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5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo-

Trilostane

CAS: 13647-35-3

Molecular Formula: C20H27NO3

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  5. 5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo-

5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo- - Names and Identifiers

Name Trilostane
Synonyms Vetoryl
Trilostane
TRILOSTANE
17-beta)-ph
17-hydroxy-3-oxo-4,5-epoxyandrostane-2-carbonitrile
4α,5-Epoxy-3,17β-dihydroxy-5α-androst-2-ene-2-carbonitrile
5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo-
(4a,5a,17b)-3,17-Dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile
Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4a,5a,17b)-
(4alpha,5alpha,17beta)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile
(2-alpha,4-alpha,5-alpha,17-beta)-4,5-epoxy-17-hydroxy-3-oxoandrostane-2-car
CAS 13647-35-3
EINECS 237-133-0
InChI InChI=1/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
InChIKey KVJXBPDAXMEYOA-CXANFOAXSA-N

5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo- - Physico-chemical Properties

Molecular FormulaC20H27NO3
Molar Mass329.43
Density1.1213 (rough estimate)
Melting Point264 °C
Boling Point467.02°C (rough estimate)
Specific Rotation(α)D25 +137.4° (c = 1 in pyridine)
Flash Point254.8°C
Solubility DMSO: ≥17mg/mL
Vapor Presure5.39E-12mmHg at 25°C
Appearancepowder
Colorwhite to tan
pKa8.57±0.70(Predicted)
Storage Condition2-8°C
Refractive Index1.5614 (estimate)
In vitro studyBoth Trilostane and 4-Hydroxytamoxifen (OHT) affect the transcription of genes involved in cell cycle regulation, cell adhesion, and matrix formation, however, only 12.5 percent of Trilostane down-regulated genes and 9.2 percent of up-regulated genes were similar in MCF-7 cells.
In vivo studyTrilostane treatment leads to a significant decrease in basal plasma cortisol concentration in dogs Trilostane treatment leads to a significant decrease in plasma aldosterone concentration (PAC) but median plasma renin activity (PRA(265 fmol/L/s) significantly higher than before treatment (115 fmol/L/s). Trilostane affects both the hypothalamic-pituitary-adrenal cortex and the renin-aldosterone axis. In Dahlsalt-sensitive rats, Trilostane was effective in increasing systolic blood pressure and reversing the high pressure generated in by drinking 0.9% saline. Trilostane was equally effective in female and male rats. In all cats, Trilostane reduced clinical symptoms and improved endocrine test results, but insulin requirements did not change, and all continued some signs of hypercortisolemia. In PDH dogs, Trilostane caused a decrease in serum cortisol and aldosterone concentrations, although the decrease in serum aldosterone concentrations was less than that of serum cortisol concentrations.

5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo- - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk CodesR36/37/38 - Irritating to eyes, respiratory system and skin.
R62 - Possible risk of impaired fertility
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37 - Wear suitable protective clothing and gloves.
WGK Germany3
HS Code29372900

5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo- - Reference Information

EPA chemical substance information information provided by: ofmpeb.epa.gov (external link)
indication triptan can inhibit 3 β-dehydrogenase in the process of corticosteroid synthesis, and reduce the synthesis of cortisol and aldosterone, it is clinically used to treat Cushing's syndrome (hypercortisolism) and primary aldosteronism, but it is not as effective as metilapone in treating Cushing's syndrome (hypercortisolism). This product also has a significant role in reducing blood testosterone levels, may be related to the inhibition of its synthesis.
treatment history , 5 α-epoxy-2-cyano-androst-2-ene-3, 17 β-diol reversibly inhibits 3 β-hydroxysteroid dehydrogenase and Δ5, 4-isomerase, which blocks the biosynthesis of mineralocorticoids and glucocorticoids, was approved in the UK in 1980 for the treatment of hyperaldosteronism and hypercortisolism, it was approved for the treatment of Cushing's syndrome or hyperadrenocortical syndrome in the United States in 1985. Given that older animals, especially older dogs, are predisposed to Cushing's syndrome, and that trolostine can alleviate symptoms and improve quality of life in more than 90% of dogs, so the drug is also approved for veterinary use in the UK. Triptan itself has no hormonal activity, so its side effects are less, and its safety and tolerability are particularly good.
mechanism of action Breast cancer is a hormone-dependent tumor, and estrogen is the main driver of cancer cell growth. Therefore, one of the modern major therapies for breast cancer is to target estrogen by inhibiting estrogen production or blocking the action of estrogen at its site of action, the estrogen receptor. The estrogen receptor has been considered to be a single receptor, but recent studies have identified at least two subtypes, alpha and beta. Estrogen binding to α-estrogen receptor can stimulate cell growth, but binding to β-estrogen receptor can down-regulate α-estrogen receptor and slow down cell proliferation rate. Studies have revealed that in addition to reducing the production of estrogen, triptan can also regulate the binding of estrogen to different subtypes of estrogen receptors, at the same time, the dual effects of α-estrogen receptor inhibitor and β-estrogen receptor agonist are manifested, and the negative effect of estrogen on cancer cells is finally blocked and changed. The unique mode of action of triptan not only distinguishes it from other anti-estrogens currently available, but is also the pharmacological basis for its still highly effective treatment of failed or resistant breast cancer with other anti-estrogen therapies.
treatment of advanced breast cancer Breast cancer is the most common tumor type in women. At present, for postmenopausal patients with hormone receptor-positive or unknown type of breast cancer, clinical consistently recommend the preferred anti-estrogen therapy, and this therapy in patients with disease progression, the role of improving survival time has long been affirmed and confirmed by a large number of studies. A new drug, modlenal, developed by Bioenvision, a biotechnology company, is available to treat postmenopausal women whose hormone-selective cancer has spread outside the mammary gland, the drug is administered in two ways to slow disease progression. For hormone-sensitive breast cancer, estrogen promotes the growth of cancer cells by acting on two receptors. Estrogen а is like a cancer accelerator, and estrogen receptor β is a brake. Modrenal enhances the adsorption of estrogen to estrogen receptor beta and attenuates the effect on estrogen receptor а. It also acts on another site on the cell's DNA, AP1, to reduce cell proliferation.
biological activity Trilostane (WIN 24540) is a 3β hydroxysteroid dehydrogenase inhibitor used in the treatment of Cushing's syndrome.
TargetValue
Last Update：2024-04-09 20:52:54
5a-Androstane-2a-carbonitrile, 4a,5-epoxy-17b-hydroxy-3-oxo-
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