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
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-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
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 |
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8452366https://www.ncbi.nlm.nih.gov/pubmed/20439609Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452366https://www.ncbi.nlm.nih.gov/pubmed/20439609
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).
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452366http://adisinsight.springer.com/drugs/800020504
Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S2211383512001402
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9765248 |
58.0 µM [Kd] | ||
Target ID: HIV-1, subtype A 92RW009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609 |
3.3 nM [EC50] | ||
Target ID: HIV-2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609 |
3.5 nM [EC50] | ||
Target ID: HBV replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/17646420 |
0.49 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VIREAD Approved UseTenofovir 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 Date2012 |
|||
Primary | VIREAD Approved UseTenofovir 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 Date2012 |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine. | 1993 Feb |
|
Selective inhibition of HIV-1 reverse transcriptase by an antiviral inhibitor, (R)-9-(2-Phosphonylmethoxypropyl)adenine. | 1998 Oct 16 |
|
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV. | 2010 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: http://db.cbg-meb.nl/IB-teksten/h117062_fsuk.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8452366
(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
Edited
Fri Dec 15 15:28:20 GMT 2023
by
admin
on
Fri Dec 15 15:28:20 GMT 2023
|
Record UNII |
OTT9J7900I
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
EMA ASSESSMENT REPORTS |
VIREAD (AUTHORIZED: HEPTATITS B, CHRONIC)
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
NCI_THESAURUS |
C97452
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
EU-Orphan Drug |
EU/3/14/1419
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
EVIPLERA (AUTHORIZED: HIV INFECTIONS)
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
FDA ORPHAN DRUG |
538416
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
FDA ORPHAN DRUG |
559316
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
TRUVADA (AUTHORIZED: HIV INFECTIONS)
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
6.4.2.1
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
VIREAD (AUTHORIZED: HIV INFECTIONS)
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
202138-50-9
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
m10559
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | Merck Index | ||
|
63717
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
322248
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | RxNorm | ||
|
DTXSID5050426
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
TENOFOVIR DISOPROXIL FUMARATE
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
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. | ||
|
OTT9J7900I
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
C47747
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
SUB12607MIG
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
100000092141
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
6398764
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
63718
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
KK-89
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
DBSALT000172
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
1643656
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
OTT9J7900I
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
CHEMBL1538
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY | |||
|
7165
Created by
admin on Fri Dec 15 15:28:20 GMT 2023 , Edited by admin on Fri Dec 15 15:28:20 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
In the chromatogram obtained with solution (1) the area of any peak due to tenofovir monosoproxil (impurity A) is not greater than twice the area of the principal peak obtained with solution (2) (1.0%).
|
||
|
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 |
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
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.
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
Amount Not Specified
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|