U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry EPIMERIC
Molecular Formula C27H37N3O7S.C3H8O2
Molecular Weight 623.758
Optical Activity ( - )
Defined Stereocenters 5 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DARUNAVIR PROPYLENE GLYCOLATE

SMILES

CC(O)CO.CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@H]3OCC[C@@H]23)S(=O)(=O)C4=CC=C(N)C=C4

InChI

InChIKey=LMVMDGVDHYKETG-VBTXLZOXSA-N
InChI=1S/C27H37N3O7S.C3H8O2/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;1-3(5)2-4/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32);3-5H,2H2,1H3/t22-,23-,24+,25-,26+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C27H37N3O7S
Molecular Weight 547.664
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

Molecular Formula C3H8O2
Molecular Weight 76.0944
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Darunavir (trade name Prezista) is an orally active bis-furan-sulfonamide inhibitor of human immunodeficiency virus (HIV-1) protease. Darunavir was developed by Tibotec Pharmaceuticals (now Janssen R&D Ireland). Darunavir is indicated for the treatment of HIV-1 infection in adult and pediatric patients 3 years of age and older. The drug is co-administered with low-dose ritonavir and other anti-HIV agents. It is the only antiretroviral that has been registered at two different doses, 800/100 mg once-daily or 600/100 mg twice-daily, allowing its administration throughout the entire course of HIV disease, from naive subjects without any HIV-1 resistance to heavily treatment-experienced subjects with widespread triple-class family resistance.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.5 pM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PREZISTA

Cmax

ValueDoseCo-administeredAnalytePopulation
5272 ng/mL
800 mg 1 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
57055 ng × h/mL
800 mg 1 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens
93026 ng × h/mL
800 mg 1 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens
124698 ng × h/mL
600 mg 2 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens
126377 ng × h/mL
600 mg 2 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
800 mg 1 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens
15 h
600 mg 2 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
800 mg 1 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens
5%
600 mg 2 times / day steady-state, oral
DARUNAVIR plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Treatment-naïve adult patients and treatment-experienced adult patients with no darunavir resistance associated substitutions: 800 mg (two 400 mg tablets) taken with ritonavir 100 mg once daily and with food. Treatment-experienced adult patients with at least one darunavir resistance associated substitution: 600 mg (one 600 mg tablet) taken with ritonavir 100 mg twice daily and with food. Pediatric patients (3 to less than 18 years of age and weighing at least 10 kg): dosage of PREZISTA and ritonavir is based on body weight and should not exceed the treatmentexperienced adult dose. Do not use once daily dosing in pediatric patients. PREZISTA should be taken with ritonavir twice daily and with food.
Route of Administration: Oral
In Vitro Use Guide
Darunavir exhibits activity against laboratory strains and clinical isolates of HIV-1 and laboratory strains of HIV-2 in acutely infected T-cell lines, human peripheral blood mononuclear cells and human monocytes/macrophages with median EC50 values ranging from 1.2 to 8.5 nM (0.7 to 5.0 ng/mL). Darunavir demonstrates antiviral activity in cell culture against a broad panel of HIV-1 group M (A, B, C, D, E, F, G), and group O primary isolates with EC50 values ranging from less than 0.1 to 4.3 nM.
Substance Class Chemical
Record UNII
6M6D7F3VC7
Record Status Validated (UNII)
Record Version