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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/07/30 10:48:31」(JST)
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Floctafenine
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Systematic (IUPAC) name |
2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)-4-quinolinyl]amino}benzoate
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Clinical data |
AHFS/Drugs.com |
International Drug Names |
Identifiers |
CAS Number |
23779-99-9 |
ATC code |
N02BG04 (WHO) |
PubChem |
CID 3360 |
DrugBank |
DB08976 N |
ChemSpider |
3243 |
Chemical data |
Formula |
C20H17F3N2O4 |
Molar mass |
406.355 g/mol |
SMILES
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FC(F)(F)c1cccc2c(ccnc12)Nc3ccccc3C(=O)OCC(O)CO
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InChI
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InChI=1S/C20H17F3N2O4/c21-20(22,23)15-6-3-5-13-17(8-9-24-18(13)15)25-16-7-2-1-4-14(16)19(28)29-11-12(27)10-26/h1-9,12,26-27H,10-11H2,(H,24,25)
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Key:APQPGQGAWABJLN-UHFFFAOYSA-N
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Floctafenine is a non-steroidal anti-inflammatory drug (NSAID).
Synthesis
Flocatfenine synthesis:
DE 1815467 ; eidem,
U.S. Patent 3,644,368 Roussel Uclaf;
[1]
The scheme involves first the conversion of ortho-trifluoromethyl aniline (1) to a quinolol. The compound is thus condensed with EMME (Ethoxy Methylene Malonic Diethyl Ester) and cyclized thermally (2). That intermediate is then saponified; the resulting acid is decarboxylated and finally converted to the 4-chloroquinoline (3) by reaction with phosphorus oxychloride. The displacement of chlorine with methyl anthranilate (4) then affords the coupled intermediate (5). An ester interchange of that product with glycerol leads to the glyceryl ester. There is thus obtained the NSAID floctafenine.
See also
- Glafenine, a chemically related NSAID
References
- ^ Mouzin, G.; Cousse, H.; Autin, J. M. (1980). "A New, Convenient Synthesis of Glafenine and Floctafenine". Synthesis 1980: 54. doi:10.1055/s-1980-28923.
Prostanoid signaling
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Receptor
(ligands) |
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Enzyme
(inhibitors) |
COX (PTGS) |
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PGD2 synthase |
- Retinoids
- Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
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PGE synthase |
HQL-79
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PGF synthase |
Bimatoprost
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PGI2 synthase |
Tranylcypromine
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TXA synthase |
- Camonagrel
- Dazmegrel
- Dazoxiben
- Furegrelate
- Isbogrel
- Midazogrel
- Nafagrel
- Nicogrelate
- Ozagrel
- Picotamide
- Pirmagrel
- Ridogrel
- Rolafagrel
- Samixogrel
- Terbogrel
- U63557A
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Others |
- Precursors: Linoleic acid
- γ-Linolenic acid (gamolenic acid)
- Dihomo-γ-linolenic acid
- Diacylglycerol
- Arachidonic acid
- Prostaglandin G2
- Prostaglandin H2
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See also: Leukotrienergics
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English Journal
- Simultaneous determination of floctafenine and its hydrolytic degradation product floctafenic acid using micellar liquid chromatography with applications to tablets and human plasma.
- Walash MI, Belal F, El-Enany N, Eid M, El-Shaheny RN.
- Journal of AOAC International.J AOAC Int.2013 Nov-Dec;96(6):1315-24.
- A stability-indicating micellar liquid chromatography (MLC) method was developed and validated for the assay of floctafenine (FLF) in the presence of its degradation product and main metabolite, floctafenic acid (FLA). The analysis was carried out on a CLC Shim-Pack octyl silane (C8) column (150 x 4
- PMID 24645510
- Clinical pharmacology of cyclooxygenase inhibition and pharmacodynamic interaction with aspirin by floctafenine in Thai healthy subjects.
- Maenthaisong R1, Tacconelli S, Sritara P, Del Boccio P, Di Francesco L, Sacchetta P, Archararit N, Aryurachai K, Patrignani P, Suthisisang C.
- International journal of immunopathology and pharmacology.Int J Immunopathol Pharmacol.2013 Apr-Jun;26(2):403-17.
- Floctafenine, a hydroxyquinoline derivative with analgesic properties, is widely used in Thailand and many other countries. The objectives of this study were to evaluate in Thai healthy volunteers: i) the inhibition of whole blood cyclooxygenase(COX)-2 and COX-1 activity by floctafenine and its meta
- PMID 23755755
- Simultaneous HPLC determination of thiocolchicoside and glafenine as well as thiocolchicoside and floctafenine in their combined dosage forms.
- Walash M1, Belal F, Eid M, el-Abass SA.
- Journal of chromatographic science.J Chromatogr Sci.2011 Feb;49(2):159-64.
- Sensitive and accurate high-performance liquid chromatographic methods have been developed for the simultaneous determination of thiocolchicoside (TC)-glafenine (GF) (Mix I) and thiocolchicoside-floctafenine (FN) (Mix II) in their pharmaceutical formulations. The analysis for both mixtures was perfo
- PMID 21223643
Japanese Journal
- 酸性非ステロイド系抗炎症薬物による好中球活性酸素生成の変動
- 岩田 真,佐伯 清美,小渕 浩嗣,渡部 嘉哉,水上 佳与子,吉岡 保,小林 純郎,友田 三保,内海 耕慥
- 炎症 13(2), 125-131, 1993
- … Effect of acidic non-steroidal anti-inflammatory drugs (NSAIDs), indomethacin, floctafenine and tiaprofenic acid, on active oxygen generation from guinea pig peritoneal (GPtPMN) and human peripheral neutrophils (HPPMN) were studied. …
- NAID 130003709406
- Analgesic Action of Amfenac Na, a Non-steroidal Anti-inflammatory Agent
- HIRANUMA Toyokazu,KATO Satoko,HACHISU Mitsugu
- Journal of Pharmacobio-Dynamics 11(9), 612-619, 1988-09
- … floctafenine > …
- NAID 110003636911
- 歯科口腔外科領域における Floctafenine (Idalon^( !R)錠) の臨床的検討
Related Links
- Floctafenine belongs to the class of medications known as nonsteroidal anti-inflammatory drugs (NSAIDs). It is used for the short-term treatment of mild to moderate pain. It acts by blocking the production of chemicals that are ...
- See related floctafenine information Abbreviation Index Indications Pain relief. Dosage Adult: PO Up to 1.2 g/day in divided doses. Click to view floctafenine Dosage by Indications Contraindications Porphyria, hypersensitivity, peptic ...
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