017

(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE

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is present as a standalone ligand in 78 entries

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Chemical Component Summary
Name	(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE
Synonyms	Darunavir; TMC114; UIC-94017
Identifiers	[(3R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate
Formula	C₂₇ H₃₇ N₃ O₇ S
Molecular Weight	547.664
Type	NON-POLYMER
Isomeric SMILES	CC(C)C[N@@](C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)c4ccc(cc4)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

Chemical Details
Formal Charge	0
Atom Count	75
Chiral Atom Count	5
Bond Count	78
Aromatic Bond Count	12

Drug Info: DrugBank

DrugBank ID	DB01264 ?
Name	Darunavir
Groups	approved
Description	Darunavir is a protease inhibitor used with other HIV protease inhibitor drugs as well as [ritonavir] for the effective management of HIV-1 infection.[L9227] As a second-generation protease inhibitor, darunavir is designed to combat resistance to standard HIV therapy.[A2278,A2281] It was initially approved by the FDA in 2006.[L9227] 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.[A191682] Clinical trials are underway and are expected to conclude in August 2020.[L12066]
Synonyms	[(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 Darunavir propylene glycolate Darunavir Darunavir ethanolate (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 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 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N1-isobutylsulfanilamido)propyl)carbamate {(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 (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 Darunavir dihydrate Darunavirum
Brand Names	Sandoz Darunavir Apo-darunavir Mylan-darunavir Nat-darunavir Symtuza Rezolsta Mar-darunavir Darunavir 600 and 800 mg Auro-darunavir Pat-darunavir Darunavir Mylan Darunavir Krka Darunavir M-darunavir Prezcobix Prezista Darunavir Krka D.D.
Indication	Darunavir, co-administered with ritonavir, and with other antiretroviral agents, is indicated for the treatment of human immunodeficiency virus (HIV) in children age 3 or above and adults with HIV-1 infection.[L9227]
Categories	Amides Anti-HIV Agents Anti-Infective Agents Anti-Retroviral Agents Antiinfectives for Systemic Use Antiviral Agents Antivirals for Systemic Use Antivirals used in combination for the treatment of HIV infections Carbamates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Direct Acting Antivirals Enzyme Inhibitors Experimental Unapproved Treatments for COVID-19 Furans Genito Urinary System and Sex Hormones Gynecological Antiinfectives and Antiseptics HIV Protease Inhibitors Hyperglycemia-Associated Agents OATP1B1/SLCO1B1 Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates Protease Inhibitors Sulfonamides Sulfones Sulfur Compounds Viral Protease Inhibitors
ATC-Code	J05AR14 G01AE10 J05AR22 J05AR26 J05AE10
CAS number	206361-99-1

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Human immunodeficiency virus type 1 protease	PQVTLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKMIGGI...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	substrate
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor,inducer
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682