Lisinopril

Bezeichnung:Lisinopril

CAS-Nr76547-98-3

Englisch Name:Lisinopril

CBNumberCB6117715

SummenformelC21H31N3O5

Molgewicht405.49

MOL-Datei76547-98-3.mol

Synonyma

Lisinopril

Lisinopril physikalisch-chemischer Eigenschaften

Schmelzpunkt	162-165 °C
Siedepunkt	666.4±55.0 °C(Predicted)
Dichte	1.251±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	H₂O: ≥10 mg/mL
Aggregatzustand	solid
pka	2.18±0.10(Predicted)
Farbe	white
BCS Class	3
CAS Datenbank	76547-98-3(CAS DataBase Reference)

Sicherheit

S-Sätze:	22-24/25
WGK Germany	3
RTECS-Nr.	TW3589990
Giftige Stoffe Daten	76547-98-3(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Lisinopril Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
Lisinopril is an angiotensin-converting enzyme (ACE) inhibitor (IC₅₀ = 1.2 nM). It reduces the formation of endothelin-1 and increases nitric oxide (NO) in human vascular endothelial cells when used at a concentration of 0.1 nM. Lisinopril inhibits the pressor response to angiotensin I in anesthetized rats and dogs (ID₅₀s = 2.3 and 6.5 μg/kg, respectively).
Originator
Acebitor 5,Biddle Sawyer,India
Verwenden
Labeled Lisinopril, intended for use as an internal standard for the quantification fo Lisinopril by GC- or LC-mass spectrometry.
Verwenden
Lisinopril is an antihypertensive medication.
Definition
ChEBI: Lisinopril is a dipeptide. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It contains a L-prolino group and a L-lysine residue.
Manufacturing Process
2-Oxo-4-phenylbutyric acid and t-BOC-L-lysyl-L-proline are condensed in the presence of sodium cyanoborohydride. Essentially all of the t-BOC protecting group is cleaved when the product is absorbed on strong acid ion exchange resin. The crude N-(1-carboxy-3-phenylpropyl)-L-lysyl-L-proline is eluted from the resin with 10% ammonia, freeze dried, and purified by gel filtration chromatography (LH-20). A minute peak for t-BOC protons in the NMR spectrum disappears when the product is treated with ethyl acetate that is 4 N in hydrogen chloride gas. The NMR spectrum of the resulting HCl salt of the product is consistent with structure. The mass spectrum shows a molecular ion at 693 m/e for the tetrasilylated species. Chromatography on XAD-2 resin using 3.5% acetonitrile in 0.1 molar ammonium hydroxide affords N-α-((1S)- 1-carboxy-3-phenylpropyl)-L-lysyl-L-proline. The last peptide can be produced if 2-oxo-4-phenylbutyric acid and N-t-Boc-L-lysyl-L-proline are condensed in the presence of sodium cyanoborohydride. The product is absorbed on strong acid ion exchange resin, and eluted with 2% pyridine in water. Product-rich cuts are stripped to a glass and treated with 4 N HCl in ethylacetate to remove the t-Boc protecting group. The resulting hydrochloride salt is converted to the free base by absorbing on strong acid ion exchange resin and eluting with 2% pyridine in water. Freeze drying of product-rich cuts affords N-α-(1-carboxy-3-phenylpropyl)-L-lysyl-L-proline as a white fluffy solid. The NMR spectrum is consistent with structure. The mass spectrum shows a molecular ion at 549 for the disilylated species. Chromatography affords the desired isomer.
Trademarks
Prinivil (Merck); Zestril (AstraZeneca).
Therapeutic Function
Antihypertensive

Lisinopril Upstream-Materialien And Downstream Produkte

Lisinopril Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

76547-98-3, Lisinopril Verwandte Suche:

Send Inquriy