Iloprost
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Grundinformationen
- CAS
78919-13-8- Standard-SMILES
CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCC(=O)O)C[C@H]2C[C@H]1O- InChIKey
HIFJCPQKFCZDDL-ACWOEMLNSA-N- Summenformel
- C22H32O4
- Durchschnittliche Molmasse
- 360,5 g/mol
- Monoisotopische Masse
- 360,2300595
Überblick
Iloprost is a carbobicyclic compound that is prostaglandin I2 in which the endocyclic oxygen is replaced by a methylene group and in which the (1E,3S)-3-hydroxyoct-1-en-1-yl side chain is replaced by a (3R)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl group. A synthetic analogue of prostacyclin, it is used as the trometamol salt (generally by intravenous infusion) for the treatment of peripheral vascular disease and pulmonary hypertension. It has a role as a vasodilator agent and a platelet aggregation inhibitor. It is a monocarboxylic acid, a secondary alcohol and a carbobicyclic compound.
Namen und Bezeichner
- Bevorzugter Name
- Iloprost
- IUPAC
- (5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
Namen und Synonyme
ILOPROSTCiloprost78919-13-8VentavisEndoprostIlomedinAurlumynIloprostumZK-36374DTXSID2041046JED5K35YGLZK 36374
Weitere Namen anzeigen
ZK 00036374CHEBI:63916ZK-00036374DTXCID001333799(5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]hexahydropentalen-2(1H)-ylidene]pentanoic acidPentanoic acid, 5-(hexahydro-5-hydroxy-4-(3-hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)-pentalenylidene)-(E)-(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-((E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl)-delta(sup 2(1H),delta)-pentalenevaleric acidPENTANOIC ACID, 5-((3AS,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-((1E,3S)-3-HYDROXY-4-METHYL-1-OCTEN-6-YNYL)-2(1H)-PENTALENYLIDENE)-, (5E)-
Datenbank-Bezeichner
- CAS
78919-13-8- PubChem CID
- 5311181
- DTXSID
DTXSID2041046- ChEMBL
CHEMBL494- ChEBI
CHEBI:63916- UNII
- JED5K35YGL
- EC Number
- 636-055-8
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2,8
- Polarare Oberfläche (TPSA)
- 77,8 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 606
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Antihypertensives
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Cardiovascular Agents; Prostaglandins, Synthetic; Vasodilator Agents
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Pharmaceuticals
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301 (98.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (98.5%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Iloprost
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemie und Industrie
Pharmakologische Informationen
ATC Code
B01AC11
B - Blood and blood forming organs
QB - Blood and blood forming organs
Protein BindingIloprost is approximately 60% protein-bound, mainly to albumin, and this ratio is concentration-independent in the range of 30 to 3000 pg/mL.
Pharmacodynamics
Iloprost is a synthetic analogue of prostacyclin PGI2 that dilates systemic and pulmonary arterial vascular beds. There are two diastereoisomers of iloprost and the 4S isomer is reported to exhibit a higher potency in dilating blood vessels compared to the 4R isomer. In patients with primary pulmonary hypertension, iloprost decreased pulmonary vascular resistance and pulmonary artery pressure. Iloprost was shown to inhibit platelet aggregation, but whether this effect contributes to its vasodilatory action has not been elucidated. Iloprost is reported to attenuate ischemia-induced tissue injury. When administered intravenously in patients with peripheral vascular conditions such as critical leg ischemia and delayed amputation, iloprost was shown to promote cytoprotection. In isolated animal heart preparations and in intact animals with ischemia-reperfusion injury, preserved myocardial function was observed following iloprost administraion.
Mechanism of Action
In pulmonary arterial hypertension, endothelial vasoactive mediators such as nitric oxide and prostacyclin are released to induce vasoconstriction. Iloprost mimics the biological actions of prostacyclin, a short-lived prostanoid and potent vasodilator mainly produced in the vascular endothelium. The exact mechanism of iloprost in cytoprotection has not been fully elucidated; however, it is proposed that iloprost decreases catecholamine outflow from sympathetic nerve terminals, preserves mitochondrial function, and reduces oxidative stress. Decreased neutrophil accumulation and membrane stabilization have also been suggested.
Biological Half-LifeThe half-life of iloprost is 20 to 30 minutes.
Metabolism/Metabolites
Zugehörige Reaktionen
1
Notizen zur Verbindung
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