Tixocortol
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Grundinformationen
- CAS
61951-99-3- Standard-SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CS- InChIKey
YWDBSCORAARPPF-VWUMJDOOSA-N- Summenformel
- C21H30O4S
- Durchschnittliche Molmasse
- 378,5 g/mol
- Monoisotopische Masse
- 378,18648044
Überblick
Tixocortol is a steroid sulfide in which the sulfanyl group is at C-21 of a polyoxygenated derivative of pregn-4-ene. It has a role as a glucocorticoid receptor agonist. It is a tertiary alpha-hydroxy ketone, a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a steroid sulfide. It derives from a hydride of a pregnane.
Namen und Bezeichner
- Bevorzugter Name
- Tixocortol
- IUPAC
- (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-17-(2-sulfanylacetyl)-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
- Englischer Name
- Tixocortol
- Summenformel
- C21H30O4S
- Molmasse
- 378.53
Namen und Synonyme
Tixocortol61951-99-3TixocortolumZX3KEK657Z11beta,17-dihydroxy-21-sulfanylpregn-4-ene-3,20-dioneCHEBI:63560DTXSID30895062Pregn-4-ene-3,20-dione, 11,17-dihydroxy-21-mercapto-, (11beta)-RefChem:190184A07EA05R01AD07DTXCID101324618
Weitere Namen anzeigen
Cortisol 21-Thiol11β,17-Dihydroxy-21-Mercaptoprogesterone(11β)-11,17-Dihydroxy-21-Mercaptopregn-4-ene-3,20-dionePregn-4-ene-3,20-dione, 11,17-dihydroxy-21-mercapto-, (11β)-
612-814-9Tixocortol (INN)(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-1-(2-sulfanylacetyl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-17-(2-sulfanylacetyl)-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one(11beta)-11,17-dihydroxy-21-mercaptopregn-4-ene-3,20-dioneTIXOCORTOL [INN]Tixocortol [INN:BAN]Tixocortolum [INN-Latin]
Datenbank-Bezeichner
- CAS
61951-99-3
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2
- Polarare Oberfläche (TPSA)
- 75,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 687
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
SolubilityInsoluble
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point607ºC at 760 mmHg
Melting Point50-55ºC
Physikochemische Eigenschaften
- Schmelzpunkt
- 254 °C · 254 °C (decomp)
- Siedepunkt
- 559.31 · 559.310±50.00 °C(Press: 760.00 Torr)(predicted)
- Dichte
- 1.27 · 1.270±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 7.916 · 7.916±0.10(predicted)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
R - Respiratory system
A - Alimentary tract and metabolism
QR - Respiratory system
QA - Alimentary tract and metabolism
Protein BindingThe presence of the C-17 in the corticosteroids is a protein binding site.
Pharmacodynamics
Tixocortol presents the characteristic of local action which reduces significantly the side effects of systemic glucocorticoids. Reports have demonstrated that gastrointestinal administration of tixocortol generates a decrease in abdominal pain, bleeding, and frequency of stools which resulted in an amelioration in the malabsorption laboratory tests. All the effects were independent of suppression of the pituitary-adrenal axis, which was shown by the absence of significant depression of cortisol. Administration of tixocortol as a nasal spray has been shown to respect nasal drainage by the ciliary beats of the pituitary mucosa. The actions of tixocortol have no effect on leukocyte count, blood glucose level, sodium urinary excretion, and immunosupressive activity on lymphocytes.
Mechanism of Action
The mechanism of action of tixocortol is similar to other corticosteroids regarding the binding sites and prostaglandin synthesis but the local properties of tixocortol are given by the immediate liver metabolism and transformation withing red blood cells. All the immediate transformations of tixocortol classified it as part of the nonsystemic steroids.
Biological Half-LifeTixocortol presents a shorter half-life than cortisol.
Metabolism/Metabolites
Tixocortol is rapidly modified within red blood cells and it is immediately metabolized by a first-pass liver metabolism. The metabolites of tixocortol are mainly represented by the formation of sulfo- and glucurono-conjugates which are later hydrolyzed from the conjugate forming neutral steroids. The metabolic transformations are the reduction of the 3-keto and delta 4 system, reduction of the C-20 carbonyl group, oxidation of the C-11 alcohol and cleavage of the side chain at C-17. The specific metabolic pathways of the C-21 thiol ester function were its transformation into methylthio, methylsulfonyl and methylsulfonyl derivatives and reductive cleavage of the C-21-S bond leading to 21-methyl structures. None of the metabolites have affinity for glucocorticoid receptors. This and the extensive metabolism explains the exclusive local activities of tixocortol.
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