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
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
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 |
DescriptionSources: https://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/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).
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 |
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 | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02710604
For hepatitis B - 5-100mg tablet
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609
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
Edited
Fri Jun 25 21:38:41 UTC 2021
by
admin
on
Fri Jun 25 21:38:41 UTC 2021
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Record UNII |
OTT9J7900I
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
538416
Created by
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EMA ASSESSMENT REPORTS |
VIREAD (AUTHORIZED: HEPTATITS B, CHRONIC)
Created by
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NCI_THESAURUS |
C97452
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EU-Orphan Drug |
EU/3/14/1419
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FDA ORPHAN DRUG |
559316
Created by
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EMA ASSESSMENT REPORTS |
EVIPLERA (AUTHORIZED: HIV INFECTIONS)
Created by
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EMA ASSESSMENT REPORTS |
ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by
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EMA ASSESSMENT REPORTS |
TRUVADA (AUTHORIZED: HIV INFECTIONS)
Created by
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.1
Created by
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EMA ASSESSMENT REPORTS |
VIREAD (AUTHORIZED: HIV INFECTIONS)
Created by
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Code System | Code | Type | Description | ||
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202138-50-9
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PRIMARY | |||
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1643656
Created by
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PRIMARY | USP-RS | ||
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M10559
Created by
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PRIMARY | Merck Index | ||
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322248
Created by
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PRIMARY | RxNorm | ||
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202138-50-9
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PRIMARY | |||
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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
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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. | ||
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C47747
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SUB12607MIG
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6398764
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DBSALT000172
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OTT9J7900I
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CHEMBL1538
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7165
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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METABOLITE ACTIVE -> PRODRUG |
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
Amount Not Specified
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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.
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
Amount Not Specified
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IMPURITY -> PARENT |
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ACTIVE MOIETY |