Macitentan: Difference between revisions

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{{Drugbox
{{DrugProjectFormSinglePage
| IUPAC_name        = ''N''-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-''N'''-propylsulfamide
|authorTag=
| image            = Macitentan skeletal.svg
| alt              =
| caption          =  


<!-- Clinical data -->
Gerald Chi
| tradename        = Opsumit
| Drugs.com        =
| MedlinePlus      =
| pregnancy_AU      = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US      = X
| pregnancy_category=
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM -->
| legal_US = Rx-only
| legal_status      = FDA approved drug
| routes_of_administration = Oral


<!-- Pharmacokinetic data -->
<!--Overview-->
| bioavailability  =
| protein_bound    =
| metabolism        = Hydrolysis, oxidation ([[CYP3A4]])
| elimination_half-life =
| excretion        = 2/3 urine, 1/3 faeces


<!-- Identifiers -->
|genericName=
| CAS_number        = 441798-33-0
Macitentan
| ATCvet            =
| ATC_prefix        = C02
| ATC_suffix        = KX04
| ATC_supplemental  =
| PubChem          = 16004692
| DrugBank          =
| ChemSpiderID      = 13134960
| ChEBI            = 76607
| synonyms          = ACT-064992


<!-- Chemical data -->
|aOrAn=
| C=19 | H=20 | Br=2 | N=6 | O=4 | S=1
 
| molecular_weight  = 588.273 g/mol
an
| smiles = Brc1ccc(cc1)c3c(ncnc3OCCOc2ncc(Br)cn2)NS(=O)(=O)NCCC
 
| StdInChI = 1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)
|drugClass=
| StdInChIKey = JGCMEBMXRHSZKX-UHFFFAOYSA-N
 
}}
[[endothelin receptor antagonist]]
'''Macitentan''' (trade name '''Opsumit''') is an [[endothelin receptor antagonist]] (ERA) approved for the treatment of [[pulmonary arterial hypertension]] (PAH).<ref name="(3)">Hong, I.S., Coe, H.V., & Catanzaro, L.M. (2014). Macitentan for the treatment of pulmonary arterial hypertension. ''The Annals of Pharmacotherapy, 48'', 1-10.</ref> The other two ERAs marketed as of 2014 are [[bosentan]] and [[ambrisentan]].<ref name="(3)" /> Macitentan is a dual ERA, meaning that it acts as an antagonist of two [[endothelin]] (ET) receptor subtypes, [[Endothelin receptor type A|ET<sub>A</sub>]] and [[Endothelin receptor type B|ET<sub>B</sub>]].<ref name="(3)" /> However, macitentan has a 50-fold increased selectivity for the ETA subtype compared to the ETB subtype.<ref name="(4)">Iglarz, M., Qiu, C., Fischli, W., Morrison, K., Binkert, C., Clozel, M., Hess, P., Capeleto, B., Buchmann, S., Boss, C., Bolli, M.H., Weller, T., Treiber, A., & Gatfield, J. (2008). Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist. ''Journal of Pharmacology and Experimental Therapeutics, 327''(3), 736-745.</ref> The drug received approval from the U.S. [[Food and Drug Administration]] (FDA) on October 13, 2013.<ref>[http://www.actelion.com/en/our-company/news-and-events/index.page?newsId=1736781 Actelion receives us fda approval of Opsumit (macitentan) for the treatment of pulmonary arterial hypertension]. Actelion. Retrieved 22 October 2013.</ref>
 
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=====Condition1=====
 
* Developed by:
 
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* Strength of Evidence:
 
* Dosing Information
 
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=====Condition1=====
 
* Dosing Information
 
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<!--Pediatric Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
 
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:* Dosage
 
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<!--Off-Label Use and Dosage (Pediatric)-->
 
<!--Guideline-Supported Use (Pediatric)-->
 
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<!--Non–Guideline-Supported Use (Pediatric)-->
 
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=====Condition1=====
 
* Dosing Information
 
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<!--Contraindications-->
 
|contraindications=
 
* Condition1
 
<!--Warnings-->
 
|warnings=
 
* Description
 
====Precautions====
 
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<!--Clinical Trials Experience-->
 
|clinicalTrials=
 
There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
 
=====Body as a Whole=====
 
 
 
 
=====Cardiovascular=====
 
 
 
 
=====Digestive=====
 
 
 
 
=====Endocrine=====
 
 
 
 
=====Hematologic and Lymphatic=====
 
 
 
 
=====Metabolic and Nutritional=====
 
 
 
 
=====Musculoskeletal=====
 
 
 
 
=====Neurologic=====
 
 
 
 
=====Respiratory=====
 
 
 
 
=====Skin and Hypersensitivy Reactions=====
 
 
 
 
=====Special Senses=====
 
 
 
 
=====Urogenital=====
 
 
 
 
=====Miscellaneous=====
 
 
 
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|postmarketing=
 
There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
 
=====Body as a Whole=====
 
 
 
=====Cardiovascular=====
 
 
 
=====Digestive=====
 
 
 
=====Endocrine=====
 
 
 
=====Hematologic and Lymphatic=====
 
 
 
=====Metabolic and Nutritional=====
 
 
 
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=====Neurologic=====
 
 
 
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|useInRace=
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|useInRenalImpair=
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|useInHepaticImpair=
There is no FDA guidance on the use of {{PAGENAME}} in patients with hepatic impairment.
 
|useInReproPotential=
There is no FDA guidance on the use of {{PAGENAME}} in women of reproductive potentials and males.
 
|useInImmunocomp=
There is no FDA guidance one the use of {{PAGENAME}} in patients who are immunocompromised.
 
<!--Administration and Monitoring-->
 
|administration=
 
* Oral
 
* Intravenous
 
|monitoring=
 
There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.
 
* Description
 
<!--IV Compatibility-->
 
|IVCompat=
 
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|overdose=
 
===Acute Overdose===
 
====Signs and Symptoms====
 
* Description
 
====Management====
 
* Description
 
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<!--Pharmacology-->
 
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|drugBox=
 
 
 
<!--Mechanism of Action-->
 
|mechAction=
 
*
 
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|structure=
 
*
 
: [[File:{{PAGENAME}}01.png|thumb|none|600px|This image is provided by the National Library of Medicine.]]
 
<!--Pharmacodynamics-->
 
|PD=
 
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<!--Pharmacokinetics-->
 
|PK=
 
There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.
 
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|alcohol=
 
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|brandNames=
 
* ®<ref>{{Cite web | title =  | url = }}</ref>
 
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|lookAlike=


==Mechanism of action==
* A® — B®<ref name="www.ismp.org">{{Cite web  | last =  | first =  | title = http://www.ismp.org | url = http://www.ismp.org | publisher = | date = }}</ref>
===Endothelin and endothelin receptors===
Endothelin (ET) is an extremely potent blood vessel constricting substance that is secreted by endothelial cells.<ref name="(2)">Gatfield, J., Grandjean, C. M., Sasse, T., Clozel, M., & Nayler, O. (2012). Slow receptor dissociation kinetics differentiate macitentan from other endothelin receptor antagonists in pulmonary arterial smooth muscle cells. ''PLoS ONE, 7''(10), e47662. </ref> In the lungs, the most common ET form released is ET-1.<ref name="(2)" /> ET-1 release can occur through both constitutive and non-constitutive pathways.<ref name="(2)" /> Upon release, ET-1 can bind to the ET receptors that are expressed on arterial smooth muscle cells and fibroblasts in the lungs.<ref name="(2)" /> ET receptors are G protein coupled receptors and, when activated, lead to an increase in intracellular calcium levels via the [[Gαq]] signaling pathway.<ref name="(2)" /> The rise in intracellular calcium leads to contraction of the arterial smooth muscle, as well as vascular remodelling due to cell proliferation.<ref name="(2)" /> Prolonged constriction and fibrosis are factors in the pathogenesis of PAH.<ref name="(3)" />


===Role of macitentan===
<!--Drug Shortage Status-->
Macitentan blocks the ET1-dependent rise in intracellular calcium by inhibiting the binding of ET-1 to ET receptors. Blocking of the ETA receptor subtype seems to be of more importance in the treatment of PAH than blocking of ETB, likely because there are higher numbers of ETA receptors than ETB receptors in pulmonary arterial smooth muscle cells.<ref name="(2)" />  


===Experimental pharmacokinetics===
|drugShortage=
Macitentan has slow association kinetics.<ref name="(2)" /> Its potency increases 6.3-fold when it is pre-incubated with pulmonary arterial smooth muscle cells for 120 minutes compared to 10 minutes with pulmonary arterial smooth muscle cells.<ref name="(2)" /> Macitentan also has a high receptor occupancy half-life (approximately 17 minutes) compared to bosentan (approximately 70 seconds) and ambrisentan (approximately 40 seconds).<ref name="(2)" /> This increased receptor occupancy half-life allows macitentan to act as a non-competitive antagonist of ET receptors.<ref name="(2)" /> Bosentan and ambrisentan are both competitive antagonists.<ref name="(2)" />
}}


