Trilostane
Basic information
- CAS
13647-35-3- Standard SMILES
C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C#N)C[C@]35C)[C@@H]1CC[C@@H]2O- InChIKey
KVJXBPDAXMEYOA-CXANFOAXSA-N- Molecular formula
- C20H27NO3
- Average molar mass
- 329.4 g/mol
- Monoisotopic mass
- 329.19909372
Overview
Trilostane can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Trilostane
- IUPAC
- (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile
- English name
- Trilostane
- Molecular formula
- C20H27NO3
- Molecular weight
- 329.43
Names & synonyms
Trilostane13647-35-3ModrenalDesopanVetorylTrilostanoModrastaneTrilostanumWin-24540WIN 24,540DTXSID9023706L0FPV48Q5R
Show more names
rilostaneTrilostan(1aS,4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,7-Dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrileModrefenTrostan*
Win 24540CHEBI:32260VETORYL CAPSULESNSC-758904Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4alpha,5alpha,17beta)-DTXCID1037064alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile
Database identifiers
- CAS
13647-35-3- PubChem CID
- 656583
- DTXSID
DTXSID9023706
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 76.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 692
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP3
Solubility5.93e-02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
EMA approved medicines: Veterinary medicine
EMA approved medicines: Veterinary medicine
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point264 °C
Physical DescriptionSolid
Collision Cross Section
186.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID9023706]
173.45 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P264, P264+P265, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Developmental Toxicity
Hazard Classes and CategoriesSkin Irrit. 2 (98%)
Safety data
- wgk
- 3
- hs_code
- 29372900
- risk_code
- 36/37/38-62
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xi
- safety_code
- 26-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H361
- Hazard Classifications
- Eye Irrit. 2Repr. 2Skin Irrit. 2
- Precautionary statements
- P201-P302+P352-P305+P351+P338-P308+P313
Chemistry & industry
Pharmacology
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins
QH - Systemic hormonal preparations, excl. sex hormones and insulin
Pharmacodynamics
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.
Mechanism of ActionTrilostane 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.
Biological Half-Life8 hours.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Steroidal compounds with abortifacient activity.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Cellular LocationsCytoplasm
Applications
Description3β-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 Ki 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.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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