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129453-61-8 molecular structure
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(1S,9R,10R,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

ChemBase ID: 823
Molecular Formular: C32H47F5O3S
Molecular Mass: 606.770796
Monoisotopic Mass: 606.31660746
SMILES and InChIs

SMILES:
S(=O)(CCCCCCCCC[C@H]1[C@H]2[C@H]3[C@](CC[C@@H]2c2c(C1)cc(O)cc2)([C@@H](O)CC3)C)CCCC(F)(F)C(F)(F)F
Canonical SMILES:
O=S(CCCC(C(F)(F)F)(F)F)CCCCCCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CC[C@@H]([C@]1(CC2)C)O
InChI:
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
InChIKey:
VWUXBMIQPBEWFH-WCCTWKNTSA-N

Cite this record

CBID:823 http://www.chembase.cn/molecule-823.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,9R,10R,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
(1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
(1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
IUPAC Traditional name
fulvestrant
(1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
(1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
Brand Name
Faslodex
Synonyms
(7a,17b)-7-[9-[(4,4,5,5,5pentafluoropentyl)Sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol
ZD 182780
ZD 9238
ZM 182780
Fulvestrant
(7α,17β)-7-[9-[4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol
ICI 182,780
fulvestrant
Fulvestrant
Faslodex
ICI 182780
CAS Number
129453-61-8
MDL Number
MFCD00903953
PubChem SID
160964286
PubChem CID
104741

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.320843  H Acceptors
H Donor LogD (pH = 5.5) 7.571834 
LogD (pH = 7.4) 7.571323  Log P 7.571841 
Molar Refractivity 155.337 cm3 Polarizability 59.35865 Å3
Polar Surface Area 57.53 Å2 Rotatable Bonds 15 
Lipinski's Rule of Five false 
Log P 6.54  LOG S -4.96 
Solubility (Water) 6.72e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
DMSO: >5 mg/mL expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
104-106°C expand Show data source
Hydrophobicity(logP)
8.9 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
KG7623000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
estrogen receptor expand Show data source
Purity
>98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C32H47F5O3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00947 external link
Item Information
Drug Groups approved; investigational
Description Fulvestrant is a drug treatment of hormone receptor-positive metastatic breast cancer in post-menopausal women with disease progression following anti-estrogen therapy. It is an estrogen receptor antagonist with no agonist effects, which works both by down-regulating and by degrading the estrogen receptor.
Indication For the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy.
Pharmacology Fulvestrant for intramuscular administration is an estrogen receptor antagonist without known agonist effects.
Toxicity There is no clinical experience with overdosage in humans.
Affected Organisms
Humans and other mammals
Biotransformation Metabolism of fulvestrant appears to involve combinations of a number of possible biotransformation pathways analogous to those of endogenous steroids, including oxidation, aromatic hydroxylation, conjugation with glucuronic acid and/or sulphate at the 2, 3 and 17 positions of the steroid nucleus, and oxidation of the side chain sulphoxide. Identified metabolites are either less active or exhibit similar activity to fulvestrant in antiestrogen models. Studies using human liver preparations and recombinant human enzymes indicate that cytochrome P-450 3A4 (CYP 3A4) is the only P-450 isoenzyme involved in the oxidation of fulvestrant; however, the relative contribution of P-450 and non-P-450 routes in vivo is unknown.
Half Life 40 days
Protein Binding 99% (mainly VLDL, LDL, and HDL)
Elimination Fulvestrant was rapidly cleared by the hepatobiliary route with excretion primarily via the feces (approximately 90%).
Renal elimination was negligible (less than 1%).
Distribution * 3 to 5 L/kg
References
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]
Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. [Pubmed]
Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1191 external link
Research Area: Breast cancer
Biological Activity:
Fulvestrant (Faslodex) is a synthetic estrogen receptor antagonist or selective estrogen receptor down-regulator (SERD). Unlike tamoxifen (which has partial agonist effects) and the aromatase inhibitors (which reduce the estrogen available to tumor cells), fulvestrant binds competitively to estrogen receptors in breast cancer cells, resulting in estrogen receptor deformation and decreased estrogen binding. In vitro studies indicate that fulvestrant reversibly inhibits the growth of tamoxifen-resistant, estrogen-sensitive, human breast cancer cell lines. [1] Fulvestrant is used for the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy. [2]
Sigma Aldrich - I4409 external link
Biochem/physiol Actions
Fulvestrant (ICI 182,780) is a selective estrogen receptor down-regulator (SERD). Fulvestrant is a high affinity estrogen receptor antagonist. IC50 = 0.29 nM. Fulvestrant is the first "pure" antiestrogen with no agonistic activity both in vitro and in vivo.
Toronto Research Chemicals - F862500 external link
A novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. Pubmed
  • • Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. Pubmed
  • • http://en.wikipedia.org/wiki/Fulvestrant
  • • Wakeling, A.E., et al.: Cancer Res., 51, 3867 (1991)
  • • Howell, A., et al.: Br. J. Cancer, 74, 300 (1991)
  • • Robertson, J.F., et al.: Cancer Res., 61, 6739 (1991)
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PATENTS

PATENTS

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INTERNET

INTERNET

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