| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H41N3O10S2 |
| Molecular Weight | 703.823 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](CC3=CC=C(OCC4=CSC(C)=N4)C=C3)[C@H](O)CN(CC(C)C)S(=O)(=O)C5=CC=C6OCOC6=C5
InChI
InChIKey=JORVRJNILJXMMG-OLNQLETPSA-N
InChI=1S/C33H41N3O10S2/c1-20(2)14-36(48(39,40)25-8-9-29-30(13-25)45-19-44-29)15-28(37)27(35-33(38)46-31-17-43-32-26(31)10-11-41-32)12-22-4-6-24(7-5-22)42-16-23-18-47-21(3)34-23/h4-9,13,18,20,26-28,31-32,37H,10-12,14-17,19H2,1-3H3,(H,35,38)/t26-,27-,28+,31-,32+/m0/s1
| Molecular Formula | C33H41N3O10S2 |
| Molecular Weight | 703.823 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Brecanavir (previously known as VX-385), a HIV aspartyl protease inhibitor was developed for the treatment of HIV. The inhibition of HIV viral proteinase enzyme prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles. Brecanavir reached Phase II development. However, GlaxoSmithKline announced to discontinue development brecanavir. Because of the inability to develop a viable oral dosage formulation capable of delivering the desired brecanavir levels in patients with multi-drug resistant HIV.
Originator
Approval Year
PubMed
Sample Use Guides
In part 1 of the study, single oral doses of Brecanavir (BCV) ranged from 25 mg to 800 mg. In part 2, single oral doses of BCV ranged from 10 mg to 300 mg and were coadministered with 100-mg oral ritonavir (RTV) soft gel capsules. Single doses of BCV and BCV/RTV were generally well tolerated. There were no severe adverse events (SAEs), and no subject was withdrawn due to BCV.
Route of Administration:
Oral
