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QuickView for Bosentan (compound)

Name: bosentan
PubChem Compound ID: 104865
Molecular formula: C27H29N5O6S
Molecular weight: 551.615 g/mol
Ro-47-0203/039; Tracleer; Bosentan; Ro-47-0203/029; Benzenesulfonamide, 4-(1,1-dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)(2,2'-bipyrimidin)-4-yl)-; Ro-47-0203; 147536-97-8; p-tert-Butyl-N-(6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide; Ro 47-0203; 174227-18-0.
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Name: bosentan
Name (isomeric): DB00559
Drug Type: small molecule
Bosentan hydrate
Brand: Tracleer
Category: Antihypertensive Agents
CAS number: 147536-97-8
Indication: Used in the treatment of pulmonary arterial hypertension (PAH), to improve exercise ability and to decrease the rate of clinical worsening (in patients with WHO Class III or IV symptoms).
Pharmacology: Bosentan belongs to a class of drugs known as endothelin receptor antagonists (ERAs). Patients with PAH have elevated levels of endothelin, a potent blood vessel constrictor, in their plasma and lung tissue. Bosentan blocks the binding of endothelin to its receptors, thereby negating endothelin's deleterious effects.
Mechanism of Action:
Endothelin-1 (ET-1) is a neurohormone, the effects of which are mediated by binding to ETA and ETB receptors in the endothelium and vascular smooth muscle. ET-1 concentrations are elevated in plasma and lung tissue of patients with pulmonary arterial hypertension, suggesting a pathogenic role for ET-1 in this disease. Bosentan...
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Absorption: Absolute bioavailability is approximately 50% and food does not affect absorption.
Protein binding: Greater than 98% to plasma proteins, mainly albumin.
Biotransformation: Bosentan is metabolized in the liver by the cytochrome P450 enzymes CYP2C9 and CYP3A4 (and possibly CYP2C19), producing three metabolites, one of which, Ro 48-5033, is pharmacologically active and may contribute 10 to 20% to the total activity of the parent compound.
Route of elimination: Bosentan is eliminated by biliary excretion following metabolism in the liver.
Half Life: Terminal elimination half-life is about 5 hours in healthy adult subjects.
Clearance: 4 L/h [patients with pulmonary arterial hypertension]
Toxicity: Bosentan has been given as a single dose of up to 2400 mg in normal volunteers, or up to 2000 mg/day for 2 months in patients, without any major clinical consequences. The most common side effect was headache of mild to moderate intensity. In the cyclosporine A interaction study, in which doses of 500 and 1000 mg b.i.d. of bosentan were given concomitantly with cyclosporine A, trough plasma concentrations of bosentan increased 30-fold, resulting in severe headache, nausea, and vomiting, but no serious adverse events. Mild decreases in blood pressure and increases in heart rate were observed. There is no specific experience of overdosage with bosentan beyond the doses described above. Massive overdosage may result in pronounced hypotension requiring active cardiovascular support.
Affected organisms: Humans and other mammals
Food interaction:
Take without regard to meals.
Drug interaction:
TramadolBosentan may decrease the effect of Tramadol by increasing Tramadol metabolism and clearance.
DicumarolBosentan may decrease the anticoagulant effect of dicumarol by increasing its metabolism.
MestranolDecreases the effect of contraceptive
NorethindroneBosentan may decrease the contraceptive effect of norethindrone. Hormonal contraception should not be relied on alone during concomitant therapy with bosentan.
CyclosporineCyclosporine may increase the effect and toxicity of bosentan.
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