Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H14N5O4P |
Molecular Weight | 287.2127 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]([H])(Cn1cnc2c(N)ncnc21)OCP(=O)(O)O
InChI
InChIKey=SGOIRFVFHAKUTI-ZCFIWIBFSA-N
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1
Molecular Formula | C9H14N5O4P |
Molecular Weight | 287.2127 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
|||
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
Sat Jun 26 03:28:49 UTC 2021
by
admin
on
Sat Jun 26 03:28:49 UTC 2021
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Record UNII |
W4HFE001U5
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Record Status |
Validated (UNII)
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Record Version |
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Common Name | English | ||
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175459
Created by
admin on Sat Jun 26 03:28:50 UTC 2021 , Edited by admin on Sat Jun 26 03:28:50 UTC 2021
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NDF-RT |
N0000175656
Created by
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NDF-RT |
N0000009947
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NDF-RT |
N0000175462
Created by
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NDF-RT |
N0000175459
Created by
admin on Sat Jun 26 03:28:50 UTC 2021 , Edited by admin on Sat Jun 26 03:28:50 UTC 2021
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NDF-RT |
N0000175459
Created by
admin on Sat Jun 26 03:28:50 UTC 2021 , Edited by admin on Sat Jun 26 03:28:50 UTC 2021
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M10559
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PRIMARY | Merck Index | ||
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464205
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147127-20-6
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7913
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1546017
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SUB25192
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C170540
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W4HFE001U5
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SUB04721MIG
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DB00300
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147127-20-6
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Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE |
May cause renal toxicity
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TARGET ORGANISM->INHIBITOR |
EC50
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |