Darunavir (CHEM019245)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:56:42 UTC
Update Date2016-11-09 01:15:57 UTC
Accession NumberCHEM019245
Identification
Common NameDarunavir
ClassSmall Molecule
DescriptionDarunavir is a protease inhibitor used with other HIV protease inhibitor drugs as well as for the effective management of HIV-1 infection. As a second-generation protease inhibitor, darunavir is designed to combat resistance to standard HIV therapy. It was initially approved by the FDA in 2006. With the recent SARS-CoV-2 outbreak of 2019 that causes coronavirus disease, darunavir is being studied as a possible treatment for SARS-CoV-2 due to in vitro evidence supporting its ability to combat this infection. Clinical trials are underway and are expected to conclude in August 2020.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamateChEBI
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamATEChEBI
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamateChEBI
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamateChEBI
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterChEBI
DarunavirumChEBI
N-((1S,2R)-3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamideChEBI
TMC114ChEBI
{(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterChEBI
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamic acidGenerator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulphanilamido)propyl)carbamateGenerator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulphanilamido)propyl)carbamic acidGenerator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamic acidGenerator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulphonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamateGenerator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulphonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamic acidGenerator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acidGenerator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamateGenerator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acidGenerator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acidGenerator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamateGenerator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acidGenerator
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterGenerator
[(S)-3-[(4-Amino-benzenesulphonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterGenerator
[(S)-3-[(4-Amino-benzenesulphonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterGenerator
N-((1S,2R)-3-(((4-Aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamideGenerator
{(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterGenerator
{(1S,2R)-3-[(4-amino-benzenesulphonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterGenerator
{(1S,2R)-3-[(4-amino-benzenesulphonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) esterGenerator
AIDS073035HMDB
TMC-114HMDB
UIC-94017HMDB
114, TMCHMDB
TMC 114HMDB
Ethanolate, darunavirHMDB
Darunavir ethanolateHMDB
PrezistaHMDB
Chemical FormulaC27H37N3O7S
Average Molecular Mass547.664 g/mol
Monoisotopic Mass547.235 g/mol
CAS Registry Number206361-99-1
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
Traditional Namedarunavir
SMILES[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
InChI IdentifierInChI=1S/C27H37N3O7S/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/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
InChI KeyCJBJHOAVZSMMDJ-HEXNFIEUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Phenylbutylamine
  • Amphetamine or derivatives
  • Benzenesulfonyl group
  • Furofuran
  • Aniline or substituted anilines
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Tetrahydrofuran
  • Carbamic acid ester
  • Aminosulfonyl compound
  • Secondary alcohol
  • Carbonic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142.34 m³·mol⁻¹ChemAxon
Polarizability57.24 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7395120000-9ee6643d8e957bfc6883Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-08i3-8659131000-a5895dfe8fa0c5374f22Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Darunavir,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aor-0900800000-e427a102e3a7551cc732Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-8ab8c2b3421f4a277282Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-2900000000-eddacc917eaf16abe9d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-2900000000-86c785caeafe3b4a10c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4l-5900000000-69bc90a59383cb5a804bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4l-8900000000-f481d0932a99692c87d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0900000000-40373637b670c5395ffdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0aor-0900800000-f59913cdbcd62042530aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-2900000000-10dadadeebe1e6ec0164Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000g-0009760000-f730e27547a482694ebcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0009000000-fcd18a6f4e9084f0f8f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0469000000-716a2ae87ad9df6765fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0941000000-5e0dbe51025009642b33Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0910000000-2411514d55bfa3c4e81fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-2309000000-e6767f5d8648334c41c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9621000000-3a7c794f5e3f473b9ad5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9400000000-16b363cdd836532460ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-2900000000-98bfa9c688e4cb2dbbc3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4l-4900000000-05c5a10ff111a5d1c9bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-6900000000-f59c1c0d97f0a8ab00d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-8e1cc4b8ca6f49bcfe56Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000g-0009760000-26cdc56a39511d44e965Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0006-2309000000-b56fe3acae7c21ddaba0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0941000000-5e0dbe51025009642b33Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0469000000-c470e3e505d43b7089afSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01264
HMDB IDHMDB0015393
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB ID017
Wikipedia LinkDarunavir
Chemspider ID184733
ChEBI ID367163
PubChem Compound ID213039
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. De Meyer S, Azijn H, Surleraux D, Jochmans D, Tahri A, Pauwels R, Wigerinck P, de Bethune MP: TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. Antimicrob Agents Chemother. 2005 Jun;49(6):2314-21.
2. Kovalevsky AY, Tie Y, Liu F, Boross PI, Wang YF, Leshchenko S, Ghosh AK, Harrison RW, Weber IT: Effectiveness of nonpeptide clinical inhibitor TMC-114 on HIV-1 protease with highly drug resistant mutations D30N, I50V, and L90M. J Med Chem. 2006 Feb 23;49(4):1379-87.
3. Koh Y, Matsumi S, Das D, Amano M, Davis DA, Li J, Leschenko S, Baldridge A, Shioda T, Yarchoan R, Ghosh AK, Mitsuya H: Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization. J Biol Chem. 2007 Sep 28;282(39):28709-20. Epub 2007 Jul 17.
4. Back D, Sekar V, Hoetelmans RM: Darunavir: pharmacokinetics and drug interactions. Antivir Ther. 2008;13(1):1-13.
5. Tremblay CL: Combating HIV resistance - focus on darunavir. Ther Clin Risk Manag. 2008 Aug;4(4):759-66.
6. Company Website: http://www.prezista.com/prezista/qanda_about_prezista.html
7. Medilexicon: http://www.medilexicon.com/drugs/prezista.php
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15771427
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16480273
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682