マレイン酸クロルフェニラミン、クロルフェニラミンマレイン酸塩
- 関
- Chlor-Trimeton、chlorphenamine、chlorpheniramine、chlorpheniramine polistirex、d-chlorpheniramine maleate
WordNet
- a salt or ester of maleic acid; used as a nontricyclic antidepressant drug for psychomotor activation
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/19 22:00:31」(JST)
wiki en
| Systematic (IUPAC) name | |
|---|---|
|
3-(4-chlorophenyl)-N,N-dimethyl-
3-pyridin-2-yl-propan-1-amine |
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| Clinical data | |
| Trade names | Chlor-trimeton |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682543 |
| Pregnancy category |
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| Legal status |
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| Routes of administration |
Oral, IV, IM, SC |
| Pharmacokinetic data | |
| Bioavailability | 25 to 50% |
| Protein binding | 72% |
| Metabolism | Hepatic (CYP2D6) |
| Biological half-life | 21–27 hours |
| Excretion | Renal |
| Identifiers | |
| CAS Registry Number | 113-92-8 N |
| ATC code | R06AB04 |
| PubChem | CID: 2725 |
| IUPHAR/BPS | 1210 |
| DrugBank | DB01114 Y |
| ChemSpider | 2624 Y |
| UNII | 3U6IO1965U Y |
| KEGG | D07398 Y |
| ChEBI | CHEBI:52010 Y |
| ChEMBL | CHEMBL505 Y |
| Chemical data | |
| Formula | C16H19ClN2 |
| Molecular mass | 274.788 g/mol |
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SMILES
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InChI
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| Physical data | |
| Solubility in water | 0.55 g/100 mL, liquid mg/mL (20 °C) |
| N (what is this?) (verify) | |
Chlorphenamine (INN), chlorpheniramine (USAN, former BAN) or piriton (trade name), commonly marketed in the form of chlorpheniramine maleate (Chlorphen-12[1]), is a first-generation alkylamine antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria. Its sedative effects are relatively weak compared to other first-generation antihistamines. Chlorphenamine is one of the most commonly used antihistamines in small-animal veterinary practice. Although not generally approved as an antidepressant or anti-anxiety medication, chlorphenamine appears to have these properties as well.[2][3]
Chlorphenamine is part of a series of antihistamines including pheniramine (Naphcon) and its halogenated derivatives and others including fluorpheniramine, dexchlorpheniramine (Polaramine), brompheniramine (Dimetapp), dexbrompheniramine (Drixoral), deschlorpheniramine, dipheniramine (also known as triprolidine with the trade name Actifed), and iodopheniramine.
The halogenated alkylamine antihistamines all exhibit optical isomerism, and chlorphenamine in the indicated products is racemic chlorphenamine maleate, whereas dexchlorpheniramine is the dextrorotary stereoisomer.
Contents
- 1 Serotonergic and norepinephrinergic effects
- 2 Combination medications
- 3 Adverse effects
- 4 Synthesis
- 5 See also
- 6 References
Serotonergic and norepinephrinergic effects
In addition to being an histamine H1 receptor antagonist, chlorphenamine has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI.[4] A similar antihistamine, brompheniramine, led to the discovery of the SSRI zimelidine. Limited clinical evidence shows that it is comparable to several antidepressant medications in its ability to inhibit the reuptake of serotonin and also norepinephrine (noradrenaline).[5]
A study performed on Fischer 344/Brown Norway F1 hybrid rats showed that intraventricular administration of chlorphenamine reduced fear-related behaviors and improved maze performance. It was also noted that long-term administration of chlorphenamine reduced age-related deficits in motor function.[6]
Combination medications
Chlorphenamine is often combined with phenylpropanolamine to form an allergy medication with both antihistamine and decongestant properties, though phenylpropanolamine is no longer available in the US after studies showed it increased the risk of stroke in young women. Chlorpheniramine remains available with no such risk. Brand names had included Demazin, Allerest 12 Hour, Codral Nighttime, Chlornade, Contac 12 Hour, Exchange Select Allergy Multi-Symptom, A. R. M. Allergy Relief, Ordrine, Ornade Spansules, Teldrin, Triaminic, and Tylenol Cold/Allergy.
Chlorphenamine is combined with a narcotic (hydrocodone) in the product Tussionex, which is indicated for treatment of cough and upper respiratory symptoms associated with allergy or cold in adults and children 6 years of age and older.[7] This combination is manufactured as a time-released formula, which allows for administration every 12 hours, versus the more common 4-to-6-hour regimen for other narcotic cough suppressants.
Chlorphenamine/dihydrocodeine immediate-release syrups are also marketed. The antihistamine is helpful in cases where allergy or common cold is the reason for the cough; it is also a potentiator of opioids, allowing enhanced suppression of cough, analgesia, and other effects from a given quantity of the drug by itself. In various places in the world, cough & cold preparations containing codeine and chlorphenamine are available.
