| Identification | More | [Name]
Lisinopril | [CAS]
76547-98-3 | [Synonyms]
ACERBON
ALAPRIL
CARACE
CORIC
LISINOPRIL
LISINOPRIL DIHYDRATE
MK-521
n-{n-[(s)-1-carboxy-3-phenylpropyl]-l-lysyl}-l-proline
NOVATEC
PRINIL
PRINIVIL
(S)-1-(N2-(1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-L-PROLINE, DIHYDRATE
(S)-1-[(S)-6-AMINO-2-((S)-1-CARBOXY-3-PHENYL-PROPYLAMINO)-HEXANOYL]-PYRROLIDINE-2-CARBOXYLIC ACID
TENSOPRIL
VIVATEC
ZESTRIL
(s)-1-(n(sup2)-(1-carboxy-3-phenylpropyl)-l-lysyl)-l-proline
lysinopril
mk0521
mk-0521 | [EINECS(EC#)]
278-488-1 | [Molecular Formula]
C21H31N3O5 | [MDL Number]
MFCD00214086 | [Molecular Weight]
405.49 | [MOL File]
76547-98-3.mol |
| Hazard Information | Back Directory | [Description]
Lisinopril is an angiotensin-converting enzyme (ACE) inhibitor (IC50 = 1.2 nM).1 It reduces the formation of endothelin-1 (Item No. 24127) and increases nitric oxide (NO) in human vascular endothelial cells when used at a concentration of 0.1 nM.2 Lisinopril inhibits the pressor response to angiotensin I in anesthetized rats and dogs (ID50s = 2.3 and 6.5 μg/kg, respectively).1 | [Originator]
Acebitor 5,Biddle Sawyer,India | [Uses]
Labeled Lisinopril, intended for use as an internal standard for the quantification fo Lisinopril by GC- or LC-mass spectrometry. | [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. | [Brand name]
Prinivil (Merck); Zestril (AstraZeneca). | [Therapeutic Function]
Antihypertensive |
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