CAS 129453-61-8|Fulvestrant|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,...

General Information

Structure

Molecular Formula

C₃₂H₄₇F₅O₃S

Molecular Mass

606.770796

Exact Mass

606.31660746

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

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

Polarizability

59.35865

Polar Surface Area

57.53

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

6.54

LOG S

-4.96

Solubility (Water)

6.72e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

FulvestrantfulvestrantICI 182,780FaslodexICI 182780ZD 9238ZD 182780ZM 182780Fulvestrant(7a,17b)-7-[9-[(4,4,5,5,5pentafluoropentyl)Sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol(7α,17β)-7-[9-[4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol

IUPAC name

(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 (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

IUPAC Traditional name

Brand Name

Faslodex

Names and Identifiers

Registration numbers

MDL Number

CAS Number

PubChem CID

PubChem SID

Registration numbers

Properties

Product Information

Salt Data

Free Base

Purity

>98% (HPLC)

Empirical Formula (Hill Notation)

C32H47F5O3S

Certificate of Analysis

Download link

Pharmacology Properties

Target

estrogen receptor

Safety Information

Storage Condition

-20°C

-20°C Freezer

Storage Temperature

2-8°C

MSDS Link

Download link

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

RTECS

KG7623000

German water hazard class

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00947

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

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

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.

TRC

F862500

A novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Synonyms

IUPAC name

IUPAC Traditional name

Brand Name

Faslodex

Registration numbers

MDL Number

CAS Number

PubChem CID

PubChem SID

Properties

Product Information

Salt Data

Free Base

Purity

>98% (HPLC)

Empirical Formula (Hill Notation)

C32H47F5O3S

Certificate of Analysis

Download link

Pharmacology Properties

Target

estrogen receptor

Safety Information

Storage Condition

-20°C

-20°C Freezer

Storage Temperature

2-8°C

MSDS Link

Download link

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

RTECS

KG7623000

German water hazard class

Molecule Details

DrugBank

DB00947

Drug Groups

approved; investigational

Description

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

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

• 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

Sigma Aldrich

I4409

TRC

F862500

A novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).

References

PubChem Literature

From Data Sources

• 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)

Bioactivity

PubChem BioAssay

Molecule

ID:823