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Lixisenatide

HCID 90472060
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Grundinformationen

CAS
320367-13-3
Standard-SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@@H](N)Cc1c[nH]cn1)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(N)=O
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InChIKey
XVVOERDUTLJJHN-JXBMKTOPNA-N
Summenformel
C215H347N61O65S
Durchschnittliche Molmasse
4.858 g/mol
Monoisotopische Masse
4.855,5443218

Überblick

Lixisenatide is a forty-four membered polypeptide consisting of L-His, Gly, L-Glu, Gly, L-Thr, L-Phe, L-Thr, L-Ser, L-Asp, L-Leu, L-Ser, L-Lys, L-Gln, L-Met, L-Glu, L-Glu, L-Glu, L-Ala, L-Val, L-Arg, L-Leu, L-Phe, L-Ile, L-Glu, L-Trp, L-Leu, L-Lys, L-Asn, Gly, Gly, LPro, L-Ser, L-Ser, Gly, L-Ala, L-Pro, L-Pro, L-Ser, L-Lys, L-Lys, L-Lys, L-Lys, L-Lys, and L-Lys-NH2 residues joined in sequence. Used as an adjunct to diet and exercise for the treatment of adults with type II diabetes. It has a role as a hypoglycemic agent, a neuroprotective agent and a glucagon-like peptide-1 receptor agonist. It is a peptidyl amide and a polypeptide.

Namen und Bezeichner

Bevorzugter Name
Lixisenatide
IUPAC
(4S)-5-[[2-[[(2S,3R)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-4-amino-1-[[2-[[2-[(2S)-2-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[(2S)-2-[(2S)-2-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-2-oxoethyl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-4-[[2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]acetyl]amino]-5-oxopentanoic acid
Englischer Name
Lixisenatide
Summenformel
C215H347N61O65S
Molmasse
4858.53

Namen und Synonyme

LixisenatideAdlyxinLyxumiaZP10A peptide320367-13-3ZP 10AVE0010AQVE-10010AVE 0010lixisenatidalixisenatidumAVE 010
Weitere Namen anzeigen
ixisenatideLixisenatide GLP-1Lixisenatide, >98%Lixisenatide AcetateLixisenatide USP/EP/BPLixisenatide|Lixisenatide Acetate
AVE-010ZP-10AVE-0010Des-38-proline-exendine-4 (Heloderma suspectum)-(1-39)-peptidylpenta-L-lysyl-L-lysinamideCHEBI:8566274O62BB01UDesPro38Exendin-4(1-39)-Lys6-NH2RefChem:391

Datenbank-Bezeichner

CAS
320367-13-3
PubChem CID
90472060
ChEMBL
CHEMBL2108336
ChEBI
CHEBI:85662
EC Number
685-146-9

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-30,8
Polarare Oberfläche (TPSA)
2.090 Ų
H-Brücken-Donoren
70
H-Brücken-Akzeptoren
77
Frei drehbare Bindungen
170
Schwere Atome
342
Formalladung
0
Komplexität
11.800

Experimentelle und physikochemische Eigenschaften

BiologicsBiologic product (Adlyxin) -> FDA Purple Book
Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Hypoglycemic Agents; Incretins; Glucagon-Like Peptide-1 Agonists; GLP-1 Agonists

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

storage temp.
-20 °C · Store at -20°C
Löslichkeit
103 · Water:103.0(Max Conc. mg/mL);21.2(Max Conc. mM)
Aggregatzustand
Solid
Farbe
White to pink
InChIKey
XVVOERDUTLJJHN-JXBMKTOPNA-N
CAS Datenbank
320367 · 320367-13-3

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 · 4 Einträge

Danger

H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P203, P264+P265, P280, P305+P354+P338, P317, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesEye Dam. 1 (100%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

In large clinical trials, serum enzyme elevations were no more common with lixisenatide therapy than with placebo or comparator agents. In pooled safety analyses of more than 5000 patients, ALT elevations above 3 times the upper limit of normal occurred in 0.6% of both lixisenatide and placebo groups and no instances of treatment related clinically apparent liver injury were reported. Since licensure, there have been no published case reports of hepatotoxicity due to lixisenatide and the product label does not list liver injury as an adverse event. Thus, liver injury due to lixisenatide, as with other GLP-1 analogues, must be rare, if it occurs at all.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H318

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein BindingLixisenatide is approximately 55% bound to human plasma proteins.
Pharmacodynamics · 1 Eintrag

Lixisenatide acts as an agonist at the GLP-1 receptor. In the pancreas, this agonism results in increased glucose-stimulated insulin exocytosis by beta islet cells. This produces a reduction in blood glucose due to increased glucose uptake by tissues. GLP-1 receptor activation in the GI tract results in delayed gastric emptying which is thought to mediate the effects of lixisenatide on postprandial blood glucose.

Mechanism of Action · 1 Eintrag

The activation of the GLP-1 receptor by lixisenatide results in the activation of adenylyl cyclase. This increases the concentration of cyclic adenosine monophosphate in the cell leading to the activation of protein kinase A (PKA) as well as Epac1 and Epac2. PKA, Epac1, and Epac2 are involved the in release of Ca2+ from the endoplasmic reticulum which is known as the "amplification" pathway which increases insulin release when the triggering pathway is activated. By activating this amplification pathway lixisenatide increases glucose stimulated insulin secretion.

Biological Half-LifeFollowing the administration of multiple doses in patients with type II diabetes mellitus, the mean terminal half-life of lixisenatide was approximately 3 hours.
Metabolism/MetabolitesLixisenatide is likely catabolized via non-specific proteolytic degradation.
FDA Pharmacological Classification · 6 Einträge

74O62BB01U

LIXISENATIDE

Established Pharmacologic Class [EPC] - GLP-1 Receptor Agonist

Chemical Structure [CS] - Glucagon-Like Peptide 1

Mechanisms of Action [MoA] - Glucagon-like Peptide-1 (GLP-1) Agonists

Lixisenatide is a GLP-1 Receptor Agonist. The mechanism of action of lixisenatide is as a Glucagon-like Peptide-1 (GLP-1) Agonist.

Absorption, Distribution and Excretion · 4 Einträge

Following subcutaneous administration, the median Tmax of lixisenatide ranged from 1-3.5 hours, with no clinically relevant differences in the rate of absorption noted between possible injection sites (i.e. thigh, abdomen, or arm).

Lixisenatide is presumably eliminated via glomerular filtration and proteolytic degradation.

The apparent volume of distribution following subcutaneous administration is approximately 100 L.

The mean apparent clearance of lixisenatide is approximately 35 L/h.

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