Fosinoprilat
Grundinformationen
- CAS
95399-71-6- Standard-SMILES
O=C(O)[C@@H]1C[C@@H](C2CCCCC2)CN1C(=O)CP(=O)(O)CCCCc1ccccc1- InChIKey
WOIWWYDXDVSWAZ-RTWAWAEBSA-N- Summenformel
- C23H34NO5P
- Durchschnittliche Molmasse
- 435,5 g/mol
- Monoisotopische Masse
- 435,21746018
Überblick
Fosinoprilat is a phosphinic acid-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. An inhibitor of angiotensin converting enzyme (ACE), it is used as the phosphinate ester pro-drug fosinopril for treatment of hypertension and chronic heart failure. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor and an antihypertensive agent. It is a member of phosphinic acids and a L-proline derivative.
Namen und Bezeichner
- Bevorzugter Name
- Fosinoprilat
- IUPAC
- (2S,4S)-4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
- Englischer Name
- FOSINOPRILAT
- Summenformel
- C23H34NO5P
- Molmasse
- 435.49
Namen und Synonyme
Fosinoprilat95399-71-6fosfenoprilFosinopril diacidFosinoprilic acidFosinoprilatumSQ-27519SQ 27,519PU6BA2D2MD(4S)-4-Cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphinyl)acetyl)-L-prolineS312EY6ZT8SO-27519
Weitere Namen anzeigen
FospenoprilForsinoprilatFosinoprilat-D5fosinoprilicacidFosinopril ImpuritySQ 27519 Disodium Salt
CHEBI:116962DTXSID80869253L-Proline, 4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphinyl)acetyl)-, trans-(4S)-4-cyclohexyl-1-{[hydroxy(4-phenylbutyl)phosphoryl]acetyl}-L-proline(4S)-4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphoryl)acetyl)-L-proline(2S,4S)-4-cyclohexyl-1-(2-(hydroxy-(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylic acid(2S,4S)-4-cyclohexyl-1-[2-(hydroxy-(4-phenylbutyl)phosphoryl)acetyl]pyrrolidine-2-carboxylic acidRefChem:57081
Datenbank-Bezeichner
- CAS
95399-71-6- PubChem CID
- 62956
- DTXSID
DTXSID80869253
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,8
- Polarare Oberfläche (TPSA)
- 94,9 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 9
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 627
Experimentelle und physikochemische Eigenschaften
LogP4.08
Physikochemische Eigenschaften
- Schmelzpunkt
- 3000 C · >3000C
- Siedepunkt
- 728.9 · 728.9±60.0 °C(Predicted)
- Dichte
- 1.238 · 1.238±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- Löslichkeit
- Methanol (Slightly), Water (Slightly)
- pka
- 2.75 · 2.75±0.50(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Stabilität
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- WOIWWYDXDVSWAZ-RTWAWAEBSA-N
- SMILES
- [P](=O)(O)(CCCCc3ccccc3)CC(=O)N1[C@@H](C[C@H](C1)C2CCCCC2)C(=O)O
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
H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory InformationL-Proline, 4-cyclohexyl-1-hydroxy(4-phenylbutyl)phosphinylacetyl-, (4S)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesRepr. 1A (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2933995300
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Repr. 1A
Chemie und Industrie
Pharmakologische Informationen
FDA Pharmacological Classification
S312EY6ZT8
FOSINOPRILAT
Established Pharmacologic Class [EPC] - Angiotensin Converting Enzyme Inhibitor
Mechanisms of Action [MoA] - Angiotensin-converting Enzyme Inhibitors
Fosinoprilat is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of fosinoprilat is as an Angiotensin-converting Enzyme Inhibitor.
MeSH Pharmacological Classification
A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility.
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Anwendungen
VerwendenFosinoprilat (Fosinopril EP Impurity A) is a metabolite of Fosinopril (F727800), a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor.
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