Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H44N4O6S |
| Molecular Weight | 624.791 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)N[C@@H](C(C1=CC=CC=C1)C2=CC=CC=C2)C(=O)NCCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C3=CC=C(N)C=C3
InChI
InChIKey=QAHLFXYLXBBCPS-IZEXYCQBSA-N
InChI=1S/C33H44N4O6S/c1-24(2)22-37(44(41,42)29-19-17-27(34)18-20-29)28(23-38)16-10-11-21-35-32(39)31(36-33(40)43-3)30(25-12-6-4-7-13-25)26-14-8-5-9-15-26/h4-9,12-15,17-20,24,28,30-31,38H,10-11,16,21-23,34H2,1-3H3,(H,35,39)(H,36,40)/t28-,31-/m0/s1
| Molecular Formula | C33H44N4O6S |
| Molecular Weight | 624.791 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:35:48 UTC 2023
by
admin
on
Sat Dec 16 11:35:48 UTC 2023
|
| Record UNII |
JRI5GOF0K0
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
JRI5GOF0K0
Created by
admin on Sat Dec 16 11:35:48 UTC 2023 , Edited by admin on Sat Dec 16 11:35:48 UTC 2023
|
PRIMARY | |||
|
DB05961
Created by
admin on Sat Dec 16 11:35:48 UTC 2023 , Edited by admin on Sat Dec 16 11:35:48 UTC 2023
|
PRIMARY | |||
|
513956
Created by
admin on Sat Dec 16 11:35:48 UTC 2023 , Edited by admin on Sat Dec 16 11:35:48 UTC 2023
|
PRIMARY | |||
|
612547-11-2
Created by
admin on Sat Dec 16 11:35:48 UTC 2023 , Edited by admin on Sat Dec 16 11:35:48 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
TARGET ORGANISM->INHIBITOR |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ACTIVE MOIETY |
In the present study, we compared the antiviral activity of PL-100 against HIV-1 subtype B with that of darunavir. We used tissue culture experiments to evaluate the in vitro development of resistance to PL-100 and tested the antiviral activity of several clinically approved PIs against PL-100-selected resistant variants. Structural modelling was also used to compare the binding of PL-100 and darunavir to the HIV-1 protease (PR) enzyme.PL-100-resistant variants that emerged within 8-48 weeks showed low- to high-level resistance (3.5- to 21.6-fold) to PL-100, but commonly retained susceptibility to darunavir, which, in contrast, did not select for resistance mutations over a period of 40 weeks. Hydrogen-bonding contacts and the di-THF group in darunavir, as well as the hydrophobic nature of PL-100, contribute to PI binding and a high genetic barrier for resistance. Redesigning the structure of PL-100 to include a di-THF group might improve it.
|
||
|
ACTIVE MOIETY |
A selection for resistance against PL-100 in cord blood mononuclear cells was performed, using the laboratory-adapted IIIb strain of HIV-1, and it was shown that resistance appears to develop slower against this compound than against amprenavir, which was studied as a control. Four mutations in protease (PR) were selected after 25 weeks: two flap mutations (K45R and M46I) and two novel active site mutations (T80I and P81S).
|
||
|
ACTIVE MOIETY |
Class: Aniline compound, Antiretroviral, Benzhydryl compound, Carbamate, Phosphoric acid ester, Small molecule, Sulfonamide; Mechanism of Action: HIV protease inhibitor; Highest Development Phase: Preclinical for HIV infection; Most Recent Events: 20 May 2016 PPl 100 (SC, IM) is still in preclinical development for HIV infections in Taiwan, 09 Jul 2013 No development reported - Phase-I for HIV infections in Canada (PO)
|
