メタコリン
WordNet
- parasympathomimetic drug (trademark Mecholyl) that stimulates secretions and smooth muscle activity (同)Mecholyl
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/04/19 22:56:59」(JST)
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Methacholine
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Systematic (IUPAC) name |
2-(Acetyloxy)-N,N,N-trimethylpropan-1-aminium |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
? |
Identifiers |
CAS number |
55-92-5 N
62-51-1 (chloride) |
ATC code |
None |
PubChem |
CID 6114 |
DrugBank |
DB06709 |
ChemSpider |
5888 Y |
UNII |
03V657ZD3V Y |
KEGG |
D04970 Y |
ChEBI |
CHEBI:50142 Y |
ChEMBL |
CHEMBL978 N |
Chemical data |
Formula |
C8H18NO2+ |
Mol. mass |
160.234 g/mol |
SMILES
- [Cl-].O=C(OC(C)C[N+](C)(C)C)C
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InChI
-
InChI=1S/C8H18NO2.ClH/c1-7(11-8(2)10)6-9(3,4)5;/h7H,6H2,1-5H3;1H/q+1;/p-1 Y
Key:JHPHVAVFUYTVCL-UHFFFAOYSA-M Y
|
N (what is this?) (verify) |
Methacholine (Provocholine) is a synthetic choline ester that acts as a non-selective muscarinic receptor agonist in the parasympathetic nervous system.
Contents
- 1 Uses
- 2 Pharmacology
- 3 Contraindications
- 4 References
- 5 External links
Uses
Methacholine is primarily used to diagnose bronchial hyperreactivity,[1] which is the hallmark of asthma and also occurs in chronic obstructive pulmonary disease. This is accomplished through the bronchial challenge test, or methacholine challenge, in which a subject inhales aerosolized methacholine, leading to bronchoconstriction. Other therapeutic uses are limited by its adverse cardiovascular effects, such as bradycardia and hypotension, which arise from its function as a cholinomimetic.
Pharmacology
It is highly active at all of the muscarinic receptors, but has little effect on the nicotinic receptors. Methacholine has a charged quaternary amine structure, rendering it insoluble to lipid cell membranes. Clinically, this means that it will not cross the blood–brain barrier and has poor absorption from the gastrointestinal tract. It is broken down at a relatively slow rate within the body, due to its resistance to acetylcholinesterases.
Methacholine has a β-methyl group which provides selectivity towards muscarinic receptors as compared to nicotinic receptors. The quaternary ammonium group is essential for activity. The ester however makes it susceptible to the enzyme acetylcholine esterase.[2]
Contraindications
Use of methacholine is contraindicated in patients with recent heart attack or stroke, uncontrolled hypertension, known severe airway disease, or an aortic aneurysm. It may be used with caution by nursing or pregnant mothers and patients taking certain medications for myasthenia gravis.[3]
References
- ^ Birnbaum S, Barreiro TJ (June 2007). "Methacholine challenge testing: identifying its diagnostic role, testing, coding, and reimbursement". Chest 131 (6): 1932–5. doi:10.1378/chest.06-1385. PMID 17565027.
- ^ Medicinal Chemistry of Adrenergics and Cholinergics
- ^ Valentin Popa (2001). "ATS guidelines for methacholine and exercise challenge testing". American Journal of Respiratory and Critical Care Medicine 163 (1): 292–293. doi:10.1164/ajrccm.163.1.16310b.
External links
Cholinergics
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Receptor ligands
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mAChR
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- Agonists: 77-LH-28-1
- AC-42
- AC-260,584
- Aceclidine
- Acetylcholine
- AF30
- AF150(S)
- AF267B
- AFDX-384
- Alvameline
- AQRA-741
- Arecoline
- Bethanechol
- Butyrylcholine
- Carbachol
- CDD-0034
- CDD-0078
- CDD-0097
- CDD-0098
- CDD-0102
- Cevimeline
- Choline
- cis-Dioxolane
- Ethoxysebacylcholine
- LY-593,039
- L-689,660
- LY-2,033,298
- McNA343
- Methacholine
- Milameline
- Muscarine
- NGX-267
- Ocvimeline
- Oxotremorine
- PD-151,832
- Pilocarpine
- RS86
- Sabcomeline
- SDZ 210-086
- Sebacylcholine
- Suberylcholine
- Talsaclidine
- Tazomeline
- Thiopilocarpine
- Vedaclidine
- VU-0029767
- VU-0090157
- VU-0152099
- VU-0152100
- VU-0238429
- WAY-132,983
- Xanomeline
- YM-796
Antagonists: 3-Quinuclidinyl Benzilate
- 4-DAMP
- Aclidinium Bromide
- Anisodamine
- Anisodine
- Atropine
- Atropine Methonitrate
- Benactyzine
- Benzatropine/Benztropine
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine/Dicycloverine
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine/Ethylbenztropine
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba Toxin 3
- Mamba Toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-Piperidyl Benzilate
- N-Methyl-3-Piperidyl Benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine/Hyoscine
- Solifenacin
- Telenzepine
- Tiotropium bromide
- Tolterodine
- Trihexyphenidyl
- Tripitamine
- Tropatepine
- Tropicamide
- WIN-2299
- Xanomeline
- Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine
- chlorphenamine
- cyproheptadine
- dimenhydrinate
- diphenhydramine
- doxylamine
- mepyramine/pyrilamine
- phenindamine
- pheniramine
- tripelennamine
- triprolidine, etc)
- Tricyclic Antidepressants (Amitriptyline
- doxepin
- trimipramine, etc)
- Tetracyclic Antidepressants (Amoxapine
- maprotiline, etc)
- Typical Antipsychotics (Chlorpromazine
- thioridazine, etc)
- Atypical Antipsychotics (Clozapine
- olanzapine, etc.)
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nAChR
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- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Lobeline
- MEM-63,908/RG-3487
- Nicotine
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- RJR-2429
- Sazetidine A
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberylcholine
- Suxamethonium/Succinylcholine
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
Antagonists: 18-Methoxycoronaridine
- α-Bungarotoxin
- α-Conotoxin
- Alcuronium
- Amantadine
- Anatruxonium
- Atracurium
- Bupropion
- Chandonium
- Chlorisondamine
- Cisatracurium
- Coclaurine
- Coronaridine
- Dacuronium
- Decamethonium
- Dextromethorphan
- Dextropropoxyphene
- Dextrorphan
- Diadonium
- DHβE
- Dihydrochandonium
- Dimethyltubocurarine/Metocurine
- Dipyrandium
- Dizocilpine/MK-801
- Doxacurium
- Esketamine
- Fazadinium
- Gallamine
- Hexafluronium
- Hexamethonium/Benzohexonium
- Ibogaine
- Isoflurane
- Ketamine
- Kynurenic acid
- Laudexium/Laudolissin
- Levacetylmethadol
- Malouetine
- Mecamylamine
- Memantine
- Methadone (Levomethadone)
- Methorphan/Racemethorphan
- Methyllycaconitine
- Metocurine
- Mivacurium
- Morphanol/Racemorphan
- Neramexane
- Nitrous Oxide
- Pancuronium
- Pempidine
- Pentamine
- Pentolinium
- Phencyclidine
- Pipecuronium
- Radafaxine
- Rapacuronium
- Rocuronium
- Surugatoxin
- Thiocolchicoside
- Toxiferine
- Trimethaphan
- Tropeinium
- Tubocurarine
- Vecuronium
- Xenon
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Reuptake inhibitors
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Plasmalemmal
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CHT Inhibitors
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- Hemicholinium-3/Hemicholine
- Triethylcholine
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Vesicular
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Enzyme inhibitors
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Anabolism
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ChAT inhibitors
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- 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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Catabolism
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AChE inhibitors
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BChE inhibitors
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- Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.
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Others
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Precursors
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- Choline (Lecithin)
- Citicoline
- Cyprodenate
- Dimethylethanolamine
- Glycerophosphocholine
- Meclofenoxate/Centrophenoxine
- Phosphatidylcholine
- Phosphatidylethanolamine
- Phosphorylcholine
- Pirisudanol
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Cofactors
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- Acetic acid
- Acetylcarnitine
- Acetyl-coA
- Vitamin B5 (Pantethine
- Pantetheine
- Panthenol)
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Others
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- Acetylcholine releasing agents: α-Latrotoxin
- β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime
- Obidoxime
- Pralidoxime
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UpToDate Contents
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English Journal
- Pharmacologic inhibition of S-nitrosoglutathione reductase protects against experimental asthma in BALB/c mice through attenuation of both bronchoconstriction and inflammation.
