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ChemicalBook >> CAS DataBase List >>Trilostane

Trilostane

CAS No.
13647-35-3
Chemical Name:
Trilostane
Synonyms
Vetoryl;Desopan;modrenal;Modrefen;Trostan*;Win 24540;rilostane;Trilostan;TRILOSTANE;Modrastane
CBNumber:
CB4768762
Molecular Formula:
C20H27NO3
Molecular Weight:
329.43
MDL Number:
MFCD00199295
MOL File:
13647-35-3.mol
MSDS File:
SDS
Last updated:2024-10-29 20:19:27

Trilostane Properties

Melting point 264 °C
alpha D25 +137.4° (c = 1 in pyridine)
Boiling point 467.02°C (rough estimate)
Density 1.1213 (rough estimate)
refractive index 1.5614 (estimate)
storage temp. 2-8°C
solubility DMSO: ≥17mg/mL
form powder
pka 8.57±0.70(Predicted)
color white to tan
InChIKey KVJXBPDAXMEYOA-CXANFOAXSA-N
SMILES [C@@]123CC[C@@]4([H])[C@]5([H])CC[C@H](O)[C@@]5(C)CC[C@]4([H])[C@@]1(C)CC(C#N)=C(O)[C@@]2([H])O3 |&1:0,3,5,9,11,15,17,25,r|
CAS DataBase Reference 13647-35-3(CAS DataBase Reference)
FDA UNII L0FPV48Q5R
NCI Drug Dictionary Modrastane
ATC code H02CA01
Proposition 65 List Trilostane
EPA Substance Registry System Trilostane (13647-35-3)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H315-H319-H361
Precautionary statements  P201-P302+P352-P305+P351+P338-P308+P313
Hazard Codes  Xi
Risk Statements  36/37/38-62
Safety Statements  26-36/37
WGK Germany  3
HS Code  29372900
NFPA 704
0
2 0

Trilostane price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0141 Trilostane ≥98% (HPLC) 13647-35-3 10mg $129 2024-03-01 Buy
Sigma-Aldrich SML0141 Trilostane ≥98% (HPLC) 13647-35-3 50mg $539 2024-03-01 Buy
Cayman Chemical 14164 Trilostane ≥98% 13647-35-3 5mg $50 2024-03-01 Buy
Cayman Chemical 14164 Trilostane ≥98% 13647-35-3 10mg $94 2024-03-01 Buy
Cayman Chemical 14164 Trilostane ≥98% 13647-35-3 50mg $389 2024-03-01 Buy
Product number Packaging Price Buy
SML0141 10mg $129 Buy
SML0141 50mg $539 Buy
14164 5mg $50 Buy
14164 10mg $94 Buy
14164 50mg $389 Buy

Trilostane Chemical Properties,Uses,Production

treatment of Cushing's syndrome

Trilostane is an inhibitor of 3β-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome and primary hyperaldosteronism. These are both disorders where excess amounts of corticosteroid hormones are produced in the body. Corticosteroids are essential for the body to make use of carbohydrates, fats and proteins and for a normal response to stress. They are also necessary for the regulation of salt and water balance in the body. Trilostane helps prevent the production of corticosteroids, controlling the symptoms associated with these disorders.
Trilostane can also be useful in the treatment of breast cancer that has relapsed in women who have gone through menopause.

Uses in dogs

Trilostane was withdrawn from the United States market in April 1994. However, it was approved in 2008 for the treatment of Cushing's disease (hyperandrenocorticism) in dogs.
It is also the first drug approved to treat both pituitary-and adrenal-dependent Cushing's in dogs.
1. has kidney or liver disease.
2. takes certain medications used to treat heart disease.
3. pregnant.
4. taking other medicines, including those available to buy without a prescription, herbal or complementary medicines.
5. had an allergic reaction to this or any other medicine.

Indications

Trilostane can inhibit 3β-dehydrogenase in the synthesis of corticosteroids, and decrease the synthesis of cortisol and aldosterone. It also can be used in the treatment of Cushing's syndrome (hypercortisolism) and primary aldosteronism. But the efficacy to treat Cushing's syndrome (hypercortisolism) is not as metyrapone. This product also has a significant role in lowering blood testosterone levels, which may be related with that its synthesis is inhibited.

Treatment history

Trilostane, that is 4α, 5α-epoxy-2-cyano-3,17β-diol, can reversibly inhibit 3β-hydroxy steroid dehydrogenase and △5, 4-isomerase in the adrenal cortex to block the biosynthesis of mineralocorticoid and glucocorticoid. In 1980, it was approved for the treatment of hyperaldosteronism and cortisol excess disease in the United Kingdom. In 1985, it was approved for the treatment of Cushing's syndrome in the United States, which is adrenal cortex hyperactivity disorder. In view of the older animals, especially older dogs are susceptible to Cushing's syndrome. Trilostane can relieve the disease symptoms of more than 90% of dogs, and improve their quality of life. So the drug has also been granted for the treatment of animals in the United Kingdom. Trilostane itself has no hormonal activity. Its side effects is less, and its safety and tolerability are also particularly good.
The above information is edited by the chemicalbook of Ge Qian.

Mechanism

Breast cancer is one of hormone-dependent tumors. And estrogen is the main driving factor of the growth of breast cancer cells. Thus, one of the modern treatment of breast cancer is the major target of estrogen through inhibiting the production of estrogen or block the action of estrogen or estrogen receptor in its site of action. It has been known that estrogen receptor is only a single receptor, but recent studies have identified that there are at least two subtypes α and β. Estrogen uniting with α-estrogen can stimulate cell growth, but it uniting with β-estrogen receptor can cut α-estrogen receptors and slow the rate of cell proliferation. Research revealed that the trilostane cannot only lower the production of estrogen, but also can modulate the binding of estrogen receptors on different subtypes. And meanwhile the dual effect of α-estrogen receptor inhibitors and β-estrogen receptor appears. Finally it can block and alter the negative effect of estrogen on cancer cells. The unique mode of action of trilostane can not only set it apart from other existing anti-estrogen drugs, but also be the pharmacological basis of that it is still highly effective on breast cancer in treatment failure with other anti-estrogen therapy or resistant breast cancer.

The treatment of advanced breast cancer

Breast cancer is the most common type of tumor in women. Currently, for postmenopausal patients with hormone receptor-positive or unknown, clinical treatments unanimously recommend to be the preferred antiestrogen therapy, and the role of this therapy in delaying disease progression and improving survival time also has been affirmed and confirmed in numerous studies of breast cancer.
Trilostane (trade name Modrenal) developed by the biotechnology company has already been on the market. It can be used for the treatment of postmenopausal women that hormone-selective cancer has spread outside the breast. The pharmaceutical uses two ways to slow down the disease progression. For hormone-sensitive breast cancer, estrogen promotes the growth of cancer cells by acting to the two receptors. Estrogen receptor α is cancer accelerator, and estrogen receptor β is the brake. Modrenal strengthens estrogen adsorption to the estrogen receptor β, and weakens the adsorption to estrogen receptor α. Meanwhile it also acts on another loci AP1in cell DNA to reduce cell proliferation.

Description

3β-hydroxysteroid dehydrogenase (3β-HSD) type 1 and type 2 isoforms are key enzymes for the biosynthesis of all active steroid hormones. 3β-HSD1 (type I) is expressed in placenta and peripheral tissues including breast tumors, whereas 3β-HSD2 (type 2) is expressed in the adrenal gland, ovary, and testis. Trilostane is an inhibitor of the 3β-HSDs: 3β-HSD1 and 3β-HSD2 with Ki values of 0.10 and 1.60 μM, respectively. Trilsotane has been approved for use in the treatment of Cushing’s syndrome in dogs to reduce cortisol, aldosterone, and corticosterone levels. Because human 3β-HSD (type 1) is a critical enzyme in the conversion of DHEA to estradiol in breast tumors, trilostane is also of interest for the treatment of breast cancer in postmenopausal women.

Chemical Properties

Tan Crystals

Originator

Modrenal,Sterling Winthrop,UK,1980

Uses

An inhibitor of steroid biosynthesis. Used as an adrenocortical suppressant. Used in the treatment of breast cancer.

Uses

antifungal, inhibits mitosis in metaphase

Uses

Trilostane has been used to evaluate its capability to regulate the sex-dependent differences in the lipopolysaccharide (LPS)-induced inflammatory responses of astrocytes.

Definition

ChEBI: Trilostane is an epoxy steroid that is 3,17beta-dihydroxy-5alpha-androst-2-ene-2-carbonitrile in which the oxygen of the epoxy group is joined to the 4alpha and 5 alpha positions. It has a role as an antineoplastic agent, an abortifacient and an EC 1.1.1.210 [3beta(or 20alpha)-hydroxysteroid dehydrogenase] inhibitor. It is a 3-hydroxy steroid, a 17beta-hydroxy steroid, an androstanoid, an epoxy steroid and a nitrile.

Manufacturing Process

(A)17β-acetoxy-4α,5α-epoxyandrostano[2,3-d]isoxazole, melting point 228.6°C to 229.8°C (corrected) recrystallized from a benzene-methanol mixture, [α]D25 = +76.5°C (1% in chloroform), was prepared by treating 17β- acetoxy-4-androsteno[2,3-d] isoxazole with maleic anhydride and hydrogen peroxide in methylene dichloride solution.
(B)2α-cyano-4α,5α-epoxandrostan-17β-ol-3-one was prepared by treating 17β-acetoxy-4α,5α-epoxyandrostano[2,3-d] isoxazole with sodium methoxide, and was obtained in the form of tan crystals, melting point 257.8°C to 270.0°C (decomposition) (corrected) when recrystallized from a pyridine_x0002_dioxane mixture.

brand name

Modrastane (Bioenvision).

