Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C29H40FN5O2.C4H4O4 |
| Molecular Weight | 625.7308 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.CC(C)C(=O)N1CCC2=C(C1)N=C(C)N2[C@@H]3C[C@@H]4CC[C@H](C3)N4CC[C@H](NC(C)=O)C5=CC=CC(F)=C5
InChI
InChIKey=QLJWVEIOTDXIRX-YXFITVAVSA-N
InChI=1S/C29H40FN5O2.C4H4O4/c1-18(2)29(37)33-12-11-28-27(17-33)31-19(3)35(28)25-15-23-8-9-24(16-25)34(23)13-10-26(32-20(4)36)21-6-5-7-22(30)14-21;5-3(6)1-2-4(7)8/h5-7,14,18,23-26H,8-13,15-17H2,1-4H3,(H,32,36);1-2H,(H,5,6)(H,7,8)/b;2-1+/t23-,24+,25+,26-;/m0./s1
| Molecular Formula | C29H40FN5O2 |
| Molecular Weight | 509.6586 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| 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 |
PF-232798 is a potent oral CCR5 antagonist with a primary and selectivity/safety pharmacology profile similar to maraviroc (MVC). PF-232798 shows increased binding affinity and improved oral absorption compared to maraviroc. In addition, it retains activity against a laboratory generated maraviroc-resistant HIV-1 strain, indicating an alternative drug resistance profile. PF-232798 binds to the same pocket as MVC within the transmembrane region of CCR5, but shows additional interactions at the ECL2 hinge region. PF-232798 is well tolerated in normal volunteers. PF-232798 had been in a phase-II clinical trial for the treatment of HIV infections. However, this development was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Anti-HIV agents. Is PF-232798 a possible successor to maraviroc? | 2008 Mar |
|
| An imidazopiperidine series of CCR5 antagonists for the treatment of HIV: the discovery of N-{(1S)-1-(3-fluorophenyl)-3-[(3-endo)-3-(5-isobutyryl-2-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]propyl}acetamide (PF-232798). | 2011 Jan 13 |
|
| Ligand- and mutation-induced conformational selection in the CCR5 chemokine G protein-coupled receptor. | 2014 Sep 9 |
|
| Molecular binding mode of PF-232798, a clinical anti-HIV candidate, at chemokine receptor CCR5. | 2019 Apr |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 04:48:50 GMT 2023
by
admin
on
Sat Dec 16 04:48:50 GMT 2023
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| Record UNII |
8H0Z3KG6OL
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| Record Status |
Validated (UNII)
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| Record Version |
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