- Blonder JP, Mutka SC, Sun X, Qiu J, Green LH, Mehra NK, Boyanapalli R, Suniga M, Look K, Delany C, Richards JP, Looker D, Scoggin C, Rosenthal GJ.AbstractBACKGROUND: S-nitrosoglutathione (GSNO) serves as a reservoir for nitric oxide (NO) and thus is a key homeostatic regulator of airway smooth muscle tone and inflammation. Decreased levels of GSNO in the lungs of asthmatics have been attributed to increased GSNO catabolism via GSNO reductase (GSNOR) leading to loss of GSNO- and NO- mediated bronchodilatory and anti-inflammatory actions. GSNOR inhibition with the novel small molecule, N6022, was explored as a therapeutic approach in an experimental model of asthma.
- BMC pulmonary medicine.BMC Pulm Med.2014 Jan 10;14(1):3. [Epub ahead of print]
- BACKGROUND: S-nitrosoglutathione (GSNO) serves as a reservoir for nitric oxide (NO) and thus is a key homeostatic regulator of airway smooth muscle tone and inflammation. Decreased levels of GSNO in the lungs of asthmatics have been attributed to increased GSNO catabolism via GSNO reductase (GSNOR)
- PMID 24405692
- Predictors of neutrophilic airway inflammation in young smokers with asthma.
- Westergaard C, Munck C, Helby J, Porsbjerg C, Hansen L, Backer V.Author information Respiratory Research Unit, Bispebjerg University Hospital, Copenhagen, Denmark.AbstractIntroduction: Asthma is one of the most widespread chronic diseases worldwide. In spite of numerous detrimental effects on asthma, smoking is common among asthma patients. These smoking-induced aggravations of asthma may be attributed to changes in airway inflammation, which is characterized by a higher degree of neutrophilic inflammation than in non-smokers. A state of neutrophilic inflammation may lead to increased steroid resistance and an accelerated loss of lung function owing to tissue destruction. The aim of the present study was to elucidate predictors of neutrophilic inflammation in young asthmatic smokers not on steroid treatment, including analysis of tobacco history and bacterial colonization. Methods: In a cross-sectional study, 52 steroid-free, current smokers with asthma were examined with induced sputum, fractional exhaled nitric oxide (FeNO), lung function, ACQ6 score, mannitol and methacholine challenge. A sample from the sputum induction was taken for bacterial analysis using 16S gene PCR technique and sequencing. Results: Using one-way ANOVA and binary and linear regression models, only age and ACQ6 score were found to be significant predictors for airway neutrophilia. The investigation also included analysis for effect of pack years, current tobacco consumption, body mass index, lung function, FeNO; methacholine and mannitol responsiveness, atopy, gender, asthma history and presence of bacteria. The most common potentially pathogenic bacteria found were Streptococcus spp., Haemophilus spp. and Mycoplasma spp. Conclusion: In the present study, no tobacco related predictors of airway neutrophilia were found, indicating that in the younger years of asthma patients who smoke, the amount of tobacco smoked in life does not influence the degree of neutrophilia. Conversely, for asthmatic smokers neutrophilia may be induced when a certain threshold of tobacco consumption is reached.
- The Journal of asthma : official journal of the Association for the Care of Asthma.J Asthma.2014 Jan 10. [Epub ahead of print]
- Introduction: Asthma is one of the most widespread chronic diseases worldwide. In spite of numerous detrimental effects on asthma, smoking is common among asthma patients. These smoking-induced aggravations of asthma may be attributed to changes in airway inflammation, which is characterized by a hi
- PMID 24404796
- Eosinophilic airway inflammation and airway hyperresponsiveness according to aeroallergen sensitization pattern in patients with lower airway symptoms.
- Jo EJ1, Kim MY2, Lee SE1, Lee SY2, Kim MH2, Song WJ2, Kim SH1, Kang HR2, Chang YS1, Cho SH2, Min KU2.Author information 1Department of Internal Medicine, Seoul National University College of Medicine, Seoul, Korea. ; Institute of Allergy and Clinical Immunology, Seoul National University Medical Research Center, Seoul, Korea. ; Department of Internal Medicine, Seoul National University Bundang Hospital, Seongnam, Korea.2Department of Internal Medicine, Seoul National University College of Medicine, Seoul, Korea. ; Institute of Allergy and Clinical Immunology, Seoul National University Medical Research Center, Seoul, Korea.AbstractPURPOSE: Sensitization to specific allergens may be important in the development of allergic airway inflammation and airway hyperresponsiveness (AHR). We evaluated the effect of specific aeroallergen sensitization on eosinophilic airway inflammation and AHR.
- Allergy, asthma & immunology research.Allergy Asthma Immunol Res.2014 Jan;6(1):39-46. doi: 10.4168/aair.2014.6.1.39. Epub 2013 Oct 30.
- PURPOSE: Sensitization to specific allergens may be important in the development of allergic airway inflammation and airway hyperresponsiveness (AHR). We evaluated the effect of specific aeroallergen sensitization on eosinophilic airway inflammation and AHR.METHODS: We reviewed retrospectively the c
- PMID 24404392
Japanese Journal
- Alleviation of OVA-Induced Airway Inflammation by Flowers of Inula japonica in a Murine Model of Asthma
- PARK Young Na,LEE Youn Ju,CHOI Jeon Hyeun,JIN Meihua,YANG Ju Hae,LI Ying,LEE Jiean,LI Xian,KIM Keuk-Jun,SON Jong Keun,CHANG Hyeun Wook,KIM Jong Yeon,LEE Eunkyung
- Bioscience, biotechnology, and biochemistry 75(5), 871-876, 2011-05-23
- … IFE also suppressed AHR induced by aerosolized methacholine in OVA-induced mice. …
- NAID 10028272455
- Plasma substance p levels in patients with persistent cough.
- Otsuka Kojiro,Niimi Akio,Matsumoto Hisako,Ito Isao,Yamaguchi Masafumi,Matsuoka Hirofumi,Jinnai Makiko,Oguma Tsuyoshi,Takeda Tomoshi,Nakaji Hitoshi,Chin Kazuo,Sasaki Kazuhiko,Aoyama Norihito,Mishima Michiaki
- Respiration; international review of thoracic diseases 82(5), 431-438, 2011
- … Correlations were evaluated between plasma SP levels as measured with ELISA and methacholine airway hyperresponsiveness (airway sensitivity and airway reactivity), capsaicin cough sensitivity, sputum eosinophil and neutrophil counts, and pulmonary function. … Plasma SP levels correlated with airway sensitivity (threshold dose of methacholine) in the patients with asthmatic cough (r = -0.37, p = 0.005) but not with airway reactivity, cough sensitivity, FEV(1) values, or sputum eosinophil and neutrophil counts in either group. …
- NAID 120003534358
- Airway wall structure assessed by endobronchial ultrasonography and bronchial hyperresponsiveness in patients with asthma
- Kita Toshiyuki,Fujimura Masaki,Sone Takashi,Inuzuka Kanako,Myou Shigeharu,Nakao Shinji
- Journal of Bronchology 17(4), 301-306, 2010-10
- … We measured bronchial hyperresponsiveness to methacholine [the provocative concentration of methacholine causing a decrease of 20% or more in forced expiratory volume in 1 s (PC20)]. …
- NAID 120002772010
Related Links
- Methacholine is primarily used to diagnose bronchial hyperreactivity, which is the hallmark of asthma and also occurs in chronic obstructive pulmonary disease. This is accomplished through the bronchial challenge test, or methacholine ...
- The patient breathes in nebulized methacholine or histamine. Thus the test may also be called a methacholine challenge test or histamine challenge test respectively. Both drugs provoke bronchoconstriction, or narrowing of the airways .
Related Pictures
★リンクテーブル★
[★]
- 英
- methacholine
- 同
- メサコリン
- 化
- 塩化メタコリン, methacholine chloride、臭化メタコリン, methacholine bromide
- 関
[show details]
[★]
メタコリン、塩化メタコリン