Peringatan Keamanan

At high doses, macitentan may produce headache, nausea, and vomiting.L39105 In case of overdose standard supportive measures are recommended. Hemodialysis is not expected to contribute significantly to macitentan clearance due to its high degree of plasma protein binding.

Macitentan

DB08932

small molecule approved

Deskripsi

Macitentan is a dual endothelin receptor antagonist used in the treatment of pulmonary arterial hypertension (PAH).L35890 It was first approved by the FDA in 2013. Macitentan differs from its predecessor bosentan in part due to its lower risk of hepatotoxicity.

A combination product (Opsynvi) comprising macitentan and tadalafil was approved in Canada in October 2021 for the treatment of PAH.L39105 It was subsequently approved by the FDA in March 2024.L50622

Struktur Molekul 2D

Berat 588.273
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) The half-life of elimination of macitentan is 16 hours.[L39105, A174082] The half-life of elimination of the active metabolite is 40-66h.
Volume Distribusi Macitentan has an apparent volume of distribution of 40-50L.[L39105, A174082]
Klirens (Clearance) Clearance data was not found.

Absorpsi

Macitentan has a median Tmax of 8h although some studies have found up to 30h at higher doses.L39105, A174082 Although the bioavailability has not been experimentally determined, pharmacokinetic modeling has estimated it at 74%.A174082 Food has not been found to have a significant effect on absorption.

Metabolisme

Macitentan undergoes oxidative depropylation of the sulfonamide moiety via CYP3A4, 2C8, 2C9, and 2C19 to form the active metabolite M6.A174082 The ethylene glycol moiety undergoes oxidative cleavage via CYP2C9 to the alcohol metabolite M4. M4 is oxidized to its corresponding acid, M5, then hydrolyzed to the metabolite termed m/z 324. Oxidative depropylation of a distal carbon atom via CYP2C8, 2C9, and 2C19 forms M7. Hydrolysis of both macitentan and M5 produces M3. Finally M5 may be further metabolized via hydrolysis and hydroxylation to M2 or via glucuronidation to a glucuronide metabolite, M1.

Rute Eliminasi

Eliminated 50% through urine and 24% through feces.L39105, A174082 Of the 50% excreted through the urine, none of the recovered dose was in the form of the parent drug nor the active metabolite.

