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Trilostane

treatment of Cushing's syndrome Uses in dogs Indications Treatment history Mechanism The treatment of advanced breast cancer
Trilostane
Trilostane structure
CAS No.
13647-35-3
Chemical Name:
Trilostane
Synonyms
Vetoryl;Desopan;modrenal;Modrefen;Win 24540;rilostane;TRILOSTANE;Modrastane;17-beta)-ph;Trilostane ,99%
CBNumber:
CB4768762
Molecular Formula:
C20H27NO3
Formula Weight:
329.43
MOL File:
13647-35-3.mol

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
CAS DataBase Reference
13647-35-3(CAS DataBase Reference)
FDA UNII
L0FPV48Q5R
Proposition 65 List
Trilostane
NCI Drug Dictionary
Modrastane
EPA Substance Registry System
Trilostane (13647-35-3)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H315-H319-H361
Precautionary statements  P281-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38-62
Safety Statements  26-36/37
WGK Germany  3
HS Code  29372900

Trilostane price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0141 Trilostane ≥98% (HPLC) 13647-35-3 10mg $108 2021-03-22 Buy
Sigma-Aldrich SML0141 Trilostane ≥98% (HPLC) 13647-35-3 50mg $452 2021-03-22 Buy
Cayman Chemical 14164 Trilostane ≥98% 13647-35-3 5mg $40 2021-03-22 Buy
Cayman Chemical 14164 Trilostane ≥98% 13647-35-3 10mg $76 2021-03-22 Buy
Cayman Chemical 14164 Trilostane ≥98% 13647-35-3 50mg $320 2021-03-22 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.

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

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

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


Trilostane Suppliers

Global( 258)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Baoji Guokang Bio-Technology Co., Ltd.
09173909592
09173909592 cngksw@aliyun.com CHINA 9446 58
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 sales@fine-chemtech.com CHINA 890 55
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20010 60
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8882 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26734 60
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29959 58
Tianjin Huiren Chemtech Co., Ltd
86-13672008665
86-22-23707858 huirentech@foxmail.com CHINA 110 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58
Changzhou Ansciep Chemical Co., Ltd.
+86 519 86305871
+86 519 86305879 sales@ansciepchem.com CHINA 4242 58

View Lastest Price from Trilostane manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-26 Trilostane
13647-35-3
US $0.00 / Kg/Bag 2Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
2021-10-26 Trilostane
13647-35-3
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-09-29 Trilostane
13647-35-3
US $0.00-0.00 / KG 100g 99%min 10KG WUHAN FORTUNA CHEMICAL CO., LTD

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