Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H29N6O5P |
| Molecular Weight | 476.4659 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)OC(=O)[C@H](C)N[P@@](=O)(CO[C@H](C)CN1C=NC2=C(N)N=CN=C12)OC3=CC=CC=C3
InChI
InChIKey=LDEKQSIMHVQZJK-GNGHXOLXSA-N
InChI=1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33-/m1/s1
| Molecular Formula | C21H29N6O5P |
| Molecular Weight | 476.4659 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator'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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL247 |
58.0 µM [Kd] | ||
Target ID: HIV-1, subtype A 92RW009 |
3.3 nM [EC50] | ||
Target ID: HIV-2 |
3.5 nM [EC50] | ||
Target ID: HBV replication |
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 Date1.32675836E12 |
|||
| 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 Date1.32675836E12 |
|||
| 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
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
| Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 12:51:16 UTC 2023
by
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Sat Dec 16 12:51:16 UTC 2023
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| Record UNII |
J4414G3BUK
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| Record Status |
Validated (UNII)
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admin on Sat Dec 16 12:51:16 UTC 2023 , Edited by admin on Sat Dec 16 12:51:16 UTC 2023
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