Drug Information

General Information
Drug ID
DR00514
Drug Name
Darunavir
Synonyms
(3-((4-aminobenzenesulfonyl)isobutylamino)-1-benzyl-2-hydroxypropyl)carbamic acid hexahydrofuro(2,3-b)furan-3-yl ester; (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE; (3R,3aS,6aR)-Hexahydrofuro(2,3-b)furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N1-isobutylsulfanilamido)propyl)carbamate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate; (3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate; (3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate; AIDS073035; Carbamic acid, [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester; Darunavir (USAN/INN); Darunavir [USAN]; Darunavirum; Darunavirum [INN-Latin]; 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)carboxamide; Prezista; Prezista(TM); TMC 114; TMC-114; TMC114; UIC 94017; UIC-94017; UIC-96017; [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate; [(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) ester; {(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) ester
Drug Type
Small molecular drug
Indication Human immunodeficiency virus infection [ICD11:1C62.Z] Approved [1]
Therapeutic Class
Antiviral Agents
Structure
3D MOL 2D MOL
Formula
C27H37N3O7S
Canonical SMILES
CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
InChI
InChI=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
InChIKey
CJBJHOAVZSMMDJ-HEXNFIEUSA-N
CAS Number
CAS 206361-99-1
Pharmaceutical Properties Molecular Weight 547.7 Topological Polar Surface Area 149
Heavy Atom Count 38 Rotatable Bond Count 12
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
XLogP
2.9
PubChem CID
213039
PubChem SID
10322685 ,10322696 ,104223585 ,104234207 ,11108879 ,113453152 ,115001517 ,117695824 ,12015589 ,14719987 ,14719990 ,14720157 ,14788134 ,17397753 ,30417278 ,46394098 ,46394099 ,46394100 ,46394252 ,46394253 ,46394275 ,46394276 ,46506908 ,49661683 ,49743126 ,49743141 ,49743143 ,50070565 ,50071308 ,50074527 ,50113275 ,50333303 ,53777066 ,57399654 ,628316 ,7884953 ,85098698 ,85177032 ,85177058 ,85756739 ,85756740 ,87351130 ,87557585 ,87557699 ,87557709 ,87557710 ,9371109 ,99226867 ,99226870 ,99226871
ChEBI ID
CHEBI:367163
TTD Drug ID
D03IGH
DT(s) Transporting This Drug OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [2]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [3]
P-GP Transporter Info P-glycoprotein 1 Substrate [4]
References
1 Darunavir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 P-glycoprotein mediates efflux transport of darunavir in human intestinal Caco-2 and ABCB1 gene-transfected renal LLC-PK1 cell lines. Biol Pharm Bull. 2009 Sep;32(9):1588-93.
3 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
4 Impact of drug transporters on cellular resistance towards saquinavir and darunavir. J Antimicrob Chemother. 2010 Nov;65(11):2319-28.

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