関: flavoxate hydrochloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/08 03:16:12」(JST)

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Flavoxate is an anticholinergic with antimuscarinic effects. Its muscle relaxant properties may be due to a direct action on the smooth muscle rather than by antagonizing muscarinic receptors.

Clinical uses

Flavoxate is used to treat urinary bladder spasms. It is available under the trade name Urispas (Paladin),Genurin (by Recordati, Italy) in Italy and KSA,Uritac by El Saad company in Syria, under the name Bladderon by Nippon Shinyaku of Japan, or Bladuril in Chile.

Flavoxate is indicated for symptomatic relief of interstitial cystitis, dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis.

Side effects

Flavoxate is generally well tolerated, but can potentially cause, vomiting, upset stomach, dry mouth or throat, blurred vision, eye pain,^[1] and increased sensitivity of your eyes to light.

Contraindications

Flavoxate is contraindicated in patients who have any of the following obstructive conditions: pyloric or duodenal obstruction, obstructive intestinal lesions or ileus, achalasia, gastrointestinal hemorrhage and obstructive uropathies of the lower urinary tract.

Synthesis

Smooth muscle relaxant. Prepn of the hydrochloride:^[2] P. Da Re, U.S. Patent 2,921,070 and U.S. Patent 3,350,411 (1960 to Recordati and 1967 to Seceph).

Nitration of hydroxypropiophenone (1) followed by conversion of the phenol to its methyl by means of MeI provides the intermediate 2; the nitro group is then reduced to the corresponding amine (3) by catalytic reduction. The newly formed amine is then replaced by a nitrile group by successive conversion to the diazonium salt by means of nitrous acid followed by treatment with cuprous cyanide (4). Rxn with aluminium chloride|AlCl₃]] cleaves the methyl ether to afford the ortho acylphenol (5). This is converted to the chromone/flavone (6) in a Kostanecki acylation rxn with BzCl and NaOBz. The nitrile is next hydrolyzed to the carboxylic acid (7) by means of SOCl₂ and that treated with β-Piperidylethanol. There is thus obtained flavoxate (8), a muscle relaxant whose name reflects its flavone nucleus.

Notes

^ Zakir SM, Zaka-ur-Rab S, Salman MT, Khan RA. Bilateral acute angle closure glaucoma in a 50 year old female after oral administration of flavoxate. British Journal of Clinical Pharmacology. 2008. 66(5):726-727
^ Re, P. D.; Verlicchi, L.; Setnikar, I. (1960). "Some Basic Derivatives of 3-Methylflavone-8-carboxylic Acid". Journal of Medicinal and Pharmaceutical Chemistry 2 (3): 263. doi:10.1021/jm50010a002. edit

References

Brenner, G. M. (2000). Pharmacology. Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6
Canadian Pharmacists Association (2000). Compendium of Pharmaceuticals and Specialties (25th ed.). Toronto, ON: Webcom. ISBN 0-919115-76-4
U.S. National Library of Medicine, National Institutes of Health. "Flavoxate". PubMed Health. http://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0000753

UpToDate Contents

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1. 女性における尿失禁の治療および予防 treatment and prevention of urinary incontinence in women

English Journal

Persistence with prescribed antimuscarinic therapy for overactive bladder: a UK experience.

Wagg A, Compion G, Fahey A, Siddiqui E.SourceUniversity of Alberta, Edmonton, AB, Canada Astellas Pharma Europe Astellas Pharma UK, Staines, UK.
BJU international.BJU Int.2012 Dec;110(11):1767-74. doi: 10.1111/j.1464-410X.2012.11023.x. Epub 2012 Mar 12.
Study Type--Therapy (prevalence) Level of Evidence 2b. What's known on the subject and What does the study add Persistence with long-term medication in chronic diseases is typically low and that for overactive bladder medication is lower than average. Sub-optimal persistence is a major challenge f
PMID 22409769

Possible involvement of calcium channels and plasma membrane receptors on Staurosporine-induced neurite outgrowth.

Zhaleh H, Azadbakht M, Bidmeshki Pour A.SourceDepartment of Biology, Razi University, Taqe Bostan, Baghe Abrisham, Kermanshah, Iran. hossain_jale@yahoo.com
Bosnian journal of basic medical sciences / Udruženje basičnih mediciniskih znanosti = Association of Basic Medical Sciences.Bosn J Basic Med Sci.2012 Feb;12(1):20-5.
Staurosporine as a protein kinases inhibitor induced cell death or neurite outgrowth in PC12 cells. We investigated the involvement of calcium channel and plasma membrane receptors on staurosporine inducing neurite outgrowth in PC12 cells. PC12 cells were preincubated with NMDA receptor inhibitors (
PMID 22364299

Erythema and hand edema due to flavoxate.