Interaksi Makanan

1 Data
  • 1. Take with or without food.

Interaksi Obat

1206 Data
Alfuzosin Alfuzosin may increase the hypotensive activities of Macitentan.
Amifostine Macitentan may increase the hypotensive activities of Amifostine.
Diazoxide Diazoxide may increase the hypotensive activities of Macitentan.
Methylphenidate Methylphenidate may decrease the antihypertensive activities of Macitentan.
Dexmethylphenidate Dexmethylphenidate may decrease the antihypertensive activities of Macitentan.
Obinutuzumab Macitentan may increase the hypotensive activities of Obinutuzumab.
Pentoxifylline Pentoxifylline may increase the hypotensive activities of Macitentan.
Rituximab Macitentan may increase the hypotensive activities of Rituximab.
Midodrine Midodrine may decrease the antihypertensive activities of Macitentan.
Isoetharine Isoetharine may decrease the antihypertensive activities of Macitentan.
Zolmitriptan Zolmitriptan may decrease the antihypertensive activities of Macitentan.
Protriptyline Protriptyline may decrease the antihypertensive activities of Macitentan.
Norepinephrine Norepinephrine may decrease the antihypertensive activities of Macitentan.
Phenylephrine Phenylephrine may decrease the antihypertensive activities of Macitentan.
Phenylpropanolamine Phenylpropanolamine may decrease the antihypertensive activities of Macitentan.
Droperidol Droperidol may decrease the antihypertensive activities of Macitentan.
Amoxapine Amoxapine may decrease the antihypertensive activities of Macitentan.
Doxapram Doxapram may decrease the antihypertensive activities of Macitentan.
Atropine Atropine may decrease the antihypertensive activities of Macitentan.
Metaraminol Metaraminol may decrease the antihypertensive activities of Macitentan.
Nicergoline Nicergoline may decrease the antihypertensive activities of Macitentan.
Methoxamine Methoxamine may decrease the antihypertensive activities of Macitentan.
Propiomazine Propiomazine may decrease the antihypertensive activities of Macitentan.
Orciprenaline Orciprenaline may decrease the antihypertensive activities of Macitentan.
Phenmetrazine Phenmetrazine may decrease the antihypertensive activities of Macitentan.
Trifluoperazine Trifluoperazine may decrease the antihypertensive activities of Macitentan.
Pseudoephedrine Pseudoephedrine may decrease the antihypertensive activities of Macitentan.
Ritodrine Ritodrine may decrease the antihypertensive activities of Macitentan.
Flupentixol Flupentixol may decrease the antihypertensive activities of Macitentan.
Bitolterol Bitolterol may decrease the antihypertensive activities of Macitentan.
Diethylpropion Diethylpropion may decrease the antihypertensive activities of Macitentan.
Naratriptan Naratriptan may decrease the antihypertensive activities of Macitentan.
Formoterol Formoterol may decrease the antihypertensive activities of Macitentan.
Frovatriptan Frovatriptan may decrease the antihypertensive activities of Macitentan.
Isoprenaline Isoprenaline may decrease the antihypertensive activities of Macitentan.
Arbutamine Arbutamine may decrease the antihypertensive activities of Macitentan.
Lisdexamfetamine Lisdexamfetamine may decrease the antihypertensive activities of Macitentan.
Fenoterol Fenoterol may decrease the antihypertensive activities of Macitentan.
Pirbuterol Pirbuterol may decrease the antihypertensive activities of Macitentan.
Ephedra sinica root Ephedra sinica root may decrease the antihypertensive activities of Macitentan.
Ephedrine Ephedrine may decrease the antihypertensive activities of Macitentan.
Mephentermine Mephentermine may decrease the antihypertensive activities of Macitentan.
Procaterol Procaterol may decrease the antihypertensive activities of Macitentan.
Methotrimeprazine Methotrimeprazine may decrease the antihypertensive activities of Macitentan.
Clenbuterol Clenbuterol may decrease the antihypertensive activities of Macitentan.
Bambuterol Bambuterol may decrease the antihypertensive activities of Macitentan.
MMDA MMDA may decrease the antihypertensive activities of Macitentan.
Midomafetamine Midomafetamine may decrease the antihypertensive activities of Macitentan.
2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Macitentan.
4-Methoxyamphetamine 4-Methoxyamphetamine may decrease the antihypertensive activities of Macitentan.
4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Macitentan.
Tenamfetamine Tenamfetamine may decrease the antihypertensive activities of Macitentan.
Chlorphentermine Chlorphentermine may decrease the antihypertensive activities of Macitentan.
Dextroamphetamine Dextroamphetamine may decrease the antihypertensive activities of Macitentan.
Phendimetrazine Phendimetrazine may decrease the antihypertensive activities of Macitentan.
Periciazine Periciazine may decrease the antihypertensive activities of Macitentan.
Acepromazine Acepromazine may decrease the antihypertensive activities of Macitentan.
Thioproperazine Thioproperazine may decrease the antihypertensive activities of Macitentan.
Epicaptopril Epicaptopril may decrease the antihypertensive activities of Macitentan.
1-benzylimidazole 1-benzylimidazole may decrease the antihypertensive activities of Macitentan.
Amineptine Amineptine may decrease the antihypertensive activities of Macitentan.
Amibegron Amibegron may decrease the antihypertensive activities of Macitentan.
Naluzotan Naluzotan may decrease the antihypertensive activities of Macitentan.
Pizotifen Pizotifen may decrease the antihypertensive activities of Macitentan.
Solabegron Solabegron may decrease the antihypertensive activities of Macitentan.
Esmirtazapine Esmirtazapine may decrease the antihypertensive activities of Macitentan.
Nitrous oxide Nitrous oxide may decrease the antihypertensive activities of Macitentan.
Xylometazoline Xylometazoline may decrease the antihypertensive activities of Macitentan.
Isometheptene Isometheptene may decrease the antihypertensive activities of Macitentan.
Levonordefrin Levonordefrin may decrease the antihypertensive activities of Macitentan.
Naphazoline Naphazoline may decrease the antihypertensive activities of Macitentan.
Saralasin Saralasin may decrease the antihypertensive activities of Macitentan.
Tetryzoline Tetryzoline may decrease the antihypertensive activities of Macitentan.
Cinitapride Cinitapride may decrease the antihypertensive activities of Macitentan.
Tyramine Tyramine may decrease the antihypertensive activities of Macitentan.
Adrafinil Adrafinil may decrease the antihypertensive activities of Macitentan.
Ifenprodil Ifenprodil may decrease the antihypertensive activities of Macitentan.
Hexoprenaline Hexoprenaline may decrease the antihypertensive activities of Macitentan.
Etilefrine Etilefrine may decrease the antihypertensive activities of Macitentan.
Butriptyline Butriptyline may decrease the antihypertensive activities of Macitentan.
Olodaterol Olodaterol may decrease the antihypertensive activities of Macitentan.
Dosulepin Dosulepin may decrease the antihypertensive activities of Macitentan.
Cirazoline Cirazoline may decrease the antihypertensive activities of Macitentan.
Synephrine Synephrine may decrease the antihypertensive activities of Macitentan.
Oxaprotiline Oxaprotiline may decrease the antihypertensive activities of Macitentan.
Iofetamine I-123 Iofetamine I-123 may decrease the antihypertensive activities of Macitentan.
Racepinephrine Racepinephrine may decrease the antihypertensive activities of Macitentan.
Amitraz Amitraz may decrease the antihypertensive activities of Macitentan.
Medetomidine Medetomidine may decrease the antihypertensive activities of Macitentan.
Xylazine Xylazine may decrease the antihypertensive activities of Macitentan.
Atipamezole Atipamezole may decrease the antihypertensive activities of Macitentan.
Ractopamine Ractopamine may decrease the antihypertensive activities of Macitentan.
Romifidine Romifidine may decrease the antihypertensive activities of Macitentan.
Detomidine Detomidine may decrease the antihypertensive activities of Macitentan.
Tetrahydrocannabivarin Tetrahydrocannabivarin may decrease the antihypertensive activities of Macitentan.
Anisodamine Anisodamine may decrease the antihypertensive activities of Macitentan.
PF-00610355 PF-00610355 may decrease the antihypertensive activities of Macitentan.
Ritobegron Ritobegron may decrease the antihypertensive activities of Macitentan.
Abediterol Abediterol may decrease the antihypertensive activities of Macitentan.
Tulobuterol Tulobuterol may decrease the antihypertensive activities of Macitentan.

