BOIS DE ROSE, OIL (ANIBA ROSAEODORA DUCKE) (CHEM004857)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:55:38 UTC
Update Date2016-11-09 01:09:26 UTC
Accession NumberCHEM004857
Identification
Common NameBOIS DE ROSE, OIL (ANIBA ROSAEODORA DUCKE)
ClassSmall Molecule
DescriptionTelaprevir is a direct acting antiviral medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients . Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as Telaprevir. Telaprevir is an inhibitor of NS3/4A, a serine protease enzyme, encoded by HCV genotype 1 . These enzymes are essential for viral replication and serve to cleave the virally encoded polyprotein into mature proteins like NS4A, NS4B, NS5A and NS5B. The barrier for develoment of resistance to NS3/4A inhibitors is lower than that of NS5B inhibitors, another class of DAAs . Subtitutions at amino acid positions 155, 156, or 168 are known to confer resistance. The substitutions of the enzyme's catalytic triad consisting of H58, D82, and S139 are also likely to alter the affinity of the drug for NS3/4A or the activity of the enzyme itself. Despite this disadvantage Telaprevir is still effective against HCV when paired with , , and . Telaprevir, , , and were used with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of daily administration of the combination therapy followed by 12 or 36 weeks of therapy with , , and . SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality . Telaprevir was available as a fixed dose product (tradename Incivek) used for the treatment of chronic Hepatitis C. Approved in May 2011 by the FDA, Telaprevir was indicated for the treatment of HCV genotype 1 in combination with , , and . Telaprevir has since been withdrawn from the market.
Contaminant Sources
  • EAFUS Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,3AR,6as)-(2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydrocyclopenta(c)pyrrole-1-carboxamideChEBI
IncivekChEBI
VX 950ChEBI
VX-950ChEBI
IncivoKegg
AIDS-213006HMDB
AIDS213006HMDB
LY-570310HMDB
MP-424HMDB
VRT111950HMDB
VX950 CPDHMDB
Chemical FormulaC36H53N7O6
Average Molecular Mass679.849 g/mol
Monoisotopic Mass679.406 g/mol
CAS Registry Number8015-77-8
IUPAC Name(3S)-3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide
Traditional Nameincivek
SMILES[H][C@@]12CCC[C@]1([H])[C@H](N(C2)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)C1=NC=CN=C1)C1CCCCC1)C(C)(C)C)C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1
InChI IdentifierInChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
InChI KeyBBAWEDCPNXPBQM-GDEBMMAJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyrazine carboxylic acid or derivatives
  • Pyrazinecarboxamide
  • 2-heteroaryl carboxamide
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Pyrazine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • 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 Solubility0.036 g/LALOGPS
logP2.56ALOGPS
logP2.58ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.86ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area179.56 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity180.04 m³·mol⁻¹ChemAxon
Polarizability74.37 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-0159-9223442000-e5383967958c67d6112bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-6843629000-79c7b7ded030cb60adc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9552200000-560c5847843df7fb12eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yi-9741000000-d0cce25ee4a591dc4942Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3110139000-1e704c91c3d845bfeca5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9122233000-56280db5fa8fe46604b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9221000000-b4c08449c2485eb5aaa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0422819000-25e8b17badb7c49ff195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3693102000-b3e1a171d8cc901ea4ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-7920000000-e6576b8ab01ad0ece8b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1122029000-dfbe8fa31727dcf49f1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-6292000000-2e22a254a5f3a2d0c866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004u-9310210000-13381e48447867199139Spectrum
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 IDDB05521
HMDB IDHMDB0015616
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTelaprevir
Chemspider ID2279948
ChEBI ID68595
PubChem Compound ID3010818
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Znabet A, Polak MM, Janssen E, de Kanter FJ, Turner NJ, Orru RV, Ruijter E. A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions. Chem Commun (Camb). 2010 Nov 14;46(42):7918-20. Epub 2010 Sep 20.
2. Liu-Young G, Kozal MJ: Hepatitis C protease and polymerase inhibitors in development. AIDS Patient Care STDS. 2008 Jun;22(6):449-57. doi: 10.1089/apc.2007.0199.
3. Kim JJ, Culley CM, Mohammad RA: Telaprevir: an oral protease inhibitor for hepatitis C virus infection. Am J Health Syst Pharm. 2012 Jan 1;69(1):19-33. doi: 10.2146/ajhp110123.
4. Forestier N, Zeuzem S: Telaprevir for the treatment of hepatitis C. Expert Opin Pharmacother. 2012 Mar;13(4):593-606. doi: 10.1517/14656566.2012.660524. Epub 2012 Feb 15.
5. Garg V, Kauffman RS, Beaumont M, van Heeswijk RP: Telaprevir: pharmacokinetics and drug interactions. Antivir Ther. 2012;17(7):1211-21. doi: 10.3851/IMP2356. Epub 2012 Sep 7.
6. Authors unspecified: Telaprevir. Drugs R D. 2010;10(3):179-202. doi: 10.2165/11586020-000000000-00000.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20945948
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21884670
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21940388
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22039291
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22095516
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22169996
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22180548
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212567
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22222799
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22239508
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22345334
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22383557
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22404758
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22423262
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22439668
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22471376
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22506260
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22511937
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22515133
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=22537438
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=22642697
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=22806681
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=22889114
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=22902721
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=22954756
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=23016967
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682