ChemicalBook > Product Catalog >API >Antineoplastic agents >Hormonal antineoplastic drugs >Fulvestrant

Fulvestrant

Fulvestrant, sold under the trade name Faslodex among others, is used to treat hormone receptor positive breast cancer (breast cancer that depends on hormones such as estrogen to grow) in women who have experienced menopause (change of life; end of monthly menstrual periods) and whose breast cancer has worsened after they were treated with antiestrogen medications such as tamoxifen (Nolvadex). It works to treat hormone receptor (HR)-positive metastatic breast cancer in postmenopausal women with disease progression as well as HR-positive, HER2-negative advanced breast cancer in combination with palbociclib in women with disease progression after endocrine therapy. It is given by injection into a muscle.
Fulvestrant Suppliers list
Company Name: Xi'an Yutbon Pharmaceutical Technology Co., Ltd
Tel: 029-81140587 +8618717328141
Email: sales@yutbon.com
Products Intro: Product Name:Fulvestrant
CAS:129453-61-8
Purity:99% Package:500g,1kg,10kg,100kg Remarks:Factory stock, quality assurance, price concessions
Company Name: Shaoxing Fangxiao Chemical Co., LTD
Tel: +86-13456999252 +86-13868192239
Email: kenny@fangxiaochem.com
Products Intro: Product Name:Fulvestrant
Purity:99.0% Package:1Kg/Bag;0USD
Company Name: AFINE CHEMICALS LIMITED
Tel: 0571-85134551
Email: info@afinechem.com
Products Intro: Product Name:Fulvestrant
CAS:129453-61-8
Purity:98%+ Package:Standard or custom package Remarks:excellent quality and reliable supplier
Company Name: Capot Chemical Co.,Ltd.
Tel: 571-85586718 +8613336195806
Email: sales@capotchem.com
Products Intro: Product Name:Fulvestrant
CAS:129453-61-8
Purity:98%(Min,HPLC) Package:100g;1kg;5kg,10kg,25kg,50kg
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: +86-0371-55170693 +86-19937530512
Email: info@tianfuchem.com
Products Intro: Product Name:Fulvestrant 129453-61-8
CAS:129453-61-8
Purity:99% Package:25KG;5KG;1KG

Fulvestrant manufacturers

  • Fulvestrant
  • $0.00 / 1g
  • 2022-11-05
  • CAS:129453-61-8
  • Min. Order: 1g
  • Purity: 99.9%
  • Supply Ability: 200kgs
  • Fulvestrant
  • $0.00 / 1KG
  • 2022-02-25
  • CAS:129453-61-8
  • Min. Order: 100g
  • Purity: 98%+
  • Supply Ability: 100kg
  • Fulvestrant
  • $200.00 / 1g
  • 2022-02-21
  • CAS:129453-61-8
  • Min. Order: 1g
  • Purity: 99.99%
  • Supply Ability: 20 tons

Related articles

Fulvestrant Basic information
Indications and Usage Mechanisms of Action Pharmacokinetics Adverse reactions
Product Name:Fulvestrant
Synonyms:zd182780;zm182780;(1S,9R,10R,11S,14S,15S)-15-Methyl-9-{9-[(R)-(4,4,5,5,5-pentafluoropentane)sulfinyl]nonyl}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol;Fulvestrant Estra-1,3,5(10)-triene-3,17-diol, 7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-, (7 ,17 )-;Fulvestrant (Faslodex);ZD 9238;Fulvestrant(ICI 182,780);(717b)- 7-[9-[4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol
CAS:129453-61-8
MF:C32H47F5O3S
MW:606.77
EINECS:642-998-6
Product Categories:Nuclear Receptors;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Sulfur & Selenium Compounds;FASLODEX;Anti-cancer&immunity;Inhibitors
Mol File:129453-61-8.mol
Fulvestrant Structure
Fulvestrant Chemical Properties
Melting point 104-106°C
Boiling point 674.8±55.0 °C(Predicted)
density 1.201±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >5mg/mL
form powder
pka10.27±0.70(Predicted)
color White
Stability:Stable for 2 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChIKeyVWUXBMIQPBEWFH-WCCTWKNTSA-N
CAS DataBase Reference129453-61-8(CAS DataBase Reference)
Safety Information
WGK Germany 3
RTECS KG7623000
HS Code 2937230000
Hazardous Substances Data129453-61-8(Hazardous Substances Data)
MSDS Information
Fulvestrant Usage And Synthesis
Indications and UsageFulvestrant is a muscle injection drug developed by the company AstraZeneca and is suitable for treating postmenopausal women with estrogen receptor-positive metastasized breast cancer whose condition continued to worsen despite antiestrogen treatment. Fulvestrant is the only antiestrogen drug that can be widely clinically used following unsuccessful tamoxifen treatment. This drug is a type of endocrine therapy, so it will not cause any adverse effects commonly seen in chemotherapy, giving it relatively good patient compliance. Multiple clinical trials have found that 250mg Fulvestrant is effective and consistently safe as a second line of treatment for advanced breast cancer.
Mechanisms of ActionMany breast cancer cells contain estrogen receptors (ER), so estrogen stimulates breast cancer growth. Fulvestrant is a steroid estrogen receptor antagonist, and its chemical structure is similar to estradiol, except that its 7α position contains a linking group. Fulvestrant is a 17β-estradiol alkylamine analogue, and it binds with, prevents, and decreases ER to inhibit the estrogen signal transduction pathway. It binds competitively with ER, has a similar affinity with ER as estrogen, and inhibits gene activation stimulated by estrogen, thus affecting necessary estrogen-related processes in cell circulation. Its fulvastans have a similar affinity with ER as estrogen and is 100 times that of tamoxifen.
PharmacokineticsFulvestrant has a relatively poor oral bioavailability, so it is commonly injected into the muscle with lipids as excipients. In an open, random and multicenter study on postmenopausal women with advanced breast cancer, one 5ml or 2 2.5ml dosages containing 250mg were injected, and their pharmacokinetics and poisonous side effects did not differ greatly, while its blood concentration was dose-dependent and had individual differences. In the 7-day treatment period, serum LH, FSH or SBHG levels did not change significantly. This drug does not pass through the blood-brain barrier and will not cause side effects such as vasomotor symptoms.
Adverse reactionsFulvestrant causes relatively fewer side effects, including brief vaginal bleeding, body odor change, and sleepwalking. There have not been any reports of effects such as vaginal dryness, weight gain, blood clotting abnormalities, thrombus formation and libido change, and characteristics such as facial flushing and sweating are not affected. A small-scale stage III clinical trial on 19 women with metastasized breast cancer who used this drug showed that its clinical efficacy was 67% and there were no serious safety issues. It showed that continuous monthly injections were crucial and that it was well-tolerated, with only slight swelling and paint at injection site, while facial flushing, uterine lining thickness, sex hormone binding globulin levels, follicle stimulating hormones levels, and luteinizing hormone levels all showed no change.
DescriptionFulvestrant was launched in the US as a novel once monthly injectable steroidal estrogen antagonist for the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following estrogen therapy. This 7a-alkylsulphinyl derivative of estradiol can be prepared in 10 steps from 6,7- didehydro-19-nor-testosterone by successive conjugate addition of the organocuprate derived from O-protected 9-bromononan-l-o1 followed by aromatization of the resulting enone, then activation of the protected primary alcohol, substitution with 4,4,5,5,5- pentafluoropentanthiol and oxidation to the sulfoxide. Fulvestrant is the first “pure” estrogen antagonist from a novel class known as selective estrogen receptor down regulators (SERDs). It binds to the estrogen receptor (ER), with affinity close to that of estradiol and 100 fold greater than that of tamoxifen (a partial estrogen antagonist), preventing estrogen-stimulated gene activation, thereby interfering with the estrogenrelated processes essential for cell-cycle completion. Fulvestrant also appears to downregulate the ER by 80-90% often to non detectable level both in vitro and in vivo. In comparison to tamoxifen, fulvestrant is devoid of systemic estrogenic activity, it displays no uterotrophic activity and is able to block the uterine stimulation of estradiol or tamoxifen. Furthermore, fulvestrant completely blocks the cell growth in tamoxifen-resistant breast cancer cell-lines and prevents growth of tamoxifen resistant tumor in mice. In clinical trials, it was also shown that fulvestrant is comparable to anastrozole (a third generation aromatase inhibitor) both in efficacy and tolerability in postmenopausal women with tamoxifen-resistant advanced breast cancers.
Chemical PropertiesWhite or almost white powder.
OriginatorAstra Zeneca (UK)
Usesantiestrogen
UsesA novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).
DefinitionChEBI: A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.
Brand nameFaslodex (AstraZeneca).
General DescriptionFulvestrant, 7α-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17β-diol (Faslodex), is an antagonist structurally based onthe estradiol structure, with a long, substituted alkyl chainattached at the 7α-position of the steroid skeleton. Whenbound to the ERs, this alkyl chain induces a conformationof the receptor distinctive from that formed upon estradiolor tamoxifen binding, preventing agonist action.Fulvestrant is a pure antagonist at both ERαand ERβandan ER downregulator (stimulates degradation of the ER),completely lacking the agonist activity that is seen with tamoxifenor raloxifene. The different pharmacological profileof fulvestrant allows the use of this agent in womenwho have had disease progression after prior antiestrogentherapy (typically tamoxifen), providing an alternative toaromatase inhibitors.
Biological ActivityA high affinity estrogen receptor antagonist (IC 50 = 0.29 nM), devoid of any partial agonism both in vitro and in vivo . Also high affinity agonist at the membrane estrogen receptor GPR30.
Biochem/physiol ActionsFulvestrant (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.
Clinical UseTreatment of postmenopausal women with oestrogenreceptor- positive, locally advanced or metastatic breast cancer
Side effectsSide effects appear to be minimal and include several GI symptoms , headache, and hot flashes . There is no clinical evidence of uterine stimulation or laboratory evidence of stimulation of endometrial carcinoma models. Fulvestrant should not be adm inistered to women who are pregnant, who are taking antic oagulants, or who have thrombocytopenia.
SynthesisFulvestrant is administered as a once a month i. m. injection. Several routes for the synthesis of fulvestrant (12) were published. One of the best routes is depicted in the scheme. The conjugate addition of Grignard reagent derived from bromide 130 with dienone 129 gave adduct 131 as a mixture of 7α- and 7β-isomers in a ratio of 2.5:1 in 90-95% yield. Aromatization of the A-ring with copper bromide/lithium bromide in acetic acid followed by hydrolysis of the ester group provided diol 132 in 80-85% yield. Oxidation of the side chain from sulfite to sulfone followed by crystallization provided fulvestrant (12) in 30% overall yield from dienone 129.

