WordNet
- a complex consisting of an organic base in association with hydrogen chloride
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/16 09:24:22」(JST)
wiki en
Not to be confused with Profadol, Propanol, or Propofol.
| Systematic (IUPAC) name | |
|---|---|
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(RS)-1-(1-methylethylamino)-3-(1-naphthyloxy)propan-2-ol
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| Clinical data | |
| Trade names | Inderal |
| Drugs.com | Monograph |
| License data |
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| Pregnancy category |
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| Routes of administration |
By mouth, rectal, IV |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | 26% |
| Metabolism | Liver (extensive) 1A2, 2D6; minor: 2C19, 3A4 |
| Biological half-life | 4–5 hours |
| Excretion | Kidney (<1%) |
| Identifiers | |
| CAS Number | 525-66-6 Y |
| ATC code | C07AA05 (WHO) |
| PubChem | CID 4946 |
| IUPHAR/BPS | 564 |
| DrugBank | DB00571 Y |
| ChemSpider | 4777 Y |
| UNII | 9Y8NXQ24VQ Y |
| KEGG | D08443 Y |
| ChEBI | CHEBI:8499 Y |
| ChEMBL | CHEMBL27 Y |
| Chemical data | |
| Formula | C16H21NO2 |
| Molar mass | 259.34 g/mol |
| Chirality | Racemic mixture |
|
SMILES
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InChI
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| (verify) | |
Propranolol is a medication of the beta blocker type.[1] It is used to treat high blood pressure, a number of types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, performance anxiety, and essential tremors.[1][2][3] It is used to prevent migraine headaches, and to prevent further heart problems in those with angina or previous heart attacks.[1] It can be taken by mouth or by injection into a vein. The formulation that is taken by mouth comes in short acting and long acting versions. Propranolol appears in the blood after 30 minutes and has a maximum (peak) effect between 60 and 90 minutes when taken by mouth.[1][4]
Common side effects include nausea, abdominal pain, and constipation. It should not be used in those with an already slow heart rate and most of those with heart failure. Quickly stopping the medication in those with coronary artery disease may worsen symptoms. It may worsen the symptoms of asthma. Greater care is recommended in those with liver or kidney problems.[1] Propranolol may possibly cause harmful effects in the baby if taken during pregnancy.[5] Its use during breastfeeding is likely okay but the baby should be monitored for side effects.[6] It is a non-selective beta blocker which works by blocking β-adrenergic receptors.[1]
Propranolol was discovered in 1964.[7][8] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[9] Propranolol is available as a generic medication.[1] The wholesale cost is between 0.24 and 2.16 USD per month.[10] In the United States it costs about 15 USD per month at a typical dose.[1]
Contents
- 1 Medical uses
- 1.1 Cardiovascular
- 1.2 Psychiatric
- 1.2.1 PTSD and phobias
- 1.3 Others
- 2 Adverse effects
- 2.1 Precautions and contraindications
- 2.2 Pregnancy and lactation
- 3 Interactions
- 4 Pharmacokinetics
- 5 Mechanism of action
- 6 History
- 7 Society and culture
- 7.1 Brand names
- 8 Research
- 9 References
- 10 External links
Medical uses
An 80 mg capsule of extended-release propranolol
A mixture of 20 mg and 10 mg propranolol tablets
Propranolol is used for treating various conditions, including:
Cardiovascular
- Hypertension
- Angina pectoris (with the exception of variant angina)
- Tachyarrhythmia
- Myocardial infarction
- Tachycardia (and other sympathetic nervous system symptoms, such as muscle tremor) associated with various conditions, including anxiety, panic, hyperthyroidism, and lithium therapy
- Portal hypertension, to lower portal vein pressure
- Prevention of esophageal variceal bleeding and ascites
While once a first-line treatment for hypertension, the role for beta blockers was downgraded in June 2006 in the United Kingdom to fourth-line, as they do not perform as well as other drugs, particularly in the elderly, and evidence is increasing that the most frequently used beta blockers at usual doses carry an unacceptable risk of provoking type 2 diabetes.[11]
Propranolol is not recommended for the treatment of hypertension by the Eighth Joint National Committee (JNC 8) because a higher rate of the primary composite outcome of cardiovascular death, myocardial infarction, or stroke compared to an angiotensin receptor blocker was noted in one study.[12]
Psychiatric
It is occasionally used to treat performance anxiety.[2] Evidence to support the use in other anxiety disorders is poor.[13] Some experimentation has been conducted in other psychiatric areas:[14]
- Post-traumatic stress disorder (PTSD) and specific phobias (see subsection below)
- Improvement of social communication skills in people with autism spectrum disorder[15]
- Aggressive behavior of patients with brain injuries[16]
- Treating the excessive drinking of fluids in psychogenic polydipsia[17][18]
PTSD and phobias