In the drug Coricidin, chlorphenamine is combined with the cough suppressant dextromethorphan.
Adverse effects
The adverse effects include drowsiness, dizziness, confusion, constipation, anxiety, nausea, blurred vision, restlessness, decreased coordination, dry mouth, shallow breathing, hallucinations, irritability, problems with memory or concentration, tinnitus and trouble urinating.
A large study linked the development of Alzheimer's disease and other forms of dementia to the use of chlorpheniramine and other first-generation antihistamines, due to their anticholinergic properties. [8]
Synthesis
Chlorphenamine, 3-(p-chlorophenyl)-3-(2-pyridyl)propyldimethylamine, is synthesized in two ways. The first is from 4-chlorbenzylcyanide, which is reacted with 2-chloropyridine in the presence of sodium amide to form 4-chlorophenyl(2-pyridyl)acetonitrile. Alkylating this with 2-dimethylaminoethylchloride in the presence of sodium amide gives γ-(4-chlorphenyl)-γ-cyano-N,N-dimethyl-2-pyridinepropanamine, the hydrolysis and decarboxylation of which lead to chlorphenamine.
Chlorpheniramine synthesis 1: D. Papa, E. Schwenk, N. Sperber, U.S. Patent 2,567,245 (1951).
The second way is from pyridine, which undergoes alkylation by 4-chlorobenzylchloride,[9]
giving 2-(4-chlorobenzyl)pyridine. Alkylating this with 2-dimethylaminoethylchloride in the presence of sodium amide gives chlorphenamine.
Chlorpheniramine synthesis 2: D. Papa, E. Schwenk, N. Sperber, U.S. Patent 2,676,964 (1954).
See also
- Diphenhydramine
- Dextromethorphan
- Tripelennamine
References
- ^ "Chlorphen-12".
- ^ Carlsson, Arvid; Lindqvist, Margit. "Central and peripheral monoaminergic membrane-pump blockade by some addictive analgesics and antihistamines". Journal of Pharmacy and Pharmacology. Journal of Pharmacy and Pharmacology. Retrieved 1 December 2013.
- ^ Gruetter CA, Lemke SM, Anestis DK, Szarek JL, Valentovic MA. "Potentiation of 5-hydroxytryptamine-induced contraction in rat aorta by chlorpheniramine, citalopram and fluoxetine". Department of Pharmacology, Marshall University School of Medicine, Huntington, WV. PMID 1358631. Retrieved 1 December 2013.
- ^ Carlsson, A.; Linqvist M. (1969). "Central and peripheral monoaminergic membrane-pump blockade by some addictive analgesics and antihistamines". Journal of Pharmacy and Pharmacology 21 (7): 460–464. doi:10.1111/j.2042-7158.1969.tb08287.x. PMID 4390069.
- ^ Hellbom, E. (2006). "Chlorpheniramine, selective serotonin-reuptake inhibitors (SSRIs) and over-the-counter (OTC) treatment". Medical Hypotheses 66 (4): 689–690. doi:10.1016/j.mehy.2005.12.006. PMID 16413139.
- ^ Hasenöhrl, R. U.; Weth, K.; Huston, J. P. (1999). "Intraventricular infusion of the histamine H1 receptor antagonist chlorpheniramine improves maze performance and has anxiolytic-like effects in aged hybrid Fischer 344×Brown Norway rats". Experimental Brain Research 128 (4): 435–440. doi:10.1007/s002210050866. PMID 10541737.
- ^ "Tussionex® Pennkinetic® (hydrocodone polistirex and chlorpheniramine polistirex) Extended-Release Suspension" (PDF). UCB. 2011.
- ^ Gray, Shelly L.; Anderson, Melissa L.; Dublin, Sascha; Hanlon, Joseph T.; Hubbard, Rebecca; Walker, Rod; Yu, Onchee; Crane, Paul K.; Larson, Eric B. (January 26, 2015). "Cumulative Use of Strong Anticholinergics and Incident Dementia: A Prospective Cohort Study". JAMA Intern. Med. 175 (3): 401–7. doi:10.1001/jamainternmed.2014.7663. PMC 4358759. PMID 25621434. Retrieved January 27, 2015.
- ^ Djerassi, Carl (1948). "Brominations with Pyridine Hydrobromide Perbromide". Journal of the American Chemical Society 70 (1): 417–418. doi:10.1021/ja01181a508. edit
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UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
- 1. アレルギー性鼻炎の薬物療法 pharmacotherapy of allergic rhinitis
- 2. デキストロメトルファン中毒：治療 dextromethorphan poisoning treatment
- 3. デキストロメトルファン乱用および中毒：臨床的特徴および診断 dextromethorphan abuse and poisoning clinical features and diagnosis
- 4. 妊娠中のアレルギー疾患の認識およびマネージメント recognition and management of allergic disease during pregnancy
- 5. OTC咳止め・かぜ薬：小児の中毒へのアプローチ over the counter cough and cold preparations approach to pediatric poisoning
English Journal
- H(1)-histamine receptors in the amygdala are involved in emotional memory but do not mediate anxiety-related behaviors in mice submitted to EPM testing.
