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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30N5O10P.C4H4O4
Molecular Weight 635.5149
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR DISOPROXIL MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC(C)OC(=O)OCOP(=O)(CO[C@H](C)CN1C=NC2=C1N=CN=C2N)OCOC(=O)OC(C)C

InChI

InChIKey=VCMJCVGFSROFHV-VIEYUMQNSA-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 C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C19H30N5O10P
Molecular Weight 519.4428
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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).

Originator

Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S2211383512001402

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
58.0 µM [Kd]
3.3 nM [EC50]
3.5 nM [EC50]
0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

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 10:25:12 UTC 2023
Edited
by admin
on Sat Dec 16 10:25:12 UTC 2023
Record UNII
7BI6HE4F8S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR DISOPROXIL MALEATE
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, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Tenofovir disoproxil maleate [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
100000163363
Created by admin on Sat Dec 16 10:25:13 UTC 2023 , Edited by admin on Sat Dec 16 10:25:13 UTC 2023
PRIMARY
FDA UNII
7BI6HE4F8S
Created by admin on Sat Dec 16 10:25:12 UTC 2023 , Edited by admin on Sat Dec 16 10:25:12 UTC 2023
PRIMARY
EVMPD
SUB177587
Created by admin on Sat Dec 16 10:25:12 UTC 2023 , Edited by admin on Sat Dec 16 10:25:12 UTC 2023
PRIMARY
PUBCHEM
86280652
Created by admin on Sat Dec 16 10:25:12 UTC 2023 , Edited by admin on Sat Dec 16 10:25:12 UTC 2023
PRIMARY
CAS
1276030-80-8
Created by admin on Sat Dec 16 10:25:12 UTC 2023 , Edited by admin on Sat Dec 16 10:25:12 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY