Detail

MACITENTAN

Description

Name: MACITENTAN
Type: small molecule
Groups: approved
Indication: Macitentan is indicated for patients with pulmonary arterial hypertension.
Accession Number: DB08932 ( DB08932)
Description: Macitentan was approved in October 2013. It is indicated for patients with pulmonary arterial hypertension, and is marketed under the brand name Opsumit. Macitentan is an antagonist/blocker of endothelin receptors on blood vessels and smooth muscle, and, thus, blocks the stimulation of vasculature hypertrophy, inflammation, fibrosis, proliferation, and vasoconstriction. Similar to all drugs acting on the renin-angiotensin system, macitentan is associated with embryo and fetal toxicity, so it should not be used in pregnancy and has special precautions that must be followed for all females of child-bearing age.
Structure:
Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Opsumittablet10 mgoral15-01-2014Canada
Opsumittablet, film coated10 mg/1oral01-10-2013US

Generic Prescription Products: Not Available
Over the Counter Products: Not Available
International Brands
  • No Brands

Brand Names
  • No Brands

Brand Mixtures
Brand NameIngredients
OpsumitMACITENTAN
OpsumitMACITENTAN

Categories
  • Vasodilator Agents

Pharmacology

Indication: Macitentan is indicated for patients with pulmonary arterial hypertension.
Pharmacodynamics: Not Available
Mechanism of action: Macitentan is an antagonist/blocker of endothelin receptors. Endothelin receptors are found in the endothelial cells of blood vessels and smooth muscle. Macitentan binds to the receptors, endothelin A and B (ETA and ETB), which prevents the agonist endothelin -1 (ET-1) from binding and stimulating the ETA and ETB receptors.
Absorption: Macitentan is administered orally, and it take about 8 hours for maximum plasma concentrations to be reached.
Volume of distribution:
    Macitentan has a volume of distribution of 50L.

Protein binding: Macitentan is >99% bound to plasma proteins, which are mainly albumin
Metabolism: Not Available
Route of elimination: Eliminated 50% through urine and 24% through feces.
Half life: The half life of macitentan is 16 hours, and the half life of it's active metabolite is 48 hours.
Clearance: Not Available
Toxicity: Macitentan has a black box warning of embryo-fetal toxicity. Special precautions must be taken for all females of child-bearing age, and women who are pregnant must not be given macitentan.
Affected organisms
  • Not Available

SNP Mediated Adverse Drug Reactions
  • Not Available

Pharmacoeconomics

Manufacturers:
  • Not Available

Packagers:
  • Not Available

Dosage forms
FormRouteStrength
Tabletoral10 mg
Tablet, film coatedoral10 mg/1

Prices
Unit descriptionCostUnit

Patents
CountryPatent NumberApprovedExpires (estimated)

Interactions

Drug Interactions
DrugInteraction
AprepitantThe serum concentration of MACITENTAN can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of MACITENTAN can be increased when it is combined with Atazanavir.
BexaroteneThe serum concentration of MACITENTAN can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of MACITENTAN can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of MACITENTAN can be decreased when it is combined with Bosentan.
CarbamazepineThe serum concentration of MACITENTAN can be decreased when it is combined with Carbamazepine.
CeritinibThe serum concentration of MACITENTAN can be increased when it is combined with Ceritinib.
ClarithromycinThe serum concentration of MACITENTAN can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of MACITENTAN can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of MACITENTAN can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of MACITENTAN can be decreased when it is combined with Dabrafenib.
DarunavirThe serum concentration of MACITENTAN can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of MACITENTAN can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of MACITENTAN can be decreased when it is combined with Deferasirox.
EnzalutamideThe serum concentration of MACITENTAN can be decreased when it is combined with Enzalutamide.
FluconazoleThe metabolism of MACITENTAN can be decreased when combined with Fluconazole.
FosaprepitantThe serum concentration of MACITENTAN can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of MACITENTAN can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of MACITENTAN can be increased when it is combined with Fusidic Acid.
IdelalisibThe serum concentration of MACITENTAN can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of MACITENTAN can be increased when it is combined with Indinavir.
ItraconazoleThe serum concentration of MACITENTAN can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of MACITENTAN can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of MACITENTAN can be increased when it is combined with Ketoconazole.
LuliconazoleThe serum concentration of MACITENTAN can be increased when it is combined with Luliconazole.
MifepristoneThe serum concentration of MACITENTAN can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of MACITENTAN can be decreased when it is combined with Mitotane.
NefazodoneThe serum concentration of MACITENTAN can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of MACITENTAN can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of MACITENTAN can be increased when it is combined with Netupitant.
PalbociclibThe serum concentration of MACITENTAN can be increased when it is combined with Palbociclib.
PhenobarbitalThe serum concentration of MACITENTAN can be decreased when it is combined with Phenobarbital.
PhenytoinThe serum concentration of MACITENTAN can be decreased when it is combined with Phenytoin.
PosaconazoleThe serum concentration of MACITENTAN can be increased when it is combined with Posaconazole.
PrimidoneThe serum concentration of MACITENTAN can be decreased when it is combined with Primidone.
RifabutinThe serum concentration of MACITENTAN can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of MACITENTAN can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of MACITENTAN can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of MACITENTAN can be increased when it is combined with Ritonavir.
SaquinavirThe serum concentration of MACITENTAN can be increased when it is combined with Saquinavir.
SiltuximabThe serum concentration of MACITENTAN can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of MACITENTAN can be increased when it is combined with Simeprevir.
St. John's WortThe serum concentration of MACITENTAN can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of MACITENTAN can be increased when it is combined with Stiripentol.
TelaprevirThe serum concentration of MACITENTAN can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of MACITENTAN can be increased when it is combined with Telithromycin.
TocilizumabThe serum concentration of MACITENTAN can be decreased when it is combined with Tocilizumab.
VoriconazoleThe serum concentration of MACITENTAN can be increased when it is combined with Voriconazole.

Food Interactions:
  • Can be taken with or without food.

Taxonomy

Kingdom: Organic compounds
Super Class: Not Available
Class: Not Available
Sub Class: Not Available
Direct Parent: Not Available
Alternative Parents:
  • Alkyl aryl ethers
  • Aminopyrimidines and derivatives
  • Aryl bromides
  • Azacyclic compounds
  • Bromobenzenes
  • Halopyrimidines
  • Heteroaromatic compounds
  • Hydrocarbon derivatives
  • Imidolactams
  • Organobromides
  • Organonitrogen compounds
  • Sulfuric acid diamides

substituent:
  • 5-phenylpyrimidine
  • Alkyl aryl ether
  • Aminopyrimidine
  • Aromatic heteromonocyclic compound
  • Aryl bromide
  • Aryl halide
  • Azacycle
  • Benzenoid
  • Bromobenzene
  • Ether
  • Halobenzene
  • Halopyrimidine
  • Heteroaromatic compound
  • Hydrocarbon derivative
  • Imidolactam
  • Monocyclic benzene moiety
  • Organic sulfuric acid or derivatives
  • Organobromide
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Sulfuric acid diamide

References

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)oxy]ethoxy]-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
General 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)oxy]ethoxy]-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 # FDA label. # Lexicomp.
External Links:
ResourceLink
RxListhttp://www.rxlist.com/opsumit-drug.htm
Drugs.comhttp://www.drugs.com/cons/macitentan.html

ATC Codes:
  • Array

AHFS Codes:
  • Not Available

MSDS: Download
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