TENOFOVIR ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H14N5O4P
Molecular Weight	287.2127
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]([H])(Cn1cnc2c(N)ncnc21)OCP(=O)(O)O

InChI

InChIKey=SGOIRFVFHAKUTI-ZCFIWIBFSA-N

InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C9H14N5O4P
Molecular Weight	287.2127
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Target ID: HIV-1, subtype A 92RW009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Inhibitor 7701	HIV-1 infection	3.29999999999999982 nM [EC50]
Target ID: HIV-2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Inhibitor 7701	HIV-1 infection	3.5 nM [EC50]
Target ID: HBV replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/17646420	Inhibitor 7701	Hepatitis B	0.489999999999999991 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis B 52 Sources: https://clinicaltrials.gov/ct2/show/NCT02710604	Primary		Phase II
HIV-1 infection 140 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Primary		Basic research

PubMed

Title	Date	PubMed
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

For hepatitis B - 5-100mg tablet

Route of Administration: Oral

In Vitro Use Guide

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 03:28:49 UTC 2021` Edited by `admin` on `Sat Jun 26 03:28:49 UTC 2021`
Record UNII	W4HFE001U5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TENOFOVIR ANHYDROUS

Common Name

English

TENOFOVIR [WHO-DD]

Common Name

English

TENOFOVIR [INN]

Common Name

English

TENOFOVIR [MI]

Common Name

English

GS-1275

Code

English

PHOSPHONIC ACID, P-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-

Systematic Name

English

(R)-9-(2-PHOSPHONOMETHOXYPROPYL)ADENINE

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000175459