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Selexipag

HCID 9913767
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
475086-01-2
Standard-SMILES
CC(C)N(CCCCOCC(=O)NS(C)(=O)=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1
InChIKey
QXWZQTURMXZVHJ-UHFFFAOYSA-N
Summenformel
C26H32N4O4S
Durchschnittliche Molmasse
496,6 g/mol
Monoisotopische Masse
496,21442669

Überblick

Selexipag is a member of the class of pyrazines that is N-(methanesulfonyl)-2-{4-[(propan-2-yl)(pyrazin-2-yl)amino]butoxy}acetamide carrying two additional phenyl substituents at positions 5 and 6 on the pyrazine ring. An orphan drug used for the treatment of pulmonary arterial hypertension. It is a prodrug for ACT-333679 (the free carboxylic acid). It has a role as a vasodilator agent, a prodrug, a platelet aggregation inhibitor, an orphan drug and a prostacyclin receptor agonist. It is an ether, a monocarboxylic acid amide, an aromatic amine, a member of pyrazines, a tertiary amino compound and a N-sulfonylcarboxamide. It is functionally related to an ACT-333679.

Namen und Bezeichner

Bevorzugter Name
Selexipag
IUPAC
2-[4-[(5,6-diphenylpyrazin-2-yl)-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
Englischer Name
Selexipag
Summenformel
C26H32N4O4S
Molmasse
496.62

Namen und Synonyme

Selexipag475086-01-2NS-304UptraviACT-293987NS 304ACT 2939875EXC0E384L2-[4-[(5,6-Diphenyl-2-pyrazinyl)(1-methylethyl)amino]butoxy]-N-(methylsulfonyl)acetamideACT293987CHEBI:90844DTXSID301027959
Weitere Namen anzeigen
SlipperelexipagSelxxipagSelixapagSelexipag APIThe company westNS-304(Selexipag)
2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-N-(methanesulfonyl)acetamide2-{4-[(5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino]butoxy}-N-methanesulfonylacetamide2-(4-((5,6-Diphenylpyrazin-2-yl)(propan-2-yl)amino)butoxy}-n-(methanesulfonyl)acetamide2-(4-((5,6-DIPHENYLPYRAZIN-2-YL)(PROPAN-2-YL)AMINO)BUTOXY)-N-(METHANESULFONYL)ACETAMIDEselexipagum2-(4-((5,6-di(phenyl)pyrazin-2-yl)-propan-2-ylamino)butoxy)-N-methylsulfonylacetamide2-(4-((5,6-Diphenyl-2-pyrazinyl)(1-methylethyl)amino)butoxy)-N-(methylsulfonyl)acetamide2-(4-((5,6-diphenylpyrazin-2-yl)(propan-2-yl)amino)butoxy)-N-methanesulfonylacetamide

Datenbank-Bezeichner

CAS
475086-01-2
PubChem CID
9913767

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
110 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
12
Schwere Atome
35
Formalladung
0
Komplexität
730

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 4 Einträge

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Cardiovascular Agents; Vasodilator Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
134 · 134-138°C
Dichte
1.21 · 1.210±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C Freezer
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
pka
3.82 · 3.82±0.40(Predicted)
Aggregatzustand
Solid
Farbe
Pale Yellow
InChIKey
QXWZQTURMXZVHJ-UHFFFAOYSA-N
SMILES
C(NS(C)(=O)=O)(=O)COCCCCN(C1=NC(C2=CC=CC=C2)=C(C2=CC=CC=C2)N=C1)C(C)C

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

H302 (60%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (60%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Selexipag is associated with a low rate of serum aminotransferase elevations (0% to 3%) that in clinical trials was similar to the rate among placebo recipients. These elevations were usually mild (rarely above 3 times ULN), transient and not associated with symptoms. There were no cases of serum enzyme elevations with jaundice in these preregistration clinical trials. Since licensure and more wide scale use, there have been no published reports of clinically apparent liver injury with jaundice associated with selexipag, but it has had limited general use.

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Selexipag

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

B - Blood and blood forming organs

QB - Blood and blood forming organs

Protein BindingBoth selexipag and its active metabolite are highly protein bound, approximately 99%.
Pharmacodynamics · 1 Eintrag

At the maximum tolerated dose of 1600 mcg twice per day, selexipag was not found to prolong the QT interval to a clinically relevant extent. Both selexipag and its metabolite caused concentration-dependent inhibition of platelet aggregation in vitro with IC50 of 5.5 µM and 0.21 µM, respectively. However, at clinically relevant concentrations, there was no effect on platelet aggregation test parameters following multiple dose administration of selexipag in healthy patients.

