2-Propenoic acid, 4-phenoxybutyl ester (CHEM009097)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:58:06 UTC
Update Date2016-11-09 01:13:55 UTC
Accession NumberCHEM009097
Identification
Common Name2-Propenoic acid, 4-phenoxybutyl ester
ClassSmall Molecule
DescriptionAnastrozole is a non-steroidal aromatase inhibitor (AI), similar to , used to decrease circulating estrogen levels in the treatment of postmenopausal women with estrogen-responsive breast cancer. Anastrozole is also related to , a steroidal AI, but its non-steroidal nature provides stark advantages including a lack of steroid-associated adverse effects such as weight gain and acne. Aromatase inhibitors, including anastrozole, have become endocrine drugs of choice in the treatment of postmenopausal breast cancer due to a more favourable efficacy and adverse effect profile as compared to earlier estrogen receptor modulators such as . Anastrozole was first approved for use in the United States in 1995.
Contaminant Sources
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ArimidexKegg
alpha,alpha,Alpha',alpha'-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-m-benzenediacetonitrileHMDB
AnastrozolHMDB
a,a,Alpha',alpha'-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-m-benzenediacetonitrileHMDB
Α,α,alpha',alpha'-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-m-benzenediacetonitrileHMDB
AstraZeneca brand OF anastrozoleHMDB
ICI D1033HMDB
Zeneca brand OF anastrozoleHMDB
Zeneca ZD 1033HMDB
2,2'-(5-(1H-1,2,4-Triazol-1-ylmethyl)-1,3-phenylene)bis(2-methylpropionitrile)HMDB
Astra brand OF anastrozoleHMDB
AnastrazoleHMDB
Chemical FormulaC17H19N5
Average Molecular Mass293.366 g/mol
Monoisotopic Mass293.164 g/mol
CAS Registry Number103969-85-3
IUPAC Name2-[3-(1-cyano-1-methylethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
Traditional Nameanastrozole
SMILESCC(C)(C#N)C1=CC(=CC(CN2C=NC=N2)=C1)C(C)(C)C#N
InChI IdentifierInChI=1S/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3
InChI KeyYBBLVLTVTVSKRW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.066 g/LALOGPS
logP2.31ALOGPS
logP3.03ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.47 m³·mol⁻¹ChemAxon
Polarizability31.97 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3290000000-ff4ef0855ebb4330d2d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004l-1390000000-8636c0aef7d79b805328Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004l-1390000000-8636c0aef7d79b805328Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004l-0190000000-739ac0c546bb150b1c60Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0090000000-8ccdc5fa9f18334eae92Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0970000000-631de023e85e74dc9b97Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-0090000000-da446dd012935939477aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-004i-0290000000-68b444c53777d3d51749Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00kf-0910000000-40a907f3bc5fa1999ffdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00e9-0900000000-55004c246dccb53413bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0980000000-71cd7bb463fca110eeabSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-0290000000-2b885de3e2d4dc88aa81Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00e9-0900000000-5113a05488a50bd3517cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-01b9-0900000000-908023356faf6f180af3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-84795d1e4c8cdc8517aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-6a08f214a3b45616d2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-2390000000-cad4b3339fe0a358312eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-84795d1e4c8cdc8517aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-6a08f214a3b45616d2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-2390000000-cad4b3339fe0a358312eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-84795d1e4c8cdc8517aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-6a08f214a3b45616d2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-2390000000-cad4b3339fe0a358312eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-cca188a9698d9ce00e77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-7e154d941cb439c9f5a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5290000000-bd403a6901863274c5b7Spectrum
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 IDDB01217
HMDB IDHMDB0015348
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAnastrozole
Chemspider ID2102
ChEBI ID2704
PubChem Compound ID2187
Kegg Compound IDC08159
YMDB IDYMDB15939
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2.
2. Nabholtz JM: Role of anastrozole across the breast cancer continuum: from advanced to early disease and prevention. Oncology. 2006;70(1):1-12. Epub 2006 Jan 26.
3. Santen RJ, Brodie H, Simpson ER, Siiteri PK, Brodie A: History of aromatase: saga of an important biological mediator and therapeutic target. Endocr Rev. 2009 Jun;30(4):343-75. doi: 10.1210/er.2008-0016. Epub 2009 Apr 23.
4. Mauras N, Bishop K, Merinbaum D, Emeribe U, Agbo F, Lowe E: Pharmacokinetics and pharmacodynamics of anastrozole in pubertal boys with recent-onset gynecomastia. J Clin Endocrinol Metab. 2009 Aug;94(8):2975-8. doi: 10.1210/jc.2008-2527. Epub 2009 May 26.
5. Gangadhara S, Bertelli G: Long-term efficacy and safety of anastrozole for adjuvant treatment of early breast cancer in postmenopausal women. Ther Clin Risk Manag. 2009 Aug;5(4):291-300. Epub 2009 May 4.
6. Milani M, Jha G, Potter DA: Anastrozole Use in Early Stage Breast Cancer of Post-Menopausal Women. Clin Med Ther. 2009 Mar 31;1:141-156.