/290/tenofovir-disoproxil-fumarate/0/patient	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 1.32675836E12
HBV infections 20 Sources: https://aidsinfo.nih.gov/drugs/290/tenofovir-disoproxil-fumarate/0/patient	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 1.32675836E12
Hepatitis B 57 Sources: https://clinicaltrials.gov/ct2/show/NCT02710604	Primary	Phase II 1132	Unknown Approved Use Unknown
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Primary	Basic research	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
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	8452366
Selective inhibition of HIV-1 reverse transcriptase by an antiviral inhibitor, (R)-9-(2-Phosphonylmethoxypropyl)adenine.	1998 Oct 16	9765248
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV.	2010 Jul	20439609

Patents

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 UTC 2023` Edited by `admin` on `Sat Dec 16 06:04:36 UTC 2023`
Record UNII	EL9943AG5J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TENOFOVIR ALAFENAMIDE

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