2R9

N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-[(7-chloro-4-methoxyisoquinolin-1-yl)oxy]-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}-L-prolinamide

Created:	2014-01-10
Last modified:	2021-03-01

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4 entries where 2R9 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	97
Chiral Atom Count	5
Bond Count	101
Aromatic Bond Count	11

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Chemical Component Summary
Name	N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-[(7-chloro-4-methoxyisoquinolin-1-yl)oxy]-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}-L-prolinamide
Synonyms	Asunaprevir
Systematic Name (OpenEye OEToolkits)	tert-butyl N-[(2S)-1-[(2S,4R)-4-(7-chloranyl-4-methoxy-isoquinolin-1-yl)oxy-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenyl-cyclopropyl]carbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxidanylidene-butan-2-yl]carbamate
Formula	C₃₅ H₄₆ Cl N₅ O₉ S
Molecular Weight	748.286
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(N5C(C(=O)NC2(C(=O)NS(=O)(=O)C1CC1)CC2/C=C)CC(Oc3ncc(OC)c4c3cc(Cl)cc4)C5)C(NC(=O)OC(C)(C)C)C(C)(C)C
SMILES	CACTVS	3.385	COc1cnc(O[CH]2C[CH](N(C2)C(=O)[CH](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)N[C]3(C[CH]3C=C)C(=O)N[S](=O)(=O)C4CC4)c5cc(Cl)ccc15
SMILES	OpenEye OEToolkits	1.7.6	CC(C)(C)C(C(=O)N1CC(CC1C(=O)NC2(CC2C=C)C(=O)NS(=O)(=O)C3CC3)Oc4c5cc(ccc5c(cn4)OC)Cl)NC(=O)OC(C)(C)C
Canonical SMILES	CACTVS	3.385	COc1cnc(O[C@@H]2C[C@H](N(C2)C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)N[C@@]3(C[C@H]3C=C)C(=O)N[S](=O)(=O)C4CC4)c5cc(Cl)ccc15
Canonical SMILES	OpenEye OEToolkits	1.7.6	CC(C)(C)[C@@H](C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@@]2(C[C@H]2C=C)C(=O)NS(=O)(=O)C3CC3)Oc4c5cc(ccc5c(cn4)OC)Cl)NC(=O)OC(C)(C)C
InChI	InChI	1.03	InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
InChIKey	InChI	1.03	XRWSZZJLZRKHHD-WVWIJVSJSA-N

Drug Info: DrugBank

DrugBank ID	DB11586
Name	Asunaprevir
Groups	withdrawn approved investigational
Description	Asunaprevir, also named BMS-650032, is a potent hepatitis C virus (HCV) NS3 protease inhibitor. It has been shown to have a very high efficacy in dual-combination regimens with daclatasvir in patients chronically infected with HCV genotype 1b.[A32528] It was developed by Bristol-Myers Squibb Canada and approved by Health Canada on April 22, 2016. The commercialization of asunaprevir was cancelled one year later on October 16, 2017.[L1113]
Synonyms	Asunaprevir
Brand Names	Asunaprevir Sunvepra
Indication	Asunaprevir is indicated in combination with other agents for the treatment of chronic hepatitis C in adult patients with hepatitis C virus genotypes 1 or 4 and compensated liver cirrhosis.[L2278] Hepatitis C is a liver disease caused by the hepatitis C virus. The chronic state of this condition accounts for 60-80% of the cases from which the risk of cirrhosis of the liver within 20 years is of around 15-30%.[L2281] The genotype 1 is the most common type of hepatitis C in the United States and the most difficult to treat.[L2282]
Categories	Amides Antiinfectives for Systemic Use Antiviral Agents Antivirals for Systemic Use Antivirals for treatment of HCV infections Cytochrome P-450 CYP2A6 Substrates Cytochrome P-450 CYP2B6 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inducers Cytochrome P-450 CYP3A4 Inducers (weak) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Inducers Cytochrome P-450 CYP3A5 Inducers (weak) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Direct Acting Antivirals Enzyme Inhibitors HCV Protease Inhibitors Heterocyclic Compounds, Fused-Ring HIV Protease Inhibitors OATP1B1/SLCO1B1 Inhibitors OATP1B1/SLCO1B1 Substrates OATP1B3 inhibitors OATP2B1/SLCO2B1 substrates Organic Anion Transporting Polypeptide 2B1 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates Protease Inhibitors Sulfones Sulfur Compounds
ATC-Code	J05AP06 J05AP58
CAS number	630420-16-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Genome polyprotein	MSTNPKPQRKTKRNTNRRPQDVKFPGGGQIVGGVYLLPRRGPRLGVRAPR...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inducer
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate,inducer
Cytochrome P450 2A6	MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...	unknown	substrate
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	inhibitor
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
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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