brompheniramine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/28 10:08:28」(JST)

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Brompheniramine

Systematic (IUPAC) name
3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682545
Pregnancy cat.	C (USA)
Legal status	Unscheduled, OTC
Routes	Oral
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half-life	24.9 ± 9.3 hours
Excretion	Urine
Identifiers
CAS number	86-22-6
ATC code	R06AB01
PubChem	CID 6834
DrugBank	DB00835
ChemSpider	6573 Y
UNII	H57G17P2FN Y
KEGG	D07543 Y
ChEBI	CHEBI:3183 Y
ChEMBL	CHEMBL811 Y
Chemical data
Formula	C16H19BrN2
Mol. mass	319.24 g/mol
SMILES Brc1ccc(cc1)C(c2ncccc2)CCN(C)C
InChI InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3 Y Key:ZDIGNSYAACHWNL-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Brompheniramine (Bromfed, Dimetapp, Bromfenex, Dimetane, BPN, Lodrane), commonly marketed as its salt brompheniramine maleate, is an antihistamine drug of the propylamine (alkylamine) class. It is readily available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine.

Brompheniramine is part of a series of antihistamines including pheniramine (Naphcon) and its halogenated derivatives and others including fluorpheniramine, chlorpheniramine, dexchlorpheniramine (Polaramine), deschlorpheniramine, dipheniramine (also known as triprolidine with the trade name Actifed), and iodopheniramine.

The halogenated alkylamine antihistamines all exhibit optical isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

Brompheniramine has antidepressant properties, inhibiting reuptake of the neurotransmitter serotonin. Based on this knowledge, Arvid Carlsson and his colleagues, working at the Swedish company Astra AB, were able to derive the first marketed selective serotonin reuptake inhibitor, zimelidine, from brompheniramine.

Like other agents of this type, brompheniramine also has analgesic-sparing (potentiating) effects on opioid analgesics, commonly reducing codeine, dihydrocodeine, and hydrocodone requirements by 10 to 35 percent.

Pharmacology

Brompheniramine works by acting as an antagonist of histamine H₁ receptors. It also functions as a moderately effective anticholinergic agent, and is likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine.

Brompheniramine is metabolised by cytochrome P450s.

The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racaemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

Side effects

Its effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.

Chemistry

Brompheniramine, 3-(p-bromophenyl)-3-(2-pyridyl)propyldimethylamine, is an analog of chlorpheniramine. The only difference is that the chlorine atom in the benzene ring is replaced with a bromine atom. It is also synthesized in an analogous manner.

• L.A. Walter, U.S. Patent 3,061,517 (1962).
• L.A. Walter, U.S. Patent 3,030,371 (1962).

References

External links

• Rx-List.com - Brompheniramine
• Drugs.com - Brompheniramine
• NIH - Brompheniramine

UpToDate Contents

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• 1. 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
• 2. アレルギー性鼻炎の薬物療法 pharmacotherapy of allergic rhinitis
• 3. 成人における亜急性および慢性咳嗽の治療 treatment of subacute and chronic cough in adults
• 4. 患者教育：アレルギー性鼻炎（季節性アレルギー）（詳細） allergic rhinitis seasonal allergies beyond the basics

English Journal

• Safety Profile of Cough and Cold Medication Use in Pediatrics.

• Green JL1, Wang GS2, Reynolds KM3, Banner W4, Bond GR5, Kauffman RE6, Palmer RB3, Paul IM7,8, Dart RC3.
• Pediatrics.Pediatrics.2017 Jun;139(6). pii: e20163070. doi: 10.1542/peds.2016-3070. Epub 2017 May 4.
• PMID 28562262

• Brompheniramine as a novel probe for indirect UV detection and its application for the capillary electrophoresis of adamantane drugs.

• Prapatpong P1, Prutthiwanasan B1, Nuchtavorn N1, Buranaphalin S1, Suntornsuk L1.
• Journal of separation science.J Sep Sci.2017 Mar;40(5):1184-1192. doi: 10.1002/jssc.201601162. Epub 2017 Feb 7.
• PMID 28087893

• Chiral separation of brompheniramine enantiomers by recycling high-speed countercurrent chromatography using carboxymethyl-β-cyclodextrin as a chiral selector.

• Zhang P1, Xie X1, Tang K1, Xu W1.
• Journal of separation science.J Sep Sci.2016 Jun;39(12):2300-6. doi: 10.1002/jssc.201501240. Epub 2016 Jun 2.
• PMID 27080368

Japanese Journal

• Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases

• Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 804(1), 19-24, 2004-05-05
• NAID 10016548912

• The impact of donor chemical overdose on the outcome of liver transplantation

• 日本外科学会雑誌 103(臨時増刊), 606, 2002-03-10
• NAID 110003951464

• Involvement of Calmodulin Inhibition in Analgesia Induced With Low Doses of Intrathecal Trifluoperazine

• The Japanese journal of pharmacology 88(2), 151-157, 2002-02-01
• NAID 130000078265

Related Pictures

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★リンクテーブル★

リンク元	「ブロムフェニラミン」「dimetapp」
拡張検索	「dexbrompheniramine」

「ブロムフェニラミン」

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英

brompheniramine

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Dimetapp, Bromphen

「dimetapp」

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brompheniramine

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loratadine

「dexbrompheniramine」

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