- Serafim KR, Gianlorenço AC, Daher FP, Mattioli R.SourceLaboratory of Neuroscience, Physiotherapy Department, Center of Biological Sciences and Health, Federal University of Sao Carlos, Rod. Washington Luis, Sao Carlos, Brazil. Kelly.serafim@hotmail.com
- Brain research bulletin.Brain Res Bull.2012 Oct 1;89(1-2):1-7. doi: 10.1016/j.brainresbull.2012.06.009. Epub 2012 Jul 6.
- This study investigated the role of amygdala H(1) receptors in state-dependent memory deficits induced by l-histidine (LH). Tests using an elevated plus-maze (EPM) were performed on two consecutive days: Trial 1 (T1) and Trial 2 (T2). Before each trial, mice were intraperitoneally (IP) injected with
- PMID 22772356
- Inhibitory effect of Zataria multiflora Boiss and carvacrol on histamine (H(1) ) receptors of guinea-pig tracheal chains.
- Boskabady MH, Tabanfar H, Gholamnezhad Z, Sadeghnia HR.SourceDepartment of Physiology and Pharmaceutical Research Centre, Medical School, Mashhad University of Medical Sciences, Mashhad, Iran Department of Pharmacology and Pharmacology Research Centre of Medicinal Plants, Medical School, Mashhad University of Medical Sciences, Mashhad, Iran.
- Fundamental & clinical pharmacology.Fundam Clin Pharmacol.2012 Oct;26(5):609-20. doi: 10.1111/j.1472-8206.2011.00971.x. Epub 2011 Aug 1.
- The inhibitory effect of aqueous-ethanolic extract of Zataria multiflora Boiss (Labiatae) and carvacrol on histamine (H(1) ) receptors was examined on tracheal chains of guinea-pigs. The effects of three concentrations of aqueous-ethanolic extract, carvacrol, 10 nm chlorpheniramine, and saline on
- PMID 21806678
Japanese Journal
- Multivariate Optimization and Validation of a Capillary Electrophoresis Method for the Simultaneous Determination of Dextromethorphan Hydrobromur, Phenylephrine Hydrochloride, Paracetamol and Chlorpheniramine Maleate in a Pharmaceutical Preparation Using Response Surface Methodology
- PALABIYIK I. Murat,ONUR Feyyaz
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 26(8), 853-859, 2010-08-10
- NAID 10026784731
- Chemometric optimization of sequential injection spectrophotometric method for chlorpheniramine determination in pharmaceutical formulations
- Ibrahim Atta E. E.,Saleh Tawfik A.,Abulkibash A. M. [他]
- Journal of flow injection analysis 27(1), 26-31, 2010-06
- NAID 40017234990
Related Links
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★リンクテーブル★
| リンク元 | 「クロルフェニラミン」「クロルフェナミン」「Chlor-Trimeton」「chlorpheniramine polistirex」「クロルフェニラミンマレイン酸塩」 |
| 拡張検索 | 「d-chlorpheniramine maleate」 |
| 関連記事 | 「maleate」「chlorpheniramine」 |
「クロルフェニラミン」
- 英
- chlorpheniramine
- 化
- マレイン酸クロルフェニラミン chlorpheniramine maleate、クロルフェニラミンマレイン酸塩
- 商
- クロダミン、LL配合、アストーマ、アニミング、アレルギン、エンペラシン、クロール・トリメトン Chlor-Trimeton、クロフェドリン、サクコルチン、セレスターナ、セレスタミン、ニチコデ、ネオアムノール、ネオマレルミン、ネオレスタール、ネオレスタミン、ヒスタール、ヒスタブロック、ビスミラー、フェニラミン、フスコデ、フスコブロン、フステン、プラコデ、プラデスミン、ベタセレミン、ペレックス、ポラジット、ポララミン、マゴチミン、ミゼロン、ムコブロチン、ライトゲン
- 関
- クロルフェナミン
- 抗ヒスタミン剤
- 古典的抗ヒスタミン薬
- アルキルアミン系。ヒスタミンH1受容体拮抗作用。
- 作用d体>>l体
- エタノールアミン系のジフェンヒドラミンより中枢神経作用が弱い
「クロルフェナミン」
「Chlor-Trimeton」
「chlorpheniramine polistirex」
クロルフェニラミン・リスチレクス
「クロルフェニラミンマレイン酸塩」
「d-chlorpheniramine maleate」
d-マレイン酸クロルフェニラミン、d-クロルフェニラミンマレイン酸塩
「maleate」