Therapeutic Function

Corticosteroid antagonist

General Description

Trilostane inhibits the production of adrenal steroids, such as cortisol and aldosterone. It is used to treat aldosteronism.

Biochem/physiol Actions

Trilostane is an inhibitor of 3 β-hydroxysteroid dehydrogenase (3-β-HSD or delta 5-delta 4-isomerase), an essential enzyme for the biosynthesis of all classes of hormonal steroids. It has been used in the treatment of Cushing′s syndrome for stopping the production of cortisol, and is currently approved for dogs in the US, but is still a human drug in the UK and other countries. It is being investigated as a possible treatment for both breast cancer and prostate cancer to prevent the synthesis of estrogens and androgens from endogenous precursors. It has also been used to inhibit endogenous production of progesterone in research studies.

Veterinary Drugs and Treatments

Trilostane may be useful for treating pituitary-dependent hyperadrenocorticism or adrenal dependent hyperadrenocorticism in dogs, feline pituitary-dependent hyperadrenocorticism, and equine hyperadrenocorticism (HAC). It may also be useful in treating Pomeranians with Alopecia X and Alaskan malamutes with adultonset alopecia.

Trilostane Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 360)Suppliers
Supplier Tel Email Country ProdList Advantage
Baoji Guokang Bio-Technology Co., Ltd.
0917-3909592 13892490616 gksales1@gk-bio.com China 9315 58
Tianjin Kilo Pharmaceutical Sci-Tech Co., Ltd
+86-02223869539 +86-15560057295 trade.kilopharma@foxmail.com China 27 58
Liaoning Pharmaceutical Innovation Co., Ltd
+8616588669988 sales@pipharma.com.cn China 151 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5858 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2472 58
Shaanxi Haibo Biotechnology Co., Ltd
+undefined18602966907 qinhe02@xaltbio.com China 997 58
Hebei Mojin Biotechnology Co.,Ltd
+86-15028179902 angelia@hbmojin.com China 1179 58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
+86-18600796368 +86-18600796368 sales@sjar-tech.com China 375 58
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806 sales@capot.com China 29791 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21639 55

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View Lastest Price from Trilostane manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Trilostane pictures 2024-10-30 Trilostane
13647-35-3
US $0.00 / Kg/Bag 2Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
Trilostane pictures 2024-10-30 Trilostane
13647-35-3
US $0.00-0.00 / KG 100g 99%min 10KG WUHAN FORTUNA CHEMICAL CO., LTD
Trilostane pictures 2024-10-29 Trilostane
13647-35-3
US $33.00-53.00 / mg 100% 10g TargetMol Chemicals Inc.
  • Trilostane pictures
  • Trilostane
    13647-35-3
  • US $0.00 / Kg/Bag
  • 99% up, High Density
  • Sinoway Industrial co., ltd.
  • Trilostane pictures
  • Trilostane
    13647-35-3
  • US $0.00-0.00 / KG
  • 99%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Trilostane pictures
  • Trilostane
    13647-35-3
  • US $33.00-53.00 / mg
  • 100%
  • TargetMol Chemicals Inc.

Trilostane Spectrum

TRILOSTANE (2-alpha,4-alpha,5-alpha,17-beta)-4,5-epoxy-17-hydroxy-3-oxoandrostane-2-car 17-beta)-ph (4a,5a,17b)-3,17-Dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile 5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo- Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4a,5a,17b)- 4α,5-Epoxy-3,17β-dihydroxy-5α-androst-2-ene-2-carbonitrile 4α,5-Epoxy-3,17β-dihydroxy-5α-androstan-2-ene-2-carbonitrile Trilostane ,99% modrenal Win-24540,Desopan,Modrastane,Modrenal 4,5-Epoxy-5H-cyclopenta[a]phenanthrene, androst-2-ene-2-carbonitrile deriv. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4a,5a,17b)- (9CI) Desopan Modrastane Modrefen Win 24540 (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-diMethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)- (4α,5α,17β)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile 4-alpha,5-epoxy-17-beta-hydroxy-3-oxo-5-alpha-androstane-2-alpha-carbonitril 4-alpha,5-epoxy-3,17-dihydroxy-5-alpha-androst-2-ene-2-carbonitrile 4-alpha-5-epoxy-17-beta-hydroxy-3-oxo-5-alpha-androstane-2-alpha-carbonitril androstane-2-carbonitrile,4,5-epoxy-17-hydroxy-3-oxo-,(2-alpha,4-alpha,5-al Trilostane(Win 24540 MODRASTANE; MODREFEN; MODRENAL; VETORYL; WIN 24540 Trilostane (Mixture of Tautomeric Isomers) rilostane Trilostane ISO 9001:2015 REACH Trilostan Vetoryl Tralostatin Trilostane/Win24540/Modrastane (1aS,4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,7-Dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile Trostan* Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)- 13647-35-3 3647-35-3 Intermediates & Fine Chemicals Pharmaceuticals Steroids Inhibitor FULVICIN APIs