Drug interactionsPotentially hazardous interactions with other drugs
None known
MetabolismThe metabolism of fulvestrant has not been fully evaluated, but involves combinations of a number of possible biotransformation pathways analogous to those of endogenous steroids. Identified metabolites (includes 17-ketone, sulphone, 3-sulphate, 3- and 17-glucuronide metabolites) are either less active or exhibit similar activity to fulvestrant in anti-oestrogen models.
Fulvestrant is eliminated mainly in metabolised form. The major route of excretion is via the faeces.
ReferencesOsborne et al. (2004), Fulvestrant: an oestrogen receptor antagonist with a novel mechanism of action; Br. J. Cancer 90 (Suppl 1):S2 Thomas et al. (2005), Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells; Endocrinology 146 624 Wardley (2002), Fulvestrant: a review of its development, pre-clinical and clinical data; Int. J. Clin. Pract. ?56 305 Castro et al. (2012),?Coumestrol has neuroprotective effects before and after cerebral ischemia in female rats; Brain Res.?1474 82 Blackburn et al. (2018),?Fulvestrant for the treatment of advanced breast cancer; Expert Rev. Anticancer Ther. 18 619
Tag:Fulvestrant(129453-61-8) Related Product Information
Fulvestrant 3-Sulfate Sodium Salt Fulvestrant 17-β-D-Glucuronide (7a,17b)-7-7-[9-[(4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]-estra-1,3,5(10)-triene-3,17-diol 17-acetate Fulvestrant 3-β-D-Glucuronide Fulvestrant 3-β-D-Glucuronide 17-Acetate FULVESTRANT-D3 FULVESTRANT(USAN) DIAMYL SULFOXIDE OCTADECYLMETHYLSULFIDE 4-tetradecylphenol 4-n-Octadecylphenol DODECYL METHYL SULFOXIDE OCTADECYL METHYL SULFOXIDE ETHYL OCTADECYL SULFIDE 4,4,5,5,5-Pentafluoro-1-pentanethiol p-hexadecylphenol 4-DODECYLPHENOL N-NONADECYLBENZENE