SML0141

Trilostane

≥98% (HPLC)

• Synonym(s): (4α,5α,17β)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile
• Empirical Formula (Hill Notation): C₂₀H₂₇NO₃
• CAS Number: 13647-35-3
• Molecular Weight: 329.43
• EC Number: 237-133-0
• MDL number: MFCD00199295
• UNSPSC Code: 51111800
• PubChem Substance ID: 329825189
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: white to tan
• solubility: DMSO: ≥17 mg/mL
• storage temp.: 2-8°C
• SMILES string: C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C[C@]35C)C#N)[C@@H]1CC[C@@H]2O
• InChI: 1S/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
• InChI key: KVJXBPDAXMEYOA-CXANFOAXSA-N
• Gene Information: human ... HSD3B2(3284)

Description

General description

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

Application

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

Trilostane was used to inhibit the activity of 3β-hydroxysteroid dehydrogenase in mouse ovary.

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.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H361
• Precautionary Statements: P202 - P264 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable