ChemicalBook >> CAS DataBase List >>Formestane

Formestane

CAS No.
566-48-3
Chemical Name:
Formestane
Synonyms
4-OHA;CYPXIX;LENTARON;CGP-32349;P-450AROM;FORMESTANE;FROMESTANE;NSC 282175;Stan FuMei;FORMESTAQNE
CBNumber:
CB6251183
Molecular Formula:
C19H26O3
Molecular Weight:
302.41
MDL Number:
MFCD00057814
MOL File:
566-48-3.mol
MSDS File:
SDS
Last updated:2024-02-28 17:23:02

Formestane Properties

Melting point 199-202°C
alpha D20 +181° (c = 7.7 in chloroform)
Boiling point 383.44°C (rough estimate)
Density 1.1189 (rough estimate)
refractive index 1.4200 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form solid
pka 9.31±0.60(Predicted)
color White to Off-White
InChI InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
InChIKey OSVMTWJCGUFAOD-KZQROQTASA-N
SMILES C1(=O)C(O)=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(=O)CC3)CC2
CAS DataBase Reference 566-48-3(CAS DataBase Reference)
FDA UNII PUB9T8T355
NCI Drug Dictionary formestane
ATC code L02BG02

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H360
Precautionary statements  P201-P308+P313
Hazard Codes  T
Risk Statements  60
Safety Statements  53-36/37/39-45
WGK Germany  3
RTECS  BV8152500

Formestane price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SAB4500606 Anti-Cytochrome P450 19A1 antibody produced in rabbit affinity isolated antibody 566-48-3 100μG $506 2024-03-01 Buy
Sigma-Aldrich F2552 Formestane solid 566-48-3 1g $239 2024-03-01 Buy
Cayman Chemical 18282 4-hydroxy Androstenedione ≥98% 566-48-3 100mg $32 2024-03-01 Buy
Cayman Chemical 18282 4-hydroxy Androstenedione ≥98% 566-48-3 1g $184 2024-03-01 Buy
Cayman Chemical 18282 4-hydroxy Androstenedione ≥98% 566-48-3 500mg $116 2024-03-01 Buy
Product number Packaging Price Buy
SAB4500606 100μG $506 Buy
F2552 1g $239 Buy
18282 100mg $32 Buy
18282 1g $184 Buy
18282 500mg $116 Buy

Formestane Chemical Properties,Uses,Production

Anti-cancer drugs

Formestane also known as lentaron,is an anti-cancer drug, it is primarily used for the treatment of postmenopausal women with advanced breast cancer, it is also effective in prostate cancer.
Formestane is a androstenedione derivative, and it belongs to an aromatase inhibitor with aminoglutethimide, it is a hormone antineoplastic agent. In physiological conditions, it may competitively inhibit the synthesis of the enzyme leading to estrogen biosynthesis decrease in tissues, then it plays its role in cancer. When the tumor tissue growth relies on the presence of estrogen, in order to inhibit tumor growth, the elimination of tumor estrogen-mediated growth stimulation is necessary. This product is more selective than aminoglutethimide while its activity is 100 to 1000 times of aminoglutethimide, and it does not inhibit the synthesis of adrenal hormones,without having to recharge cortisone, etc . The in vitro inhibition of aromatase enzyme of this product is 60 times stronger than aminoglutethimide.
While it is used alone, the drug can not significantly reduce the pre-menopausal estrogen levels in the blood of women,when it is combined with goserelin (gonadotropin-releasing hormone agonist), its inhibitory effect of estrogen in premenopausal women is greater than goserelin used alone. Formestane has no cross-resistance with other aromatase inhibitors , it has no side effects of aminoglutethimide. After oral administration,it is rapidly absorbed by gastrointestinal, its peak plasma concentration time is 1 to 1.5 hours, but the peak concentration of individual is of great difference; after intramuscular injection,it can be accumulated at the injection site and be slowly absorbed. It performs Biphasic elimination process, the initial elimination half-life is 2 to 4 days, the terminal elimination half-life is 5 to 10 days. It is mainly metabolized in the liver after oral administration, in the form of glycosides acid metabolites excreted in the urine.
The above information is edited by the chemicalbook of Tian Ye.

