TENOFOVIR DISOPROXIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30N5O10P
Molecular Weight	519.4435
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)OCOP(=O)(CO[C@]([H])(C)Cn1cnc2c(N)ncnc21)OCOC(=O)OC(C)C

InChI

InChIKey=JFVZFKDSXNQEJW-CQSZACIVSA-N

InChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1

HIDE SMILES / InChI

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.

Name

Type

Language

TENOFOVIR DISOPROXIL

Common Name

English

GS-4331

Code

English

TELURA COMPONENT OF TENOFOVIR DISOPROXIL

Common Name

English

TENOFOVIR BIS(ISOPROPYLOXYCARBONYLOXYMETHYL) ESTER [MI]

Common Name

English

TENOFOVIR DISOPROXIL [EMA EPAR]

Common Name

English

TENOFOVIR BIS(ISOPROPYLOXYCARBONYLOXYMETHYL) ESTER

Common Name

English

STRIBILD COMPONENT TENOFOVIR DISOPROXIL

Brand Name

English

BIS-POC-PMPA

Common Name

English

TENOFOVIR DISOPROXIL [WHO-DD]

Common Name

English

(R)-BIS(POC)PMPA

Common Name

English

2,4,6,8-TETRAOXA-5-PHOSPHANONANEDIOIC ACID, 5-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, 1,9-BIS(1-METHYLETHYL) ESTER, 5-OXIDE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QJ05AR09

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

EMA ASSESSMENT REPORTS

STRIBILD (AUTHORIZED: HIV INFECTIONS)

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR24

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR09

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR12

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AF07

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-VATC

QJ05AR11

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR11

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-VATC

QJ05AR06

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR06

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR08

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-VATC

QJ05AR03

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-ATC

J05AR03

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-VATC

QJ05AF07

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

WHO-VATC

QJ05AR08

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

Code System Code Type Description

DRUG BANK

DB00300

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

DRUG CENTRAL

2593

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

MESH

C418563

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

EVMPD

SUB20643

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

WIKIPEDIA

Tenofovir disoproxil

Created by admin on Sat Jun 26 10:30:16 UTC 2021 , Edited by admin on Sat Jun 26 10:30:16 UTC 2021

PRIMARY

PUBCHEM

5481350

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

EPA CompTox

201341-05-1

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

CAS

201341-05-1

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

MERCK INDEX

M10559

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

Merck Index

FDA UNII

F4YU4LON7I

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

RXCUI

300195

Created by admin on Sat Jun 26 10:30:15 UTC 2021 , Edited by admin on Sat Jun 26 10:30:15 UTC 2021

PRIMARY

RxNorm

ACTIVE MOIETY


					W4HFE001U5

TENOFOVIR ANHYDROUS

SALT/SOLVATE (PARENT)


					2D4WI76OMK

TENOFOVIR DISOPROXIL OROTATE

SALT/SOLVATE (PARENT)


					F06G7ZBB70

TENOFOVIR DISOPROXIL ASPARTATE

SALT/SOLVATE (PARENT)


					7BI6HE4F8S

TENOFOVIR DISOPROXIL MALEATE

SALT/SOLVATE (PARENT)


					05F4G8DO5I

TENOFOVIR DISOPROXIL PHOSPHATE

SALT/SOLVATE (PARENT)


					OTT9J7900I

TENOFOVIR DISOPROXIL FUMARATE

SUBSTANCE RECORD


					F4YU4LON7I

TENOFOVIR DISOPROXIL

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20439609Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/20439609 and http://ir.chimerix.com/releasedetail.cfm?releaseid=752310

Originator

Approval Year

Targets

Conditions

PubMed

Patents

Sample Use Guides

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