Mechanism of Action · 1 Eintrag

Selexipag is a selective prostacyclin (IP, also called PGI2) receptor agonist. The key features of pulmonary arterial hypertension include a decrease in prostacyclin and prostacyclin synthase (enzyme that helps produce prostacyclin) in the lung. Prostacyclin is a potent vasodilator with anti-proliferative, anti-inflammatory, and anti-thrombotic effects; therefore, there is strong rationale for treatment with IP receptor agonists. Selexipag is chemically distinct as it is not PGI2 or a PGI2 analogue and has high selectivity for the IP receptor. It is metabolized by carboxylesterase 1 to yield an active metabolite (ACT-333679) that is approximately 37 times more potent than selexipag. Both selexipag and its metabolite are selective for the IP receptor over other prostanoid receptors.

Biological Half-LifeSelexipag's terminal half life is 0.8-2.5 hours. The active metabolite's terminal half life is 6.2-13.5 hours.
Metabolism/Metabolites · 1 Eintrag

Selexipag yields its active metabolite by hydrolysis of the acylsulfonamide by the enzyme hepatic carboxylesterase 1. Oxidative metabolism catalyzed by CYP3A4 and CYP2C8 results in hydroxylated and dealkylated products. UGT1A3 and UGT2B7 are involved in the glucuronidation of the active metabolite. Other than active metabolite, other metabolites in circulation do not exceed 3% of the total drug-related material.

Zugehörige Reaktionen

2
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 941595
HRID 941595als ProduktValidation data from https://doi.org/10.1039/C8SC04228D
Reaktionsgleichung von HRID 1271310
HRID 1271310als Produktuspto-grants-2007_04

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID
DTXSID301027959
ChEMBL
CHEMBL238804
ChEBI
CHEBI:90844
UNII
5EXC0E384L
EC Number
809-991-1
Nikkaji
J2.120.977E
wgk
WGK 3
Speicherklasse
11 - Combustible Solids
FDA Pharmacological Classification · 6 Einträge

5EXC0E384L

SELEXIPAG

Established Pharmacologic Class [EPC] - Prostacyclin Receptor Agonist

Mechanisms of Action [MoA] - Prostacyclin Receptor Agonists

Selexipag is a Prostacyclin Receptor Agonist. The mechanism of action of selexipag is as a Prostacyclin Receptor Agonist.

SELEXIPAG

MeSH Pharmacological Classification · 1 Eintrag

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.

Absorption, Distribution and Excretion · 3 Einträge

After oral administration, maximum concentrations of selexipag and its metabolite were observed to be reached at 1-3 and 3-4 hours, respectively. Absorption was impaired in the presence of food, resulting in delayed time to maximum concentration as well as ~30% lower peak plasma concentration. However, exposure was not found to be significantly affected by food.

93% in feces, 12% in urine.

On average, 35 L/hour.

Anwendungen · 2 Einträge

BeschreibungSelexipag and its active metabolite, the corresponding carboxylic acid, are nonprostanoid prostaglandin I2 (PGI-2) receptor agonists. The N-methylsulfonamide within selexipag is hydrolyzed to the corresponding carboxylic acid in vivo by hepatic microsomes at a rate which provides a slow-release pharmacological effect. The compound was originally discovered by Nippon Shinyaki and later licensed to Actelion for development. The drug was approved in 2015 and first launched for the oral treatment of pulmonary arterial hypertension (PAH) in the U.S. in 2016 to delay disease progression and reduce the risk of hospitalization.

VerwendenSelexipag is an orally available, highly selective, long-acting prostacyclin (IP) receptor agonist prodrug. It is a potential drug for the treatment of various vascular disorders such as pulmonary arterial hypertension and arteriosclerosis obliterans.

Anbieter106 Anbieter

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Selexipag is a member of the class of pyrazines that is N-(methanesulfonyl)-2-{4-[(propan-2-yl)(pyrazin-2-yl)amino]butoxy}acetamide carrying two additional phenyl substituents at positions 5 and 6 on the pyrazine ring. An orphan drug used for the treatment of pulmonary arterial hypertension. It is a prodrug for ACT-333679 (the free carboxylic acid). It has a role as an orphan drug, a prostacyclin receptor agonist, a platelet aggregation inhibitor, a vasodilator agent and a prodrug. It is a monocarboxylic acid amide, an ether, a member of pyrazines, an aromatic amine, a tertiary amino compound and a N-sulfonylcarboxamide. It is functionally related to an ACT-333679.