Chemical Properties

Crystallized from aqueous methanol, m.p. 199~202 ℃; crystallized from ethyl acetate, m.p. 203.5~206 ℃. UV absorption maximum (99.5% ethanol): 278nm (ε11030). [α] D20 + 181 ° (C = 7.7, chloroform).

Uses

aromatase inhibitors ,it is used for progressive breast cancer.
male hormones, assimilating protein class.

production method

Androst-4-ene-3,17-dione (Ⅰ) (1.432g, 5mmo1) is dissolved in 50ml tert-butanol ,add 38mg (0.15mmo1) osmium tetroxide in 2ml t-butanol solution at room temperature, and then 5ml 35% hydrogen peroxide is added, followed by stirring at room temperature for 3 days. After dilution of 100ml brine, and extract with dichloromethane (2 × 100m1). The extract is washed with 100ml brine, , 50ml 10% sodium bisulfite solution, 50ml 10% sodium carbonate solution and 100ml brine, dry over anhydrous sodium sulfate, and concentrate. The residue (1.824g) of the compound (Ⅱ), is dissolved in methanol (10ml),add potassium hydroxide (393mg, 7mmo1) in 3ml methanol . Plus Albert, stirring 10min at 55 ℃. Add 0.3ml of acetic acid and 100ml of brine, and extract with dichloromethane (2 × 100ml). Complex solution, combine, wash with 100ml brine, dry with anhydrous sodium sulfate, and concentrate. The residue (1.727g) by column chromatography on silica gel, wash with hexane-ethyl acetate (7: 3) to give 715mg formestane, yield 47%, mp 200~202 ℃ (acetone).

Description

Formestane is a potent aromatase inhibitor launched in the UK as a second-line endocrine treatment for breast cancer. As a synthetic derivative of androstanedione, the natural substrate for the biosynthesis of estrogen by the enzyme aromatase, formastane selectively inhibits aromatase and binds to its steroid receptor site to cause a rapid and sustained fall in circulating estrogen level and, therefore, inhibits tumor growth. In patients with existing bulky primary tumors, formestane effectively reduces the size of the tumors. Formastane has apparent tolerability advantages and less side effects than other agents such as aminoglutethimide.

Description

4-hydroxy Androstenedione (4-HAD) is a steroidal inhibitor of aromatase (also known as cytochrome P450 19A1; Ki = 27 nM). As aromatase catalyzes the conversion of androgens to estrogens, aromatase inhibitors, including 4-HAD, are used against hormone-sensitive breast cancer in menopausal women. They are also abused in combination with anabolic steroids in racehorses and athletes. This product is intended for forensic and research applications.

Chemical Properties

Needles

Originator

Ciba-Geigy (Switzerland)

History

Formestane is a second-generation steroidal aromatase inhibitor, and the first one to reach clinical use during the early 1990s[1].

Uses

An antitumor drug. An aromatase inhibitor.

Uses

antineoplastic, aromatase inhibitor

Definition

ChEBI: A 17-oxo steroid that is androst-4-ene-3,17-dione in which the hydrogen at position 4 is replaced by a hydroxy group. Formestane was the first selective, type I steroidal aromatase inhibitor, suppressing oestrogen production from anabolic steroids or proho mones. It was formerly used in the treatment of oestrogen-receptor positive breast cancer in post-meopausal women. As it has poor oral bioavailability, it had to be administered by (fortnightly) intramuscular injection. It fell out of use with the subseque t development of cheaper, orally active aromatase inhibitors. Formestane is listed by the World Anti-Doping Agency as a substance prohibited from use by athletes.

brand name

Lentaron

Mechanism of action

Aromatase inhibitors such as formestane and letrozole reduce plasma estradiol levels by inhibiting the conversion of testosterone to estrogen. This compound was first described as a competitive inhibitor, but subsequent evidence proved that its binding to aromatase was irreversible. Hence, it is a suicide inhibitor. In the dog, but not rodents, this results in Leydig cell hypertrophy and hyperplasia. This is thought to be due to the differential sensitivity of the pituitary feedback mechanism to estrogens and androgens in the different species[1-2].

References

[1] Avenda?o C, et al. Anticancer Drugs That Inhibit Hormone Action. Medicinal Chemistry of Anticancer Drugs, 2008; 53-91.0
[2] Berczi I, et al. Biologically Controlled Mutations are Right for Evolution. Insights to Neuroimmune Biology, 2016; 217-241.

