チアプロフェン酸
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/09/05 16:05:10」(JST)
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Tiaprofenic acid
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Systematic (IUPAC) name |
(RS)-2-(5-benzoyl-2-thienyl)propanoic acid
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Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy
category |
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Routes of
administration |
oral |
Legal status |
Legal status |
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Pharmacokinetic data |
Bioavailability |
90% |
Metabolism |
10% hepatic |
Biological half-life |
1.5-2.5h |
Excretion |
50-80% urine |
Identifiers |
CAS Number |
33005-95-7 Y |
ATC code |
M01AE11 (WHO) |
PubChem |
CID 5468 |
DrugBank |
DB01600 Y |
ChemSpider |
5269 Y |
UNII |
1LS1T6R34C Y |
KEGG |
D01325 Y |
ChEBI |
CHEBI:32221 Y |
ChEMBL |
CHEMBL365795 Y |
Synonyms |
5-Benzoyl-α-methyl-2-thiopheneacetic acid |
Chemical data |
Formula |
C14H12O3S |
Molar mass |
260.309 |
Chirality |
Racemic mixture |
SMILES
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O=C(c1sc(cc1)C(C(=O)O)C)c2ccccc2
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InChI
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InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17) Y
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Key:GUHPRPJDBZHYCJ-UHFFFAOYSA-N Y
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(verify) |
Tiaprofenic acid is a non-steroidal anti-inflammatory drug (NSAID) of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain. The typical adult dose is 300 mg twice daily. It is not recommended in children.
It is sparingly metabolised in the liver to two inactive metabolites. Most of the drug is eliminated unchanged in the urine. Renal disease impairs excretion, and it should be used with caution in renal disease.
Long-term use of tiaprofenic acid is associated with severe cystitis, roughly 100 times more commonly than other NSAIDs.[1] It is contraindicated in patients with cystitis and urinary tract infections.
The earliest reports of clinical use are from France in 1975 [2]
It is marketed under the trade names Surgam, Surgamyl and Tiaprofen, and in generic formulations. A sustained-release preparation is available. It is isomer with Suprofen.
References
- ^ Crawford MLA, Waller PC, Wood SM (1997). "Severe cystitis associated with tiaprofenic acid". British Journal of Urology. 79 (4): 578–584. doi:10.1046/j.1464-410X.1997.00094.x. PMID 9126086.
- ^ Pons J, Pasturel A (1975). "[How to improve postoperative complications in stomatological, maxillofacial and plastic surgery: evaluation of tiaprofenic acid]. [French]". Revue d Odonto-Stomatologie. 4 (6): 535–7.
External links
- Manufacturer Data Sheet [1]
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
- High-throughput determination of nonsteroidal anti-inflammatory drugs in human plasma by HILIC-MS/MS.
- Nemoto T1, Lee XP, Kumazawa T, Hasegawa C, Fujishiro M, Marumo A, Shouji Y, Inagaki K, Sato K.Author information 1Department of Legal Medicine, Showa University School of Medicine, Tokyo 142-8555, Japan.AbstractA simple and sensitive method was developed and validated here for the analysis of thirteen nonsteroidal anti-inflammatory drugs (NSAIDs) in human plasma samples by hydrophilic interaction liquid chromatography (HILIC)-tandem mass spectrometry (MS/MS). A small volume of plasma (20μL) spiked with compounds was diluted with 80μL of 10-mM ammonium acetate followed by a simple protein precipitation with 400μL of acetonitrile. After centrifugation, the clear supernatant extract was directly injected into the HILIC-MS/MS, without any solvent evaporation and reconstitution steps. The chromatographic separation of the NSAIDs was achieved on a Unison UK-Amino HILIC column (50mm×3mm i.d., particle size 3μm) with a linear gradient elution system composed of 10mM ammonium acetate (pH 6.8) and acetonitrile at a flow rate of 0.4mL/min. The mass spectra obtained by HILIC-MS showed base peak ions due to [M+H](+) for indomethacin, oxaprozin, ketoprofen, alminoprofen, zaltoprofen, tiaprofenic acid, pranoprofen, and ketoprofen-d3 and due to [M-H](-) for etodolac, ibuprofen, diclofenac, fenoprofen, loxoprofen, naproxen, and ibuprofen-d3. Recoveries of these thirteen NSAIDs in plasma were 34.8-113% and the lower limits of quantitation were 0.125-1.25μg/mL. The intra- and interday coefficient of variations for all drugs in plasma were less than 14.6%. The data obtained from actual plasma determinations of zaltoprofen, ibuprofen, and diclofenac are also presented.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2014 Jan 25;88:71-80. doi: 10.1016/j.jpba.2013.08.023. Epub 2013 Aug 29.