Propranolol is being investigated as a potential treatment for PTSD.[19][20] Propranolol works to inhibit the actions of norepinephrine, a neurotransmitter that enhances memory consolidation. Individuals given propranolol immediately after trauma experienced fewer stress-related symptoms and lower rates of PTSD than respective control groups who did not receive the drug.[21] Due to the fact that memories and their emotional content are reconsolidated in the hours after they are recalled/re-experienced, propranolol can also diminish the emotional impact of already formed memories; for this reason, it is also being studied in the treatment of specific phobias, such as arachnophobia, dental fear, and social phobia.[22]
Ethical and legal questions have been raised surrounding the use of propranolol-based medications for use as a "memory damper", including: altering memory-recalled evidence during an investigation, modifying behavioral response to past (albeit traumatic) experiences, the regulation of these drugs, and others.[23] However, Hall and Carter have argued that many such objections are "based on wildly exaggerated and unrealistic scenarios that ignore the limited action of propranolol in affecting memory, underplay the debilitating impact that PTSD has on those who suffer from it, and fail to acknowledge the extent to which drugs like alcohol are already used for this purpose."[24]
Others
- Essential tremor. Evidence for use for akathisia however is insufficient[25]
- Migraine and cluster headache prevention[26][27] and in primary exertional headache[28]
- Hyperhidrosis (excessive sweating)
- Proliferating infantile hemangioma
- Glaucoma
- Thyrotoxicosis by deiodinase inhibition
Propranolol may be used to treat severe infantile hemangiomas (IHs). This treatment shows promise as being superior to corticosteroids when treating IHs. Extensive clinical case evidence and a small controlled trial support its efficacy.[29]
Adverse effects
See also: Beta blocker § Adverse_effects
Due to the high penetration across the blood-brain barrier, lipophilic beta blockers such as propranolol and metoprolol are more likely than other less lipophilic beta blockers to cause sleep disturbances such as insomnia and vivid dreams, and nightmares.[30] Dreaming (rapid eye movement sleep, REM) was reduced and increased awakening.[31]
Adverse drug reactions associated with propranolol therapy are similar to other lipophilic beta blockers.
Precautions and contraindications
Propranolol should be used with caution in people with:[32]
- Diabetes mellitus or hyperthyroidism, since signs and symptoms of hypoglycaemia may be masked
- Peripheral vascular disease and Raynaud's syndrome, which may be exacerbated
- Phaeochromocytoma, as hypertension may be aggravated without prior alpha blocker therapy
- Myasthenia gravis, which may be worsened
- Other drugs with bradycardic effects
Propranolol is contraindicated in patients with:[32]
- Reversible airways diseases, particularly asthma or chronic obstructive pulmonary disease (COPD)
- Bradycardia (<60 beats/minute)
- Sick sinus syndrome
- Atrioventricular block (second- or third-degree)
- Shock
- Severe hypotension
- Cocaine toxicity [per American Heart Association guidelines, 2005]
Pregnancy and lactation
Propranolol, like other beta blockers, is classified as pregnancy category C in the United States and ADEC category C in Australia. β-blocking agents in general reduce perfusion of the placenta which may lead to adverse outcomes for the neonate, including pulmonary or cardiac complications, or premature birth. The newborn may experience additional adverse effects such as hypoglycemia and bradycardia.[33]
Most β-blocking agents appear in the milk of lactating women. However, propranolol is highly bound to proteins in the bloodstream and is distributed into breast milk at very low levels.[34] These low levels are not expected to pose any risk to the breastfeeding infant, and the American Academy of Pediatrics considers propranolol therapy "generally compatible with breastfeeding".[33][34][35][36]
Interactions
Since beta blockers are known to relax the cardiac muscle and to constrict the smooth muscle, these beta-adrenergic antagonists, including propranolol, have an additive effect with other drugs which decrease blood pressure, or which decrease cardiac contractility or conductivity. Clinically significant interactions particularly occur with:[32]
- Verapamil
- Epinephrine (adrenalin)
- β2-adrenergic receptor agonists
- Salbutamol, levosalbutamol, formoterol, salmeterol, clenbuterol etc.
- Clonidine
- Ergot alkaloids
- Isoprenaline (isoproterenol)
- Nonsteroidal anti-inflammatory drugs (NSAIDs)
- Quinidine
- Cimetidine
- Lidocaine
- Phenobarbital
- Rifampicin
- Fluvoxamine (slows down the metabolism of propranolol significantly, leading to increased blood levels of propranolol)[37]
Pharmacokinetics
Propranolol is rapidly and completely absorbed, with peak plasma levels achieved about 1–3 hours after ingestion. Coadministration with food appears to enhance bioavailability.[38] Despite complete absorption, propranolol has a variable bioavailability due to extensive first-pass metabolism. Hepatic impairment therefore increases its bioavailability. The main metabolite 4-hydroxypropranolol, with a longer half-life (5.2–7.5 hours) than the parent compound (3–4 hours), is also pharmacologically active.