63-05-8
566-48-3
Synthesis of Formestane from Androstenedione
Global( 255)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
+86-13288715578 +86-13231137666 sales@hbmojin.com China 12409 58
Hong Kong Excellence Biotechnology Co., Ltd.
+86-86-18838029171 +8618126314766 ada@sh-teruiop.com China 892 58
Nantong Guangyuan Chemicl Co,Ltd
+undefined17712220823 admin@guyunchem.com China 616 58
Sigma Audley
+86-18336680971 +86-18126314766 nova@sh-teruiop.com China 501 58
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
Rixing Chemical CO.,LTD
+86-13237129059 -13237129059 sales@rixingchemi.com CHINA 229 55
Shanxi Naipu Import and Export Co.,Ltd
+86-13734021967 +8613734021967 kaia@neputrading.com China 1011 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29919 58
.GZ HONESTCHEM CO.,LTD
+86-15013270415 honestchemical@foxmail.com China 245 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503282 alice@crovellbio.com China 8823 58

View Lastest Price from Formestane manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Formestane pictures 2024-03-16 Formestane
566-48-3
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Formestane pictures 2024-03-15 Formestane
566-48-3
US $100.00 / kg 1kg 99.9% 20tons Hong Kong Excellence Biotechnology Co., Ltd.
Formestane pictures 2024-03-08 Formestane
566-48-3
US $10.00 / kg 1kg 99% 1000kg Nantong Guangyuan Chemicl Co,Ltd
  • Formestane pictures
  • Formestane
    566-48-3
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Formestane pictures
  • Formestane
    566-48-3
  • US $100.00 / kg
  • 99.9%
  • Hong Kong Excellence Biotechnology Co., Ltd.
  • Formestane pictures
  • Formestane
    566-48-3
  • US $10.00 / kg
  • 99%
  • Nantong Guangyuan Chemicl Co,Ltd

Formestane Spectrum

4-hydroxy-androst-4-ene-17-dione 4-hydroxy-delta(sub4)-androstenedione 4-HYDROXYANDROST-4-ENE-3,17-DIONE 4-HYDROXYANDROSTENEDIONE 4-HYDROXY-4-ANDROSTENE-3,17-DIONE 4-ANDROSTEN-4-OL-3,17-DIONE 4-OHA CGP-32349 FROMESTANE FORMESTANE FORMESTAQNE LENTARON Formesatane FORMESTANE 98% FORMESTANE,4-HYDROXYANDROST-4-ENE-3,17-DIONE 4-ANDROSTENE-4-OL-3,17-DIONE 4-Hydroxyandrost-4-ene-3,17-dione, 4-OHA, CGP-32349, Lentaron FORMASTANE/FORMESTANE/4-ANDROSTEN-4-OL-3,17-DIONE 4-ANDROSTEN-4-OL-3,17-DIONE(FORMESTANE) B, Aromatase inhibitor 6-hydroxy-10,13-dimethyl- 1,7,8,9,10,11,12,13,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17(6H,14H)-dione 4-Hydroxyandrost-4-ene-3,17-dione, CGP-32349 4-Hydroxyandrostan-4-ene-3,17-dione (8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione (8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-quinone 4-Hydroxy-4-androstenedione 4-Hydroxyandrostendione (Formestane) NSC 282175 CGP-32349:Lentaron Androst-4-ene-3,17-dione,4-hydroxy- Stan FuMei (8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-1,7,8,9,10,11,12,13,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17(6H,14H)-dione Anti-Cytochrome P450 19A1 antibody produced in rabbit CYPXIX Cytochrome P450 19A1 Estrogen synthetase P-450AROM Lentaron Formestane Formestane on sale CAS NO.566-48-3 Formestane ,Lentaron Formestane cas 566-48-3 (skype:lisa_21819) Formestane 566-48-3 Formestane USP/EP/BP Anti-Estrogens Steroids Raw Powder Formestane Formestane(4-hydroxy-androstenedione) Formestane (CGP-32349) TIANFU CHEM- Formestane Formestane Lentaron Raw Powder 566-48-3 Enzymes, Inhibitors, and Substrates Enzyme Inhibitors Enzyme Inhibitors by Enzyme 多肽抗原 小鼠抗人和大、小鼠、犬、猪、牛芳香化酶多克隆抗体 Aromatase A to C Biochemicals and Reagents BioChemical