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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/11 23:47:08」(JST)
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Bosentan
|
| Systematic (IUPAC) name |
|
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide
|
| Clinical data |
| Trade names |
Tracleer |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a605001 |
Pregnancy
category |
|
| Legal status |
|
Routes of
administration |
Oral |
| Pharmacokinetic data |
| Bioavailability |
50% |
| Protein binding |
>98% |
| Metabolism |
Hepatic |
| Biological half-life |
5 hours |
| Identifiers |
| CAS Number |
147536-97-8 Y |
| ATC code |
C02KX01 |
| PubChem |
CID: 104865 |
| IUPHAR/BPS |
3494 |
| DrugBank |
DB00559 Y |
| ChemSpider |
94651 Y |
| UNII |
XUL93R30K2 Y |
| KEGG |
D01227 N |
| ChEBI |
CHEBI:51450 Y |
| ChEMBL |
CHEMBL957 Y |
| Chemical data |
| Formula |
C27H29N5O6S |
| Molecular mass |
551.614 g/mol |
SMILES
-
CC(C)(C)c1ccc(cc1)S(=O)(=O)Nc2c(c(nc(n2)c3ncccn3)OCCO)Oc4ccccc4OC
|
InChI
-
InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32) Y
-
Key:GJPICJJJRGTNOD-UHFFFAOYSA-N Y
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| NY (what is this?) (verify) |
Bosentan is a dual endothelin receptor antagonist used in the treatment of pulmonary artery hypertension (PAH). It is licensed in the United States, the European Union and other countries by Actelion Pharmaceuticals for the management of PAH under the trade name Tracleer.
Contents
- 1 Mechanism of action
- 2 Clinical uses
- 3 Warnings
- 4 See also
- 5 References
- 6 External links
Mechanism of action
Bosentan is a competitive antagonist of endothelin-1 at the endothelin-A (ET-A) and endothelin-B (ET-B) receptors. Under normal conditions, endothelin-1 binding of ET-A or ET-B receptors causes constriction of the pulmonary blood vessels. By blocking this interaction, bosentan decreases pulmonary vascular resistance. Bosentan has a slightly higher affinity for ET-A than ET-B.[1]
Clinical uses
Bosentan is indicated mainly for the treatment of pulmonary hypertension. In 2007, Bosentan was also approved in the European Union for reducing the number of new digital ulcers in patients with systemic sclerosis and ongoing digital ulcer disease.[citation needed]
In the United States, Bosentan is indicated for the treatment of pulmonary arterial hypertension (WHO Group I) in patients with WHO Class II-IV symptoms, to improve exercise capacity and decrease the rate of clinical worsening.[2]
Warnings
Due to potential hepatotoxicity, the FDA requires monthly monitoring of liver function tests while taking Bosentan.
Bosentan use requires hematocrit monitoring due to potential onset of anemia.[3]
Hormone-based contraception is not possible in women taking Bosentan, due to a pharmacokinetic interaction.[4] Therefore, other highly reliable forms of contraception should be used instead.
Bosentan is contraindicated in pregnancy because of its teratogenicity (Pregnancy Category X). [5] [6]
See also
- Ambrisentan
- Darusentan
- Sitaxentan
References
- ^ Funke C, Farr M, Werner B, Dittmann S, Uberla K, Piper C, Niehaus K, Horstkotte D (Apr 2010). "Antiviral effect of Bosentan and Valsartan during coxsackievirus B3 infection of human endothelial cells.". Journal of General Virology 91 (8): 1959–1570. doi:10.1099/vir.0.020065-0. PMID 20392896.
- ^ http://www.tracleer.com/pdf/09%20276%2001%2000%200809_Tra%20PI_4%20Pg_081409pdf.pdf
- ^ http://www.ionchannels.org/showabstract.php?pmid=15875338
- ^ http://www.ionchannels.org/showabstract.php?pmid=15875338
- ^ http://www.medicinescomplete.com/mc/bnf/current/PHP1044-bosentan.htm?q=bosentan&t=search&ss=text&p=1#_hit
- ^ http://www.nzf.org.nz/nzf_1183.html
External links
- PubPK - Bosentan pharmacokinetics
- Tracleer official website
- - Tracleer Prescribing Information
|
Medications used in the management of pulmonary arterial hypertension (B01, C02)
|
|
| Prostacyclin analogues |
- Beraprost
- Epoprostenol
- Iloprost
- Selexipag
- Treprostinil
|
|
| Endothelin receptor antagonists |
- Ambrisentan
- Bosentan
- Macitentan
- Sitaxentan
|
|
| PDE5 inhibitors |
|
|
| sGC stimulators |
|
|
| Adjunctive therapy |
- Calcium channel blockers
- Diuretics
- Digoxin
- Oxygen therapy
- Warfarin
|
|
|
Index of the respiratory system
|
|
| Description |
- Anatomy
- Physiology
- Development
|
|
| Disease |
- Congenital
- Neoplasms and cancer
- Chest trauma
- Infection
- common cold
- pneumonia
- tuberculosis
- Other
- Symptoms and signs
|
|
| Treatment |
- Procedures
- Drugs
- nasal
- throat
- obstructive airway diseases
- cough and cold
- histaminergics
- pulmonary arterial hypertension
- other
- Surgery
|
|
|
|
Sympatholytic (and closely related) antihypertensives (C02)
|
|
Sympatholytics
(antagonize α-adrenergic
vasoconstriction) |
| Central |
| α2 agonist |
- Clonidine
- Guanabenz
- Guanfacine
- Methyldopa#
- Tiamenidine‡
|
|
| Adrenergic release inhibitors |
- Bethanidine
- Bretylium
- Debrisoquine
- Guanadrel
- Guanazodine
- Guanethidine
- Guanoclor
- Guanazodine
- Guanoxabenz
- Guanoxan
|
|
| Imidazoline receptor agonist |
|
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| Ganglion-blocking/nicotinic antagonist |
- Hexamethonium‡
- Mecamylamine
- Pentolinium
- Trimethaphan
|
|
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| Peripheral |
| Indirect |
| MAOI |
|
|
| Adrenergic uptake inhibitor |
- Bietaserpine
- Deserpidine
- Methoserpidine
- Rescinnamine
- Reserpine
|
|
| Tyrosine hydroxylase inhibitor |
|
|
|
| Direct |
| α1 blockers |
- Prazosin
- Indoramin
- Trimazosin
- Doxazosin
- Urapidil
|
|
| Non-selective α blocker |
|
|
|
|
|
| Other antagonists |
| Serotonin antagonist |
|
|
| Endothelin antagonist (for PH) |
- dual (Bosentan, Macitentan)
- selective (Ambrisentan, Sitaxentan)
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
Index of the circulatory system
|
|
| Description |
- Anatomy
- Arteries
- head and neck
- arms
- chest
- abdomen
- legs
- Veins
- head and neck
- arms
- chest
- abdomen and pelvis
- legs
- Development
- Cells
- Physiology
|
|
| Disease |
- Congenital
- Neoplasms and cancer
- Lymphatic vessels
- Injury
- Vasculitis
- Other
- Symptoms and signs
|
|
| Treatment |
- Procedures
- Drugs
- beta blockers
- channel blockers
- diuretics
- nonsympatholytic vasodilatory antihypertensives
- peripheral vasodilators
- renin–angiotensin system
- sympatholytic antihypertensives
- vasoprotectives
|
|
|
UpToDate Contents
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English Journal
- Drug-induced cholestasis risk assessment in sandwich-cultured human hepatocytes.
- Oorts M1, Baze A2, Bachellier P3, Heyd B4, Zacharias T5, Annaert P6, Richert L7.
- Toxicology in vitro : an international journal published in association with BIBRA.Toxicol In Vitro.2016 Aug;34:179-86. doi: 10.1016/j.tiv.2016.03.008. Epub 2016 Apr 2.