Target Protein

Endothelin-1 receptor EDNRA
Endothelin receptor type B EDNRB

Referensi & Sumber

Synthesis reference: Bolli MH, Boss C, Binkert C, Buchmann S, Bur D, Hess P, Iglarz M, Meyer S, Rein J, Rey M, Treiber A, Clozel M, Fischli W, Weller T: The discovery of N-5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxyethoxy]-4-pyrimidinyl]-N'-p ropylsulfamide (Macitentan), an orally active, potent dual endothelin receptor antagonist. J Med Chem. 2012 Sep 13;55(17):7849-61. doi: 10.1021/jm3009103. Epub 2012 Aug 16. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/22862294)
Artikel (PubMed)
  • PMID: 26956245
    Davenport AP, Hyndman KA, Dhaun N, Southan C, Kohan DE, Pollock JS, Pollock DM, Webb DJ, Maguire JJ: Endothelin. Pharmacol Rev. 2016 Apr;68(2):357-418. doi: 10.1124/pr.115.011833.
  • PMID: 29540357
    Thenappan T, Ormiston ML, Ryan JJ, Archer SL: Pulmonary arterial hypertension: pathogenesis and clinical management. BMJ. 2018 Mar 14;360:j5492. doi: 10.1136/bmj.j5492.
  • PMID: 29719121
    Bedan M, Grimm D, Wehland M, Simonsen U, Infanger M, Kruger M: A Focus on Macitentan in the Treatment of Pulmonary Arterial Hypertension. Basic Clin Pharmacol Toxicol. 2018 Aug;123(2):103-113. doi: 10.1111/bcpt.13033. Epub 2018 Jun 5.
  • PMID: 25860376
    Sidharta PN, Treiber A, Dingemanse J: Clinical pharmacokinetics and pharmacodynamics of the endothelin receptor antagonist macitentan. Clin Pharmacokinet. 2015 May;54(5):457-71. doi: 10.1007/s40262-015-0255-5.

Contoh Produk & Brand

Produk: 11 • International brands: 0
Produk
  • Opsumit
    Tablet, for suspension • 2.5 mg • Oral • EU • Approved
  • Opsumit
    Tablet, film coated • 10 mg • Oral • EU • Approved
  • Opsumit
    Tablet, film coated • 10 mg • Oral • EU • Approved
  • Opsumit
    Tablet, film coated • 10 mg • Oral • EU • Approved
  • Opsumit
    Tablet, film coated • 10 mg/1 • Oral • US • Approved
  • Opsumit
    Tablet • 10 mg • Oral • Canada • Approved
  • Opsynvi
    Tablet • - • Oral • Canada • Approved
  • Opsynvi
    Tablet, film coated • - • Oral • US • Approved
Menampilkan 8 dari 11 produk.

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