Trilostan

Bezeichnung:Trilostan

CAS-Nr13647-35-3

Englisch Name:Trilostane

CBNumberCB4768762

SummenformelC20H27NO3

Molgewicht329.43

MOL-Datei13647-35-3.mol

Synonyma

Trilostan

Trilostan physikalisch-chemischer Eigenschaften

Schmelzpunkt	264 °C
alpha	D25 +137.4° (c = 1 in pyridine)
Siedepunkt	467.02°C (rough estimate)
Dichte	1.1213 (rough estimate)
Brechungsindex	1.5614 (estimate)
storage temp.	2-8°C
Löslichkeit	DMSO: ≥17mg/mL
Aggregatzustand	powder
pka	8.57±0.70(Predicted)
Farbe	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 Datenbank	13647-35-3(CAS DataBase Reference)
EPA chemische Informationen	Trilostane (13647-35-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-62
S-Sätze:	26-36/37
WGK Germany	3
HS Code	29372900

Gefahreninformationscode (GHS)

Trilostane Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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 K_i 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.
Chemische Eigenschaften
Tan Crystals
Originator
Modrenal,Sterling Winthrop,UK,1980
Verwenden
An inhibitor of steroid biosynthesis. Used as an adrenocortical suppressant. Used in the treatment of breast cancer.
Verwenden
antifungal, inhibits mitosis in metaphase
Verwenden
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.
Trademarks
Modrastane (Bioenvision).
Therapeutic Function
Corticosteroid antagonist
Allgemeine Beschreibung
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 Upstream-Materialien And Downstream Produkte

Trilostan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

13647-35-3, Trilostane Verwandte Suche:

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