- A simple and sensitive method was developed and validated here for the analysis of thirteen nonsteroidal anti-inflammatory drugs (NSAIDs) in human plasma samples by hydrophilic interaction liquid chromatography (HILIC)-tandem mass spectrometry (MS/MS). A small volume of plasma (20μL) spiked with co
- PMID 24036363
- Time-resolved spectroscopic study of the photochemistry of tiaprofenic acid in a neutral phosphate buffered aqueous solution from femtoseconds to final products.
- Su T1, Ma J, Li MD, Guan X, Yu L, Phillips DL.Author information 1Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, PR China.AbstractThe photo-decarboxylation and overall reaction mechanism of tiaprofenic acid (TPA) was investigated by femtosecond transient absorption (fs-TA), nanosecond transient absorption (ns-TA), and nanosecond time-resolved resonance Raman (ns-TR(3)) spectroscopic experiments in a neutral phosphate buffered solution (PBS). In addition, density functional theory (DFT) calculations were presented to help interpret the experimental results. Resonance Raman and DFT calculation results revealed that the deprotonated tiaprofenic acid (TPA(-)) form was the primary species that is photoexcited in a near neutral PBS aqueous solution. The fs-TA experimental data indicated that the lowest lying excited singlet state S(1) underwent an efficient intersystem crossing process (ISC) to quickly transform into the lowest lying excited triplet state T(1) that then undergoes decarboxylation to generate a triplet biradical species (TB(3)). ns-TA and ns-TR(3) results observed a protonation process for TB(3) to produce a neutral species (TBP(3)) that then decayed via ISC to produce a singlet TBP species that further reacted to make the final product (DTPA). A comparison of the present results for TPA(-) with similar results for the deprotonated form of ketoprofen (KP(-)) in the literature was done to investigate how the thiophene moiety in TPA(-) that replaces one phenyl ring in KP(-) affects the reaction mechanism and photochemistry of these nonsteroidal anti-inflammatory drugs (NSAIDs).
- The journal of physical chemistry. B.J Phys Chem B.2013 Jan 24;117(3):811-24. doi: 10.1021/jp310315f. Epub 2013 Jan 14.
- The photo-decarboxylation and overall reaction mechanism of tiaprofenic acid (TPA) was investigated by femtosecond transient absorption (fs-TA), nanosecond transient absorption (ns-TA), and nanosecond time-resolved resonance Raman (ns-TR(3)) spectroscopic experiments in a neutral phosphate buffered
- PMID 23231046
- Enantioseparations in nonaqueous capillary electrophoresis using charged cyclodextrins.
- Servais AC1, Fillet M.Author information 1Department of Pharmaceutical Sciences, University of Liège, Liège, Belgium. acservais@ulg.ac.beAbstractThe enantioseparation of acidic and basic compounds can be successfully achieved in nonaqueous capillary electrophoresis using single-isomer charged β-cyclodextrin (β-CD) derivatives of opposite charge to that of the analytes. This chapter describes how to separate the enantiomers of three basic substances selected as model compounds, i.e., alprenolol, bupranolol, and terbutaline, using the negatively charged heptakis(2,3-di-O-acetyl-6-O-sulfo)-β-CD. The enantiomers of three acidic drugs (tiaprofenic acid, suprofen, and flurbiprofen) are resolved using a monosubstituted amino β-CD derivative, namely, 6-monodeoxy-6-mono(3-hydroxy)propylamino-β-CD.
- Methods in molecular biology (Clifton, N.J.).Methods Mol Biol.2013;970:297-305. doi: 10.1007/978-1-62703-263-6_19.
- The enantioseparation of acidic and basic compounds can be successfully achieved in nonaqueous capillary electrophoresis using single-isomer charged β-cyclodextrin (β-CD) derivatives of opposite charge to that of the analytes. This chapter describes how to separate the enantiomers of three basic s
- PMID 23283786
Japanese Journal
- Two cases of photocontact dermatitis due to topical ketoprofen : Contrasting clinical appearance by different formulations
- INUI Shigeki,DOI Toshiaki,SHIRAI Hirohiko,ITAMI Satoshi,YOSHIKAWA Kunihiko
- Environmental dermatology : the official journal of the Japanese Society for Contact Dermatitis 10(2), 79-82, 2003-04-01
- NAID 10013246320
- Group study of the optimum concentrations of ketoprofen, tiaprofenic acid, suprofen and oxybenzone for the photopatch testing, and the patch test results of the Japanese Standard Allergens and gold sodium thiosulfate in 2000
- KURIKAWA Yukiko,Research Group of the JSCD
- Environmental dermatology : the official journal of the Japanese Society for Contact Dermatitis 9(2), 39-46, 2002-04-01
- NAID 10013245903
- Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs
- SUGIURA M
- Photodermatol. Photoimmunol. Photomed. 18, 82-89, 2002
- NAID 30005152985
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