Propranolol is a highly lipophilic drug achieving high concentrations in the brain. The duration of action of a single oral dose is longer than the half-life and may be up to 12 hours, if the single dose is high enough (e.g., 80 mg). Effective plasma concentrations are between 10 and 100 mg/l. Toxic levels are associated with plasma concentrations above 2000 mg/l.
Mechanism of action
Propranolol is a non-selective beta blocker; that is, it blocks the action of epinephrine (adrenaline) and norepinephrine (noradrenaline) at both β1- and β2-adrenergic receptors. It has little intrinsic sympathomimetic activity, but has strong membrane stabilizing activity (only at high blood concentrations, e.g. overdose).[citation needed] Propranolol is able to cross the blood-brain-barrier and exert effects in the central nervous system in addition to its peripheral activity.[22]
In addition to blockade of adrenergic receptors, propranolol has weak inhibitory effects on the norepinephrine transporter and/or weakly stimulates norepinephrine release (i.e., the concentration of norepinephrine is increased in the synapse).[39][40] Since propranolol blocks β-adrenoceptors, the increase in synaptic norepinephrine only results in α-adrenoceptor activation, with the α1-adrenoceptor being particularly important for effects observed in animal models.[39][40] Therefore, it can be looked upon as a weak indirect α1-adrenoceptor agonist in addition to potent β-adrenoceptor antagonist.[39][40] In addition to its effects on the adrenergic system, there is evidence that indicates that propranolol may function as an antagonist of certain serotonin receptors, namely the 5-HT1A and 5-HT1B receptors.[41][42]
Both enantiomers of propranolol have a local anesthetic (topical) effect, which is normally mediated by blockade of voltage-gated sodium channels. Studies have demonstrated propranolol's ability to block cardiac, neuronal, and skeletal voltage-gated sodium channels, accounting for its known membrane stabilizing effect and antiarrhythmic and other central nervous system effects.[43][44][45]
History
Main article: Discovery and development of beta-adrenergic receptor antagonists (beta-blockers)
British scientist James W. Black developed propranolol in the 1960s.[46] In 1988, he was awarded the Nobel Prize in Medicine for this discovery. Propranolol was derived from the early β-adrenergic antagonists dichloroisoprenaline and pronethalol. The key structural modification, which was carried through to essentially all subsequent beta blockers, was the insertion of an oxymethylene group into the aryl ethanolamine structure of pronethalol, thus greatly increasing the potency of the compound. This also apparently eliminated the carcinogenicity found with pronethalol in animal models.
Newer, more cardio-selective beta blockers (such as bisoprolol, nebivolol, carvedilol, or metoprolol) are now used in the treatment of hypertension.
Society and culture
In a 1987 study by the International Conference of Symphony and Opera Musicians, 27% of interviewed members admitted to using beta blockers such as propranolol for musical performances.[47] For about 10–16% of performers, their degree of stage fright is considered pathological.[47][48] Propranolol is used by musicians, actors, and public speakers for its ability to treat anxiety symptoms activated by the sympathetic nervous system.[49] This can be seen as giving participating individuals an unfair advantage, especially in competitions, akin to the use of performance-enhancing drugs in athletes.[50]
Brand names
Original propranolol was marketed in 1965 under the brand name Inderal and manufactured by ICI Pharmaceuticals (now AstraZeneca). Propranolol is also marketed under brand names Avlocardyl, Deralin, Dociton, Inderalici, InnoPran XL, Sumial, Anaprilin, and Bedranol SR (Sandoz). In India it is marketed under brand names such as Ciplar and Ciplar LA by Cipla. Hemangeol, a 4.28 mg/mL solution of propranolol, is indicated for the treatment of proliferating infantile hemangioma.[51]
Research
In 2015, a trial in women with epithelial ovarian cancer showed that the intake of a non-selective β-blocker was associated with a longer survival compared to a β1-selective β-blocker or no β-blocker.[52] Currently, an interventional study is being conducted at the M.D. Anderson Cancer Center to access the feasibility of a non-selective β-blocker plus standard chemotherapy (paclitaxel and carboplatin or possibly docetaxel) to treat ovarian cancer.[53]
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- ^ a b Steenen, S. A.; van Wijk, A. J.; van der Heijden, G. J.; van Westrhenen, R.; de Lange, J.; de Jongh, A. (2015). "Propranolol for the treatment of anxiety disorders: Systematic review and meta-analysis". Journal of Psychopharmacology 30 (2): 128–139. doi:10.1177/0269881115612236. ISSN 0269-8811.
