U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30N5O10P.C4H4O4
Molecular Weight 635.5159
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR DISOPROXIL FUMARATE

SMILES

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

InChI

InChIKey=VCMJCVGFSROFHV-WZGZYPNHSA-N
InChI=1S/C19H30N5O10P.C4H4O4/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;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C19H30N5O10P
Molecular Weight 519.4435
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0723
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: HIV-1, subtype A 92RW009
3.3 nM [EC50]
3.5 nM [EC50]
Target ID: HBV replication
0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV.
2010 Jul
Patents

Sample Use Guides

For hepatitis B - 5-100mg tablet
Route of Administration: Oral
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 Fri Jun 25 21:38:41 UTC 2021
Edited
by admin
on Fri Jun 25 21:38:41 UTC 2021
Record UNII
OTT9J7900I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR DISOPROXIL FUMARATE
EMA EPAR   HSDB   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official Name English
TENOFOVIR DISOPROXIL FUMARATE [JAN]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF ODEFSEY
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [HSDB]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF TEMIXYS
Common Name English
GS-4331-05
Code English
TENOFOVIR DISOPROXIL FUMARATE [USAN]
Common Name English
9-((R)-2-((BIS(((ISOPROPOXYCARBONYL)OXY)-METHOXY)PHOSPHINYL)METHOXY)PROPYL)ADENINE FUMARATE (1:1)
Common Name English
TENOFOVIR DF
Common Name English
TENOFOVIR (AS DISOPROXIL FUMARATE)
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [VANDF]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [WHO-DD]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF STRIBILD
Brand Name English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF TRUVADA
Brand Name English
GSK548470
Code English
TENOFOVIR DISOPROXIL FUMARATE [WHO-IP]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF EVIPLERA
Brand Name English
TENOFOVIR DISOPROXIL FUMARATE [MI]
Common Name English
TENOFOVIRI DISOPROXILI FUMARAS [WHO-IP LATIN]
Common Name English
EVIPLERA COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
TENOFOVIR DISOPROXIL FUMARATE [EMA EPAR]
Common Name English
ATRIPLA COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Common Name English
TEMIXYS COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Common Name English
VIREAD
Brand Name English
TENOFOVIR DISOPROXIL FUMARATE [ORANGE BOOK]
Common Name English
GSK-548470
Code English
ODEFSEY COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [MART.]
Common Name English
STRIBILD COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
PMPA-PRODRUG
Code English
TENOFOVIR DISOPROXIL FUMARATE [USP-RS]
Common Name English
BIS(HYDROXYMETHYL) (((R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHOSPHONATE, BIS(ISOPROPYL CARBONATE) (ESTER), FUMARATE (1:1)
Common Name English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF ATRIPLA
Common Name English
DELSTRIGO COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
GS-4331-05-
Code English
PMPA PRODRUG
Code English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT DELSTRIGO
Brand Name English
TRUVADA COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
(R)-5-((2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-2,4,6,8-TETRAOXA-5-PHOSPHANONANEDIOIC ACID, BIS(1-METHYLETHYL) ESTER, 5-OXIDE, (E)-2-BUTENEDIOATE (1:1)
Common Name English
VIREA
Brand Name English
TDF
Common Name English
9-((R)-2-((BIS(((ISOPROPOXYCARBONYL)OXY)METHOXY)PHOSPHINYL)METHOXY)PROPYL)ADENINE FUMARATE (1:1)
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 538416
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
EMA ASSESSMENT REPORTS VIREAD (AUTHORIZED: HEPTATITS B, CHRONIC)
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
NCI_THESAURUS C97452
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
EU-Orphan Drug EU/3/14/1419
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
FDA ORPHAN DRUG 559316
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
EMA ASSESSMENT REPORTS EVIPLERA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
EMA ASSESSMENT REPORTS ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
EMA ASSESSMENT REPORTS TRUVADA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
EMA ASSESSMENT REPORTS VIREAD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
Code System Code Type Description
CAS
202138-50-9
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
USP_CATALOG
1643656
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M10559
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY Merck Index
RXCUI
322248
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY RxNorm
EPA CompTox
202138-50-9
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
TENOFOVIR DISOPROXIL FUMARATE
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY Description: White to almost-white, crystalline powder. Solubility: Slightly soluble in water, soluble in methanol, very slightly soluble in dichloromethane. Category: Antiretroviral (Nucleotide Reverse Transcriptase Inhibitor). Storage: Tenofovir disoproxil fumarate should be kept in a tightly closed container, protected from light and stored at a temperature between 2?8 ?C. Additional information: Tenofovir disoproxil fumarate may exhibit polymorphism. Definition: Tenofovir disoproxil fumarate contains not less than 98.5% and not more than 101.0% of tenofovir disoproxil fumarate(C19H30N5O10P,C4H4O4), calculated with reference to the anhydrous substance. Manufacture: The production method is validated to ensure that the substance, if tested, would comply with: ? a limit of not more than 5 ppm for the mutagenic impurity 9-propenyladenine (impurity K), which may be a synthesis related substance, using a suitable method; ? a limit of not more than 1.0% for the tenofovir disoproxil (S)-enantiomer (impurity G) using a suitable chiral chromatographic method.
NCI_THESAURUS
C47747
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
EVMPD
SUB12607MIG
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
PUBCHEM
6398764
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
DRUG BANK
DBSALT000172
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
FDA UNII
OTT9J7900I
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL1538
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
HSDB
7165
Created by admin on Fri Jun 25 21:38:41 UTC 2021 , Edited by admin on Fri Jun 25 21:38:41 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
IMPURITY -> PARENT
The production method is validated to ensure that the substance, if tested, would comply with: ? a limit of not more than 1.0% for the tenofovir disoproxil (S)-enantiomer (impurity G) using a suitable chiral chromatographic method.
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
Related Record Type Details
ACTIVE MOIETY