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:
Generic Prescription Products: Not Available
Over the Counter Products: Not Available
Prescription Products:
International Brands
Brand Names
Brand Mixtures
Categories
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:
| Name | Dosage | Strength | Route | Marketing Start | Marketing End | Country |
| Opsumit | tablet | 10 mg | oral | 15-01-2014 | Canada | |
| Opsumit | tablet, film coated | 10 mg/1 | oral | 01-10-2013 | US |
Generic Prescription Products: Not Available
Over the Counter Products: Not Available
Prescription Products:
| Name | Dosage | Strength | Route | Marketing Start | Marketing End | Country |
| Opsumit | tablet | 10 mg | oral | 15-01-2014 | Canada | |
| Opsumit | tablet, film coated | 10 mg/1 | oral | 01-10-2013 | US |
International Brands
- No Brands
Brand Names
- No Brands
Brand Mixtures
| Brand Name | Ingredients |
|---|---|
| Opsumit | MACITENTAN |
| Opsumit | MACITENTAN |
| Brand Name | Ingredients |
|---|---|
| Opsumit | MACITENTAN |
| Opsumit | MACITENTAN |
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:
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
SNP Mediated Adverse Drug Reactions
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:
Packagers:
Dosage forms
Prices
Patents
- Not Available
Packagers:
- Not Available
Dosage forms
| Form | Route | Strength |
|---|---|---|
| Tablet | oral | 10 mg |
| Tablet, film coated | oral | 10 mg/1 |
| Form | Route | Strength |
|---|---|---|
| Tablet | oral | 10 mg |
| Tablet, film coated | oral | 10 mg/1 |
Prices
| Unit description | Cost | Unit |
|---|
| Unit description | Cost | Unit |
|---|
Patents
| Country | Patent Number | Approved | Expires (estimated) |
|---|
Interactions
Drug Interactions
Food Interactions:
| Drug | Interaction |
|---|---|
| Aprepitant | The serum concentration of MACITENTAN can be increased when it is combined with Aprepitant. |
| Atazanavir | The serum concentration of MACITENTAN can be increased when it is combined with Atazanavir. |
| Bexarotene | The serum concentration of MACITENTAN can be decreased when it is combined with Bexarotene. |
| Boceprevir | The serum concentration of MACITENTAN can be increased when it is combined with Boceprevir. |
| Bosentan | The serum concentration of MACITENTAN can be decreased when it is combined with Bosentan. |
| Carbamazepine | The serum concentration of MACITENTAN can be decreased when it is combined with Carbamazepine. |
| Ceritinib | The serum concentration of MACITENTAN can be increased when it is combined with Ceritinib. |
| Clarithromycin | The serum concentration of MACITENTAN can be increased when it is combined with Clarithromycin. |
| Cobicistat | The serum concentration of MACITENTAN can be increased when it is combined with Cobicistat. |
| Conivaptan | The serum concentration of MACITENTAN can be increased when it is combined with Conivaptan. |
| Dabrafenib | The serum concentration of MACITENTAN can be decreased when it is combined with Dabrafenib. |
| Darunavir | The serum concentration of MACITENTAN can be increased when it is combined with Darunavir. |
| Dasatinib | The serum concentration of MACITENTAN can be increased when it is combined with Dasatinib. |
| Deferasirox | The serum concentration of MACITENTAN can be decreased when it is combined with Deferasirox. |
| Enzalutamide | The serum concentration of MACITENTAN can be decreased when it is combined with Enzalutamide. |
| Fluconazole | The metabolism of MACITENTAN can be decreased when combined with Fluconazole. |
| Fosaprepitant | The serum concentration of MACITENTAN can be increased when it is combined with Fosaprepitant. |
| Fosphenytoin | The serum concentration of MACITENTAN can be decreased when it is combined with Fosphenytoin. |
| Fusidic Acid | The serum concentration of MACITENTAN can be increased when it is combined with Fusidic Acid. |
| Idelalisib | The serum concentration of MACITENTAN can be increased when it is combined with Idelalisib. |
| Indinavir | The serum concentration of MACITENTAN can be increased when it is combined with Indinavir. |
| Itraconazole | The serum concentration of MACITENTAN can be increased when it is combined with Itraconazole. |
| Ivacaftor | The serum concentration of MACITENTAN can be increased when it is combined with Ivacaftor. |