==Pharmacokinetics==
<!--Pill Image-->
Macitentan is taken as a 10 mg oral dose once a day.<ref name="(3)" /> Its half-life in humans is about 16 hours and steady state is reached by the third day of administration.<ref name="(1)">Bruderer, S., Hopfgartner, G., Seiberling, M., Wank, J., Sidharta, P.N., Treiber, A., & Dingemanse, J. (2012). Absorption, distribution, metabolism, and excretion of macitentan, a dual endothelin receptor antagonist, in humans. ''Xenobiotica, 42''(9), 901-910.</ref> It is absorbed slowly into the plasma.<ref name="(5)">Sidharta, P.N., van Giersbergen, P.L., Halabi, A., & Dingemanse, J. (2011). Macitentan: entry-into-humans study with a new endothelin receptor antagonist. ''Eur J Clin Pharmacol, 67'', 977–984.</ref> Macitentan has an active metabolite, ACT-132577, which reaches its peak plasma concentration about 30 hours after the first dose is administered, and has a half-life of approximately 48 hours.<ref name="(5)" /> Although ACT-132577 has a lower affinity for the ET receptors than its parent compound,<ref name="(4)" /> it does have higher plasma concentrations than macitentan.<ref name="(5)" /> Both compounds can be excreted from the body through the urine or feces.<ref name="(1)" />  


Co-administration of [[ciclosporin]] has only a slight effect on the concentrations of macitentan and its active metabolite, while [[rifampicin]] decreases the [[area under the curve]] (AUC) of the drug's blood plasma concentration by 79%, and [[ketoconazole]] approximately doubles it. This corresponds to the finding that macitentan is mainly metabolised via the liver enzyme [[CYP3A4]].<ref>{{cite pmid|22189899}}</ref>
{{PillImage
|fileName=No image.jpg|This image is provided by the National Library of Medicine.
|drugName=
|NDC=
|drugAuthor=
|ingredients=
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|dosageUnit=
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[[File:ACT-132577 skeletal.svg|thumb|left|ACT-132577, the active metabolite of macitentan]]
<!--Label Display Image-->
{{clear-left}}


==References==
{{LabelImage
{{reflist}}
|fileName={{PAGENAME}}11.png|This image is provided by the National Library of Medicine.
}}


==External links==
{{LabelImage
* [http://www.actelion.nl Actelion home page]
|fileName={{PAGENAME}}11.png|This image is provided by the National Library of Medicine.
}}


{{PAH rx}}
<!--Category-->


[[Category:Endothelin receptor antagonists]]




{{cardiovascular-drug-stub}}
[[Category:Endothelin receptor antagonists]]
[[Category:Antihypertensive agents]]
[[Category:Cardiovascular Drugs]]
[[Category:Drug]]

Revision as of 15:46, 27 July 2014

Macitentan
Black Box Warning
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Gerald Chi

Disclaimer

WikiDoc MAKES NO GUARANTEE OF VALIDITY. WikiDoc is not a professional health care provider, nor is it a suitable replacement for a licensed healthcare provider. WikiDoc is intended to be an educational tool, not a tool for any form of healthcare delivery. The educational content on WikiDoc drug pages is based upon the FDA package insert, National Library of Medicine content and practice guidelines / consensus statements. WikiDoc does not promote the administration of any medication or device that is not consistent with its labeling. Please read our full disclaimer here.

Black Box Warning

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content

Overview

Macitentan is an endothelin receptor antagonist that is FDA approved for the {{{indicationType}}} of . There is a Black Box Warning for this drug as shown here. Common adverse reactions include .

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Condition1
  • Dosing Information
  • Dosage
Condition2
  • Dosing Information
  • Dosage
Condition3
  • Dosing Information
  • Dosage
Condition4
  • Dosing Information
  • Dosage

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Macitentan in adult patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Macitentan in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding FDA-Labeled Use of Macitentan in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Macitentan in pediatric patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Macitentan in pediatric patients.

Contraindications

  • Condition1

Warnings

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content
  • Description

Precautions

  • Description

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Macitentan in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Macitentan in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Drug Interactions

  • Drug
  • Description

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Macitentan in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Macitentan during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Macitentan with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Macitentan with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Macitentan with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Macitentan with respect to specific gender populations.

Race

There is no FDA guidance on the use of Macitentan with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Macitentan in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Macitentan in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Macitentan in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Macitentan in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Macitentan in the drug label.

  • Description

IV Compatibility

There is limited information regarding IV Compatibility of Macitentan in the drug label.

Overdosage

Acute Overdose

Signs and Symptoms

  • Description

Management

  • Description

Chronic Overdose

There is limited information regarding Chronic Overdose of Macitentan in the drug label.

Pharmacology

There is limited information regarding Macitentan Pharmacology in the drug label.

Mechanism of Action

Structure

This image is provided by the National Library of Medicine.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Macitentan in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Macitentan in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Macitentan in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Macitentan in the drug label.

How Supplied

Storage

There is limited information regarding Macitentan Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Macitentan |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Macitentan |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Macitentan in the drug label.

Precautions with Alcohol

  • Alcohol-Macitentan interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

Look-Alike Drug Names

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Empty citation (help)
  2. ↑ "http://www.ismp.org". External link in |title= (help)


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