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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015082
Secondary Accession Numbers
  • HMDB15082
Metabolite Identification
Common NameFulvestrant
DescriptionFulvestrant, also known as ici 182,780 or faslodex, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Fulvestrant is an extremely weak basic (essentially neutral) compound (based on its pKa). Fulvestrant is a potentially toxic compound.
Structure
Data?1582753256
Synonyms
ValueSource
ICI 182,780HMDB
(1S,9R,11S,14S,15S)-15-Methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulphinyl)nonyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diolHMDB
FaslodexHMDB
7-(9-(4,4,5,5,5-Pentafluoropentylsulfinyl)nonyl)estra-1,3,5(10)-triene-3,17-diolHMDB
Chemical FormulaC32H47F5O3S
Average Molecular Weight606.771
Monoisotopic Molecular Weight606.316607085
IUPAC Name(1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol
Traditional Namefaslodex(ici 182,780)
CAS Registry Number129453-61-8
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])C2[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=CC(O)=CC=C12
InChI Identifier
InChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-,27+,28+,29?,30+,41?/m1/s1
InChI KeyVWUXBMIQPBEWFH-LQKBAPIOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Sulfoxide
  • Secondary alcohol
  • Sulfinyl compound
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Organosulfur compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0067 g/LNot Available
LogP8.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
logP6.54ALOGPS
logP7.57ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity155.34 m³·mol⁻¹ChemAxon
Polarizability65.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-269.69130932474
DeepCCS[M+Na]+245.10930932474
AllCCS[M+H]+234.532859911
AllCCS[M+H-H2O]+233.832859911
AllCCS[M+NH4]+235.132859911
AllCCS[M+Na]+235.332859911
AllCCS[M-H]-222.532859911
AllCCS[M+Na-2H]-226.132859911
AllCCS[M+HCOO]-230.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fulvestrant[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])C2[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=CC(O)=CC=C123306.9Standard polar33892256
Fulvestrant[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])C2[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=CC(O)=CC=C124434.3Standard non polar33892256
Fulvestrant[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])C2[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=CC(O)=CC=C124097.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fulvestrant,1TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O)C=C4C[C@@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)C3[C@@H]1CC[C@@H]2O[Si](C)(C)C3869.8Semi standard non polar33892256
Fulvestrant,1TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4C[C@@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)C3[C@@H]1CC[C@@H]2O3896.6Semi standard non polar33892256
Fulvestrant,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4C[C@@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)C3[C@@H]1CC[C@@H]2O[Si](C)(C)C3892.1Semi standard non polar33892256
Fulvestrant,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2C3[C@H](CC[C@]12C)C1=CC=C(O)C=C1C[C@H]3CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F4101.9Semi standard non polar33892256
Fulvestrant,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C[C@@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)C1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]124135.9Semi standard non polar33892256
Fulvestrant,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C[C@@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)C1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]124363.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (Non-derivatized) - 70eV, Positivesplash10-08or-1435190000-ac0a296ce776ab03ad072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5517759000-8aeb8c895093525bd51b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fulvestrant GC-MS ("Fulvestrant,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 10V, Positive-QTOFsplash10-052r-0132295000-ef5f5c93e013c704e8b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 20V, Positive-QTOFsplash10-08fr-0749421000-c147033104043b9655672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 40V, Positive-QTOFsplash10-03di-0924010000-bb9bcf231b1241b2903f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 10V, Negative-QTOFsplash10-0a4i-0540649000-e293a1b739ec6e71041c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 20V, Negative-QTOFsplash10-052b-4361911000-637e5739391e190c55e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 40V, Negative-QTOFsplash10-0002-9522300000-e3377ef73b716caff9942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 10V, Positive-QTOFsplash10-0a4i-0000039000-71d23dc80a26491f74452021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 20V, Positive-QTOFsplash10-003i-1020971000-f59364a4fd57cbcdc4332021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 40V, Positive-QTOFsplash10-0005-3361910000-57f1e34f3ddf874acecc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 10V, Negative-QTOFsplash10-0a4i-0000009000-f4c3786f528a595792042021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 20V, Negative-QTOFsplash10-0a4j-0000915000-1073e187bdb2ba6a68c82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fulvestrant 40V, Negative-QTOFsplash10-004j-1104901000-00561480fc85161becf62021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00947 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00947 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00947
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21475029
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFulvestrant
METLIN IDNot Available
PubChem Compound17756771
PDB IDNot Available
ChEBI ID31638
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. doi: 10.1517/14656561003641982. [PubMed:20151846 ]
  2. Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. [PubMed:12490735 ]
  3. Kansra S, Yamagata S, Sneade L, Foster L, Ben-Jonathan N: Differential effects of estrogen receptor antagonists on pituitary lactotroph proliferation and prolactin release. Mol Cell Endocrinol. 2005 Jul 15;239(1-2):27-36. [PubMed:15950373 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4
References
  1. Curran M, Wiseman L: Fulvestrant. Drugs. 2001;61(6):807-13; discussion 814. [PubMed:11398912 ]
  2. Elkak AE, Mokbel K: Pure antiestrogens and breast cancer. Curr Med Res Opin. 2001;17(4):282-9. [PubMed:11922402 ]
  3. Dow KH: Existing and emerging endocrine therapies for breast cancer. Cancer Nurs. 2002 Apr;25 Suppl 2:6S-11S. [PubMed:12080538 ]
  4. Bundred N, Howell A: Fulvestrant (Faslodex): current status in the therapy of breast cancer. Expert Rev Anticancer Ther. 2002 Apr;2(2):151-60. [PubMed:12113237 ]
  5. Morris C, Wakeling A: Fulvestrant ('Faslodex')--a new treatment option for patients progressing on prior endocrine therapy. Endocr Relat Cancer. 2002 Dec;9(4):267-76. [PubMed:12542403 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. doi: 10.1517/14656561003641982. [PubMed:20151846 ]
  8. McKeage K, Curran MP, Plosker GL: Fulvestrant: a review of its use in hormone receptor-positive metastatic breast cancer in postmenopausal women with disease progression following antiestrogen therapy. Drugs. 2004;64(6):633-48. [PubMed:15018596 ]
  9. Jones SE, Pippen J: Effectiveness and tolerability of fulvestrant in postmenopausal women with hormone receptor-positive breast cancer. Clin Breast Cancer. 2005 Apr;6 Suppl 1:S9-14. [PubMed:15865850 ]