| Ketoconazole | The serum concentration of MACITENTAN can be increased when it is combined with Ketoconazole. |
| Luliconazole | The serum concentration of MACITENTAN can be increased when it is combined with Luliconazole. |
| Mifepristone | The serum concentration of MACITENTAN can be increased when it is combined with Mifepristone. |
| Mitotane | The serum concentration of MACITENTAN can be decreased when it is combined with Mitotane. |
| Nefazodone | The serum concentration of MACITENTAN can be increased when it is combined with Nefazodone. |
| Nelfinavir | The serum concentration of MACITENTAN can be increased when it is combined with Nelfinavir. |
| Netupitant | The serum concentration of MACITENTAN can be increased when it is combined with Netupitant. |
| Palbociclib | The serum concentration of MACITENTAN can be increased when it is combined with Palbociclib. |
| Phenobarbital | The serum concentration of MACITENTAN can be decreased when it is combined with Phenobarbital. |
| Phenytoin | The serum concentration of MACITENTAN can be decreased when it is combined with Phenytoin. |
| Posaconazole | The serum concentration of MACITENTAN can be increased when it is combined with Posaconazole. |
| Primidone | The serum concentration of MACITENTAN can be decreased when it is combined with Primidone. |
| Rifabutin | The serum concentration of MACITENTAN can be decreased when it is combined with Rifabutin. |
| Rifampicin | The serum concentration of MACITENTAN can be decreased when it is combined with Rifampicin. |
| Rifapentine | The serum concentration of MACITENTAN can be decreased when it is combined with Rifapentine. |
| Ritonavir | The serum concentration of MACITENTAN can be increased when it is combined with Ritonavir. |
| Saquinavir | The serum concentration of MACITENTAN can be increased when it is combined with Saquinavir. |
| Siltuximab | The serum concentration of MACITENTAN can be decreased when it is combined with Siltuximab. |
| Simeprevir | The serum concentration of MACITENTAN can be increased when it is combined with Simeprevir. |
| St. John's Wort | The serum concentration of MACITENTAN can be decreased when it is combined with St. John's Wort. |
| Stiripentol | The serum concentration of MACITENTAN can be increased when it is combined with Stiripentol. |
| Telaprevir | The serum concentration of MACITENTAN can be increased when it is combined with Telaprevir. |
| Telithromycin | The serum concentration of MACITENTAN can be increased when it is combined with Telithromycin. |
| Tocilizumab | The serum concentration of MACITENTAN can be decreased when it is combined with Tocilizumab. |
| Voriconazole | The serum concentration of MACITENTAN can be increased when it is combined with Voriconazole. |
| Drug | Interaction |
|---|---|
| Aprepitant | The serum concentration of MACITENTAN can be increased when it is combined with Aprepitant. |
| Atazanavir | The serum concentration of MACITENTAN can be increased when it is combined with Atazanavir. |
| Bexarotene | The serum concentration of MACITENTAN can be decreased when it is combined with Bexarotene. |
| Boceprevir | The serum concentration of MACITENTAN can be increased when it is combined with Boceprevir. |
| Bosentan | The serum concentration of MACITENTAN can be decreased when it is combined with Bosentan. |
| Carbamazepine | The serum concentration of MACITENTAN can be decreased when it is combined with Carbamazepine. |
| Ceritinib | The serum concentration of MACITENTAN can be increased when it is combined with Ceritinib. |
| Clarithromycin | The serum concentration of MACITENTAN can be increased when it is combined with Clarithromycin. |
| Cobicistat | The serum concentration of MACITENTAN can be increased when it is combined with Cobicistat. |
| Conivaptan | The serum concentration of MACITENTAN can be increased when it is combined with Conivaptan. |
| Dabrafenib | The serum concentration of MACITENTAN can be decreased when it is combined with Dabrafenib. |
| Darunavir | The serum concentration of MACITENTAN can be increased when it is combined with Darunavir. |
| Dasatinib | The serum concentration of MACITENTAN can be increased when it is combined with Dasatinib. |