Moreno Escobosa MC, Cruz Granados S, Moya Quesada MC.SourceUnidad de Alergia, Hospital Torrecárdenas, Almería, Spain. moreno.escobosa@terra.es
Journal of investigational allergology & clinical immunology : official organ of the International Association of Asthmology (INTERASMA) and Sociedad Latinoamericana de Alergia e Inmunología.J Investig Allergol Clin Immunol.2012;22(5):390-1.
PMID 23101324

Japanese Journal

夜間頻尿に対する塩酸フラボキサート就寝前投与の効果

嘉手川豪心,菅谷公男,大城吉則 [他],宮里実,安次富勝博,名嘉栄勝,大城琢磨,田崎新資,西島さおり,諸角誠人,大湾知子
西日本泌尿器科 71(12), 637-642, 2009-12-20
NAID 10026433343

夜間頻尿を有するα1アドレナリン受容体遮断薬投与中の前立腺肥大症患者に対する塩酸フラボキサートの有効性の検討

加藤忍,日下守,白木良一 [他],泉谷正伸,浅野晴好,大木隆弘,柳岡正範,星長清隆
泌尿器科紀要 54(3), 173-177, 2008-03
塩酸タムスロシンあるいはナフトピジルを1ヵ月以上投与しても夜間排尿回数が2回以上の前立腺肥大症患者52例(平均年齢72.1歳)を対象として, 塩酸フラボキサート400～600mg/日を8～12週投与し, その有用性と安全性を検討した。塩酸フラボキサート投与前後で夜間排尿回数は3.8回→2.7回へ有意に減少し, 国際前立腺症状スコア, QOLスコア, 前立腺肥大症影響度ス …
NAID 120001178020

MP-021 温度上昇によってもたらされるヒト膀胱平滑筋電位依存性L型Ca^<2+>電流に対するFlavoxateの温度依存性効果の検討(一般演題ポスター,第94回日本泌尿器科学会総会)

友田稔久,寺本憲功,関成人,伊東祐之,内藤誠二
日本泌尿器科學會雜誌 97(2), 372, 2006-03-10
NAID 110005855278

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リンク元	「フラボキサート」「フラボキセート」
拡張検索	「flavoxate hydrochloride」

「フラボキサート」

Flavoxate
Systematic (IUPAC) name
	2-(1-piperidyl)ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682706
Identifiers
CAS Registry Number	15301-69-6
ATC code	G04BD02
PubChem	CID: 3354
DrugBank	DB01148
ChemSpider	3237
UNII	3E74Y80MEY
KEGG	D07961
ChEBI	CHEBI:5088
ChEMBL	CHEMBL1493
Chemical data
Formula	C24H25NO4
Molecular mass	391.46 g/mol
	SMILES O=C(OCCN1CCCCC1)c4cccc2c4O/C(=C(\C2=O)C)c3ccccc3;
	InChI InChI=1S/C24H25NO4/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25/h2,4-5,8-12H,3,6-7,13-16H2,1H3 ; Key:SPIUTQOUKAMGCX-UHFFFAOYSA-N ;
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英: flavoxate
同: フラボキセート
化: フラボキサート塩酸塩塩酸フラボキサート flavoxate hydrochloride
商: アポラキート、ウロステート、サワダロン、ジステリンク、ハルニン、フラボサート、フラボネート、ブラダロン、フレキシン、プログット、ボラボラン、ユリナロン、ラトボレール、ルアダン、ロラーム
関: その他の泌尿生殖器官及び肛門用薬

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「フラボキセート」

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英: flavoxate
関: フラボキサート

「flavoxate hydrochloride」

　　[★] フラボキサート。塩酸フラボキサート

[1] Zakir SM, Zaka-ur-Rab S, Salman MT, Khan RA. Bilateral acute angle closure glaucoma in a 50 year old female after oral administration of flavoxate. British Journal of Clinical Pharmacology. 2008. 66(5):726-727

[2] Re, P. D.; Verlicchi, L.; Setnikar, I. (1960). "Some Basic Derivatives of 3-Methylflavone-8-carboxylic Acid". Journal of Medicinal and Pharmaceutical Chemistry 2 (3): 263. doi:10.1021/jm50010a002. edit

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flavoxate