- Drug-induced cholestasis (DIC) is recognized as one of the prime mechanisms for DILI. Hence, earlier detection of drug candidates with cholestatic signature is crucial. Recently, we introduced an in vitro model for DIC and evaluated its performance with several cholestatic drugs. We presently expand
- PMID 27046439
- Glycosylation of α2δ1 subunit: a sweet talk with Cav1.2 channels.
- Lazniewska J1, Weiss N.
- General physiology and biophysics.Gen Physiol Biophys.2016 Jul;35(3):239-42. doi: 10.4149/gpb_2016017.
- Bosentan, an endothelin-1 (ET) receptor antagonist is an important drug for the effective management of patients with pulmonary arterial hypertension. Bosentan has a rather complicated pharmacokinetics in humans involving multiple physiological components that have a profound influence on its drug d
- PMID 27313275
- Clinical drug-drug interactions of bosentan, a potent endothelial receptor antagonist, with various drugs: Physiological role of enzymes and transporters.
- Srinivas NR1.
- General physiology and biophysics.Gen Physiol Biophys.2016 Jul;35(3):243-58. doi: 10.4149/gpb_2015050. Epub 2016 Apr 5.
- Bosentan, an endothelin-1 (ET) receptor antagonist is an important drug for the effective management of patients with pulmonary arterial hypertension. Bosentan has a rather complicated pharmacokinetics in humans involving multiple physiological components that have a profound influence on its drug d
- PMID 27045668
Japanese Journal
- Chronic Thromboembolic Pulmonary Hypertension Complicated with Homocystinuria
- Ogawa Shinpei,Katayama Tetsuji,Kaikita Koichi,Tsukamoto Masayo,Yamamoto Eiichiro,Yamamuro Megumi,Tanaka Tomoko,Tsujita Kenichi,Kojima Sunao,Tayama Shinji,Hokimoto Seiji,Yamabe Hiroshige,Indo Yasuhiro,Endo Fumio,Matsubara Hiromi,Ogawa Hisao
- Internal Medicine 53(22), 2605-2608, 2014
- … Two years later, the patient was admitted to our hospital due to a worsening of PH. Treatment with bosentan, sildenafil and beraprost, in addition to anti-coagulant therapy, did not improve his PH. Balloon pulmonary angioplasty (BPA) was performed to remove the pulmonary thrombi. …
- NAID 130004713239
- Withdrawal of Epoprostenol Therapy in a Patient with Pulmonary Hypertension Associated with Sjögren's Syndrome
- Fujita Tetsuo,Tanabe Nobuhiro,Kasahara Yasunori,Sugiura Toshihiko,Sakao Seiichiro,Tatsumi Koichiro
- Internal Medicine 53(19), 2237-2240, 2014
- … This case involves a 38-year-old woman with PAH associated with SjS (PAH-SjS) who was transitioned from treatment with long-term intravenous epoprostenol therapy to combination oral therapy containing bosentan and tadalafil. …
- NAID 130004694540
- Successful Bortezomib/dexamethasone Induction Therapy with Lenalidomide in an Elderly Patient with Primary Plasma Cell Leukemia Complicated by Renal Failure and Pulmonary Hypertension
- Tamura Shinobu,Koyama Asumi,Shiotani Chieko,Kurihara Toshio,Nishikawa Akinori,Okamoto Yukiharu,Fujimoto Tokuzo
- Internal Medicine 53(11), 1171-1175, 2014
- … With the patient in remission, the administration of beraprost and bosentan resulted in improvements in the pulmonary hypertension. …
- NAID 130004466329
Related Links
- We are here to help you throughout your journey with pulmonary arterial hypertension (PAH)*. You'll find information about Tracleer (bosentan) and ways to help manage your PAH*. Choose from the information options above and we ...
- Pulmonary Arterial Hypertension related to Congenital Heart Defect A small study with patients with Eisenmenger physiology demonstrated effects of bosentan on exercise and safety that were similar to those seen in other trials in ...
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