Darunavir ethanolateProduct ingredient for Darunavir

Name
Darunavir ethanolate
Drug Entry
Darunavir

Darunavir is a protease inhibitor used with other HIV protease inhibitor drugs as well as ritonavir for the effective management of HIV-1 infection.17 As a second-generation protease inhibitor, darunavir is designed to combat resistance to standard HIV therapy.2,5 It was initially approved by the FDA in 2006.17

Darunavir is being studied as a possible treatment for SARS-CoV-2, the coronavirus responsible for COVID-19, due to in vitro evidence supporting its ability to combat this infection.14 Clinical trials are underway and are expected to conclude in August 2020.19

Accession Number
DBSALT001338
Structure
Thumb
Synonyms
Darunavir ethnolate
UNII
33O78XF0BW
CAS Number
635728-49-3
Weight
Average: 593.74
Monoisotopic: 593.277086531
Chemical Formula
C29H43N3O8S
InChI Key
QWSHKNICRJHQCY-VBTXLZOXSA-N
InChI
InChI=1S/C27H37N3O7S.C2H6O/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26;1-2-3/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32);3H,2H2,1H3/t22-,23-,24+,25-,26+;/m0./s1
IUPAC Name
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate; ethanol
SMILES
CCO.[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1
ChemSpider
21230319
ChEMBL
CHEMBL1201127
Predicted Properties
PropertyValueSource
Water Solubility0.0668 mg/mLALOGPS
logP1.76ALOGPS
logP2.82ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.59ChemAxon
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area140.42 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142.34 m3·mol-1ChemAxon
Polarizability57.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon