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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21ClN5O4P.C4H4O4
Molecular Weight 553.889
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Hepenofovir fumarate

SMILES

OC(=O)\C=C\C(O)=O.C[C@H](CN1C=NC2=C1N=CN=C2N)OC[P@@]3(=O)OCC[C@H](O3)C4=CC(Cl)=CC=C4

InChI

InChIKey=VLXCMWQJGQKIAD-MXVFSTPESA-N
InChI=1S/C18H21ClN5O4P.C4H4O4/c1-12(8-24-10-23-16-17(20)21-9-22-18(16)24)26-11-29(25)27-6-5-15(28-29)13-3-2-4-14(19)7-13;5-3(6)1-2-4(7)8/h2-4,7,9-10,12,15H,5-6,8,11H2,1H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t12-,15+,29-;/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 C18H21ClN5O4P
Molecular Weight 437.817
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
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

2012
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

2012
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 19:27:56 GMT 2023
Edited
by admin
on Sat Dec 16 19:27:56 GMT 2023
Record UNII
29E2UZ8D7C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Hepenofovir fumarate
Common Name English
9H-Purin-6-amine, 9-[(2R)-2-[[(2R,4S)-4-(3-chlorophenyl)-2-oxido-1,3,2-dioxaphosphorinan-2-yl]methoxy]propyl]-, (2E)-2-butenedioate (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
29E2UZ8D7C
Created by admin on Sat Dec 16 19:27:56 GMT 2023 , Edited by admin on Sat Dec 16 19:27:56 GMT 2023
PRIMARY
PUBCHEM
164512951
Created by admin on Sat Dec 16 19:27:56 GMT 2023 , Edited by admin on Sat Dec 16 19:27:56 GMT 2023
PRIMARY
CAS
1799797-57-1
Created by admin on Sat Dec 16 19:27:56 GMT 2023 , Edited by admin on Sat Dec 16 19:27:56 GMT 2023
PRIMARY
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