| Deferasirox | The serum concentration of MACITENTAN can be decreased when it is combined with Deferasirox. |
| Enzalutamide | The serum concentration of MACITENTAN can be decreased when it is combined with Enzalutamide. |
| Fluconazole | The metabolism of MACITENTAN can be decreased when combined with Fluconazole. |
| Fosaprepitant | The serum concentration of MACITENTAN can be increased when it is combined with Fosaprepitant. |
| Fosphenytoin | The serum concentration of MACITENTAN can be decreased when it is combined with Fosphenytoin. |
| Fusidic Acid | The serum concentration of MACITENTAN can be increased when it is combined with Fusidic Acid. |
| Idelalisib | The serum concentration of MACITENTAN can be increased when it is combined with Idelalisib. |
| Indinavir | The serum concentration of MACITENTAN can be increased when it is combined with Indinavir. |
| Itraconazole | The serum concentration of MACITENTAN can be increased when it is combined with Itraconazole. |
| Ivacaftor | The serum concentration of MACITENTAN can be increased when it is combined with Ivacaftor. |
| Ketoconazole | The serum concentration of MACITENTAN can be increased when it is combined with Ketoconazole. |
| Luliconazole | The serum concentration of MACITENTAN can be increased when it is combined with Luliconazole. |
| Mifepristone | The serum concentration of MACITENTAN can be increased when it is combined with Mifepristone. |
| Mitotane | The serum concentration of MACITENTAN can be decreased when it is combined with Mitotane. |
| Nefazodone | The serum concentration of MACITENTAN can be increased when it is combined with Nefazodone. |
| Nelfinavir | The serum concentration of MACITENTAN can be increased when it is combined with Nelfinavir. |
| Netupitant | The serum concentration of MACITENTAN can be increased when it is combined with Netupitant. |
| Palbociclib | The serum concentration of MACITENTAN can be increased when it is combined with Palbociclib. |
| Phenobarbital | The serum concentration of MACITENTAN can be decreased when it is combined with Phenobarbital. |
| Phenytoin | The serum concentration of MACITENTAN can be decreased when it is combined with Phenytoin. |
| Posaconazole | The serum concentration of MACITENTAN can be increased when it is combined with Posaconazole. |
| Primidone | The serum concentration of MACITENTAN can be decreased when it is combined with Primidone. |
| Rifabutin | The serum concentration of MACITENTAN can be decreased when it is combined with Rifabutin. |
| Rifampicin | The serum concentration of MACITENTAN can be decreased when it is combined with Rifampicin. |
| Rifapentine | The serum concentration of MACITENTAN can be decreased when it is combined with Rifapentine. |
| Ritonavir | The serum concentration of MACITENTAN can be increased when it is combined with Ritonavir. |
| Saquinavir | The serum concentration of MACITENTAN can be increased when it is combined with Saquinavir. |
| Siltuximab | The serum concentration of MACITENTAN can be decreased when it is combined with Siltuximab. |
| Simeprevir | The serum concentration of MACITENTAN can be increased when it is combined with Simeprevir. |
| St. John's Wort | The serum concentration of MACITENTAN can be decreased when it is combined with St. John's Wort. |
| Stiripentol | The serum concentration of MACITENTAN can be increased when it is combined with Stiripentol. |
| Telaprevir | The serum concentration of MACITENTAN can be increased when it is combined with Telaprevir. |
| Telithromycin | The serum concentration of MACITENTAN can be increased when it is combined with Telithromycin. |
| Tocilizumab | The serum concentration of MACITENTAN can be decreased when it is combined with Tocilizumab. |
| Voriconazole | The 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:
substituent:
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:
ATC Codes:
AHFS Codes:
MSDS: Download
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:
| Resource | Link |
|---|---|
| RxList | http://www.rxlist.com/opsumit-drug.htm |
| Drugs.com | http://www.drugs.com/cons/macitentan.html |
| Resource | Link |
|---|---|
| RxList | http://www.rxlist.com/opsumit-drug.htm |
| Drugs.com | http://www.drugs.com/cons/macitentan.html |
ATC Codes:
- Array
AHFS Codes:
- Not Available
MSDS: Download