Perindopril

HCID 107807

Grundinformationen

CAS
107133-36-8
Standard-SMILES
CCC[C@H](N[C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21)C(=O)OCC
InChIKey
IPVQLZZIHOAWMC-QXKUPLGCSA-N
Summenformel
C19H32N2O5
Durchschnittliche Molmasse
368,5 g/mol
Monoisotopische Masse
368,23112212

Überblick

Perindopril is an alpha-amino acid ester that is the ethyl ester of N-{(2S)-1-[(2S,3aS,7aS)-2-carboxyoctahydro-1H-indol-1-yl]-1-oxopropan-2-yl}-L-norvaline. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor and an antihypertensive agent. It is an ethyl ester, an organic heterobicyclic compound, a dicarboxylic acid monoester and an alpha-amino acid ester. It is a conjugate acid of a perindopril(1-).

Namen und Bezeichner

Bevorzugter Name
Perindopril
IUPAC
(2S,3aS,7aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid
Englischer Name
Perindopril erbumine
Summenformel
C23H43N3O5
Molmasse
441.61

Namen und Synonyme

PERINDOPRIL82834-16-0PerindoprilumMcN-A-2833S-9490DTXSID6023440Y5GMK36KGYCHEBI:8024DTXCID303440S 9490(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acid(2S,3aS,7aS)-1-((S)-N-((S)-1-Carboxybutyl)alanyl)hexahydro-2-indolinecarboxylic acid, 1-ethyl ester
Weitere Namen anzeigen
Aceonprindopril APIPerindopril ErbuMine (Aceon)Perindopril t-ButylaMinePerindopril tert-butylamine saltPerindopril for stereochemical purity CRSCoversuMPrestariuMPerindorilPerinodopril
(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid1H-Indole-2-carboxylic acid, 1-(2-((1-(ethoxycarbonyl)butyl)amino)-1-oxopropyl)octahydro-, (2S-(1(R*(R*)),2alpha,3abeta,7abeta))-S9490Pirindopril(2S,3aS,7aS)-1-((2S)-2-(((2S)-1-ethoxy-1-oxopentan-2-yl)amino)propanoyl)-octahydro-1H-indole-2-carboxylic acid(2S,3aS,7aS)-1-((2S)-2-(((2S)-1-ethoxy-1-oxopentan-2-yl)amino)propanoyl)octahydro-1H-indole-2-carboxylic acid(2S,3aS,7aS)-1-[(S)-N-[(S)-1-Carboxybutyl]alanyl]hexahydro-2-indolinecarboxylic acid, 1-ethyl esterErbumine, Perindopril

Datenbank-Bezeichner

CAS
107133-36-8、82834-16-0
PubChem CID
107807
DTXSID
DTXSID6023440
ChEMBL
CHEMBL1581
ChEBI
CHEBI:8024
UNII
Y5GMK36KGY
EC Number
617-394-0
Nikkaji
J23.744B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,9
Polarare Oberfläche (TPSA)
95,9 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
9
Schwere Atome
26

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antihypertensives

LogP2.6
Solubility1.22e+00 g/L
Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Angiotensin-Converting Enzyme Inhibitors; ACE Inhibitors

Pharmaceuticals

Physical DescriptionSolid
Collision Cross Section189.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1044198]

Physikochemische Eigenschaften

Schmelzpunkt
126 · 126-128°C
storage temp.
2 · 2-8°C
Löslichkeit
2 O: · H2O: soluble10mg/mL, clear
Aggregatzustand
powder
Farbe
White
Major Application
pharmaceutical (small molecule)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P260, P261, P264+P265, P271, P280, P304+P340, P305+P351+P338, P318, P319, P337+P317, P403+P233, 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

Hazard Classes and CategoriesEye Irrit. 2 (100%)

Toxikologische Informationen

HepatotoxicityPerindopril, like other ACE inhibitors, has been associated with a low rate of serum aminotransferase elevations (
Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

perindopril

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
hs_code
2933999552
RTECS-Nr.
NL5999600
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

C09AA04

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingPerindoprilat, 10-20% bound to plasma proteins
Pharmacodynamics · 1 Eintrag

Perindopril is a nonsulfhydryl prodrug that is metabolized via first pass effect (62%) and systemic hydrolysis (38%) to perindoprilat, its active metabolite, following oral administration. Perindoprilat lowers blood pressure by antagonizing the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain the effects of perindoprilat by causing increased vasodilation and decreased blood pressure.

Mechanism of Action · 1 Eintrag

There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Perindoprilat, the active metabolite of perindopril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Perindopril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.

Biological Half-LifePerindopril, 1.2 hours; Peridoprilat, 30-120 hours. The long half life of peridoprilat is due to its slow dissociation from ACE binding sites.
Metabolism/Metabolites · 2 Einträge

Extensively metabolized, with only 4-12% of the dose recovered in urine following oral administration. Six metabolites have been identified: perindoprilat, perindopril glucuronide, perindoprilat glucuronide, a perindopril lactam, and two perindoprilat lactams. Only perindoprilat is pharmacologically active. Peridoprilat and perindoprilat glucuronide are the two main circulating metabolites.

Perindopril has known human metabolites that include Perindoprilat glucuronide.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationPharmaceuticals

Anwendungen

VerwendenAn angiotensin-converting enzyme (ACE) inhibitor. Antihypertensive.

Anbieter101 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海拓克化学科技有限公司+86-021-69895597 13776836200 +86-13776836200 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]

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