475086-01-2CC(C)N(CCCCOCC(=O)NS(C)(=O)=O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1QXWZQTURMXZVHJ-UHFFFAOYSA-NSelexipag 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.
475086-01-2Breast 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
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
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.
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 Rank (DILIrank 2.0)
Selexipag
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
B - Blood and blood forming organs
QB - Blood and blood forming organs
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.
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.
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.
Wird geladen…
DTXSID301027959CHEMBL238804CHEBI:908445EXC0E384L
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
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.
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.
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.
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.