TENOFOVIR ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H14N5O4P
Molecular Weight	287.2123
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](CN1C=NC2=C1N=CN=C2N)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	287.2123
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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
HIV-2 12	Inhibitor 6502	HIV Infections	3.5 nM [EC50]
HIV-1, subtype A 92RW009 12	Inhibitor 6502	HIV Infections	3.3 nM [EC50]
HBV replication 12	Inhibitor 6502	Hepatitis B	0.49 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV Infections 125	Primary	HIV-2 HIV-1, subtype A 92RW009	Basic research
Hepatitis B 35	Primary	HBV replication	Phase II 1051

PubMed

Title	Date	PubMed

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 `Tue Mar 06 11:23:18 UTC 2018` Edited by `admin` on `Tue Mar 06 11:23:18 UTC 2018`
Record UNII	W4HFE001U5
Record Status	`Validated (UNII)`
Record Version

Download

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