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- ^ https://clinicaltrials.gov/show/NCT01504126. Retrieved 17 October 2015. Missing or empty
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External links
- Stapleton MP (1997). "Sir James Black and propranolol. The role of the basic sciences in the history of cardiovascular pharmacology". Texas Heart Institute Journal 24 (4): 336–42. PMC 325477. PMID 9456487.
- U.S. National Library of Medicine: Drug Information Portal - Propranolol
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UpToDate Contents
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- 1. Treatment and prognosis of essential tremor
- 2. Treatment of acute stress disorder in adults
- 3. 幼児血管腫のマネージメント management of infantile hemangiomas
- 4. 肝硬変患者における静脈瘤出血に対する一次予防および静脈瘤形成予防 primary and pre primary prophylaxis against variceal hemorrhage in patients with cirrhosis
- 5. Pharmacotherapy for social anxiety disorder in adults
English Journal
- The inverse agonist propranolol confers no corticosteroid-sparing activity in mild-to-moderate persistent asthma.
- Anderson WJ, Short PM, Williamson PA, Manoharan A, Lipworth BJ.
- Clinical science (London, England : 1979).Clin Sci (Lond).2014 Dec;127(11):635-43. doi: 10.1042/CS20140249.
- The murine asthma model shows that switching off airway β2 receptors with an inverse agonist may confer anti-inflammatory effects as well as corticosteroid-sparing activity. We have assessed for any corticosteroid-sparing effects of propranolol, an inverse agonist, added to low-dose inhaled cortico
- PMID 24938324
- Neuropeptide AF induces anxiety-like and antidepressant-like behavior in mice.
- Palotai M1, Telegdy G2, Tanaka M3, Bagosi Z1, Jászberényi M1.
- Behavioural brain research.Behav Brain Res.2014 Nov 1;274:264-9. doi: 10.1016/j.bbr.2014.08.007. Epub 2014 Aug 10.
- Little is known about the action of neuropeptide AF (NPAF) on anxiety and depression. Only our previous study provides evidence that NPAF induces anxiety-like behavior in rats. Therefore, the aim of the present study was to investigate the action of NPAF on depression-like behavior and the underlyin
- PMID 25116251
- The Odd Sibling: Features of β3-Adrenoceptor Pharmacology.
- Cernecka H1, Sand C1, Michel MC2.
- Molecular pharmacology.Mol Pharmacol.2014 Nov;86(5):479-84. doi: 10.1124/mol.114.092817. Epub 2014 Jun 2.
- β3-Adrenoceptor agonists have recently been introduced for the treatment of overactive urinary bladder syndrome. Their target, the β3-adrenoceptor, was discovered much later than β1- and β2-adrenoceptors and exhibits unique properties which make extrapolation of findings from the other two subty
- PMID 24890609
Japanese Journal
- 症例報告 ホスホマイシンナトリウムとプロプラノロール塩酸塩の併用による膿疱型薬疹の1例
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- 臨床皮膚科 67(7), 485-489, 2013-06
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- A Novel Method for Synthesis of Chiral Polymer Useful for Membrane Application
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- Polymer journal 41(12), 1067-1075, 2009-12-15
- NAID 10026363008
- A Novel Osmotic Pump Tablet Using Core of Drug-resin Complexes for Time-controlled Delivery System
- Wang Chao,Chen Fei,Li Ji-zhong [他],TANG Hai,LI Xiang,YAN Ke-shu,YE Guan-hao,PAN Wei-san
- 藥學雜誌 128(5), 773-782, 2008-05-01
- … The system uses the core of drug-resin complexes (DRCs) loaded with propranolol hydrochloride (PNH) for time-controlled delivery. …
- NAID 110006668274
Related Links
- propranolol hydrochloride [-pran′əlol] a nonselective beta-adrenergic receptor blocking agent. indications It is prescribed in the treatment of hypertension, angina pectoris, catecholamine-induced cardiac arrhythmias ...
- Sigma-Aldrich offers Sigma-P0884, (±)-Propranolol hydrochloride for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Biochem/physiol Actions β-adrenoceptor ...
Related Pictures
★リンクテーブル★
| リンク元 | 「プロプラノロール」 |
| 関連記事 | 「hydrochloride」 |
「プロプラノロール」
- 英
- propranolol
- ラ
- propranololum
- 化
- 塩酸プロプラノロール propranolol hydrochloride
- 商
- アイデイトロール、インデラル Inderal、サワタール、ソラシロール、ノルモテンス、ヘルツベース、メントリース
- 関
- 血圧降下剤
- 非選択的β受容体遮断薬 (β1受容体＝β2受容体)
- 競合的
- 内因性交感神経刺激作用：無
- 膜安定化作用：有
- 脳血管関門：通過
- レニン分泌抑制作用：有
- 降圧作用を示す
- 作用
- 抗狭心作用
- 抗不整脈作用