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Trilostane

Trilostane structure

CAS No:
13647-35-3
Formula:
C20H27NO3
Chemical Name:
Trilostane
Synonyms:
Androst-2-ene-2-carbonitrile,4,5-epoxy-3,17-dihydroxy-,(4α,5α,17β)-;(4α,5α,17β)-4,5-Epoxy-3,17-dihydroxyandrost-2-ene-2-carbonitrile;Trilostane;Win 24540;Modrenal;Modrefen;Desopan;Modrastane;Vetoryl;27107-98-8;28414-46-2
Categories:
Inorganic Chemistry > Inorganic Salts

Description

Tan CrystalsTrilostane 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.

Solid

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.|Trilostane is an inhibitor of 3 beta-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome. It was withdrawn from the United States market in April 1994.|Trilostane is a synthetic derivative of androstane with adrenocortical suppressive properties. Trilostane reversibly inhibits 3 beta-hydroxysteroid dehydrogenase delta 5-4 isomerase in the adrenal cortex, resulting in the decreased synthesis of mineralocorticoids and glucocorticoids and the decreased conversion of pregnenolone to progesterone. (NCI04)

Trilostane Basic Attributes

Molecular Weight：

329.43

Exact Mass：

329.43

EC Number：

237-133-0

UNII：

L0FPV48Q5R

DSSTox ID：

DTXSID9023706

NCI Thesaurus Code：

C1263

ATC Code：

H - Systemic hormonal preparations, excl. sex hormones and insulins

HScode：

29372900

Characteristics

PSA：

76.8

XLogP3：

Appearance：

white to tan

Density：

1.1213 (rough estimate)

Melting Point：

264 °C (decomp)

Boiling Point：

467.02°C (rough estimate)

Flash Point：

254.8±28.7 °C

Refractive Index：

1.5614 (estimate)

Water Solubility：

DMSO: ≥17mg/mL

Storage Conditions：

-20°C Freezer

Specific rotation：

D25 +137.4° (c = 1 in pyridine)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-62

safety instructions：

26-36/37

Marks：

Precautionary statement(s)：

P281-P305 + P351 + P338

Hazard Statements：

H315-H319-H361

GHS Classification：

|Warning|H315 (97.73%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P321, P332+P313, P337+P313, P362, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Symptoms of overdose include darkening of skin, drowsiness or tiredness, loss of appetite, mental depression, skin rash, and/or vomiting.

Drug Information

Drug Indication：

Used in the treatment of Cushing's syndrome. It is normally used in short-term treatment until permanent therapy is possible.

Pharmacology：

Trilostane blocks an enzyme involved in the production of several steroids including cortisol. Inhibiting this enzyme inhibits the production of cortisol. In Cushing's syndrome, the adrenal gland overproduces steroids. Although steroids are important for various functions of the body, too much can cause problems. Trilostane reduces the amount of steroids produced by the adrenal gland. This product was withdrawn from the U.S. market in April 1994.

MeSH：

Steroidal compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Steroidal.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Metabolism/Metabolites：

Hepatic.

Biological Half-Life：

8 hours.

Mechanism of Action：

Trilostane produces suppression of the adrenal cortex by inhibiting enzymatic conversion of steroids by 3-beta-hydroxysteroid dehydrogenase/delta 5,4 ketosteroid isomerase, thus blocking synthesis of adrenal steroids.

MeSH Entry Terms：

4alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile

Trilostane Use and Manufacturing

Uses

antifungal, inhibits mitosis in metaphase

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:329.4
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:329.19909372
Monoisotopic Mass:329.19909372
Topological Polar Surface Area:76.8
Heavy Atom Count:24
Complexity:692
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Trilostane

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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