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a nonsteroidal anti-inflammatory drug (trade name Feldene) used to treat arthritis and other inflammatory conditions (同)Feldene

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/17 11:15:29」(JST)

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Piroxicam (in some countries spelled "Piroksikam") is a non-steroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and act as an analgesic, especially where there is an inflammatory component. Piroxicam works by preventing the establishment of a certain type of body chemicals which contributes to inflammation, pain, stiffness, tenderness and swelling. The medicine is available as capsules, tablets and (not in all countries) as a prescription-free gel 0,5%.^[1] It is manufactured by Pfizer under the tradename Feldene, and is available in Canada, the UK, Spain, Portugal, Belgium, Australia, Italy, Brazil, Indonesia, Pakistan and the United States, and under the tradename Brexidol in the Scandinavian countries. It is also manufactured by Bosnalijek under the tradename Roxam, and is available in Eastern Europe including Russia, Africa, and the Middle East. In India, it is available by the tradename Dolonex. In Thailand it is available by the tradename Fasden. It is manufactured as a patch in Korea for use in China under the trade name Trast..

The first study of theraputic use in humans was reported in 1977 ^[2]

It is also used in veterinary medicine to treat certain neoplasias expressing cyclooxygenase (COX) receptors, such as bladder, colon, and prostate cancers.

Mechanism of action

Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic and antipyretic properties. It undergoes enterohepatic circulation.

Adverse effects

Piroxicam use can result in gastrointestinal toxicity, tinnitus, dizziness, headache, rash, and pruritus. The most severe adverse reactions are peptic ulceration, gastrointestinal bleeding, and severe skin reactions including Stevens–Johnson syndrome and toxic epidermal necrolysis. Approximately 30% of all patients receiving daily doses of 20 mg of piroxicam experience side effects.^[3]

In rare cases, piroxicam may cause skin to become more sensitive to sunlight.^[4]

Synthesis

The reaction of saccharin with sodium hydroxide results in substitution of the imide hydrogen atom of saccharin with sodium, giving a sodium salt. The resulting product is reacted with methyl chloroacetate, giving the saccharin-substituted acetic acid methyl ester. Upon reaction with sodium methoxide in dimethylsulfoxide, the product undergoes rearrangement into 1,1-dioxide 3-methoxycarbonyl-3,4-dihydro-2-H-1,2-benzothiazin-4- one.

This product is methylated at the nitrogen atom using methyl iodide, giving. Finally, reaction of the resulting product with 2-aminopyridine gives piroxicam.^[5]^[6]^[7]

Isoxicam

Isoxicam, 1,1-dioxide 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide, is synthesized analogous to piroxicam, using amidation of 1,1-dioxide 3-methoxycarbonyl-3,4-dihydro-2-H-1,2-benzothiazine-4-one in the last stage with 3-amino-5-methylisoxazole, instead of 2-aminopyridine.^[8]

It is used for the same indications as piroxicam. Synonyms for isoxicam are floxicam and maxicam.

References

^ NHS Choices. "Piroxicam (Piroxicam 0.5% gel)". NHS Choices Information, UK. Retrieved 7 May 2014.
^ Weintraub M, Jacox RF, Angevine CD, Atwater EC (1977). "Piroxicam (CP 16171) in rheumatoid arthritis: a controlled clinical trial with novel assessment techniques". Journal of Rheumatology. 4 (4): 393–404.
^ New Zealand Medicines and Medical Devices Safety Authority. "Candyl Medicines datasheet". Retrieved 2006-09-10.
^ Mammen L, Schmidt CP (August 1995). "Photosensitivity reactions: a case report involving NSAIDs". Am Fam Physician 52 (2): 575–9. PMID 7625330.
^ F. Zumstein, E. Assmann, R. Koenigsberger, R. Holzbauer, F. Zunstein, DE 2208351 (1972).
^ M. Schwartz, J. Shovel, U.S. Patent 3,787,324 (1974)
^ Lombardino, J. G.; Wiseman, E. H. (1971). "Antiinflammatory 3,4-dihydro-2-alkyl-3-oxo-2H-1,2-benzothiazine-4-carboxamide 1,1-dioxides". Journal of Medicinal Chemistry 14 (10): 973. doi:10.1021/jm00292a022. PMID 5115698. edit
^ Zinnes, H.; Sircar, J. C.; Lindo, N.; Schwartz, M. L.; Fabian, A. C.; Shavel, J.; Kasulanis, C. F.; Genzer, J. D.; Lutomski, C.; Dipasquale, G. (1982). "Isoxicam and related 4-hydroxy-N-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide, 1,1-dioxides. Potent nonsteroidal antiinflammatory agents". Journal of Medicinal Chemistry 25 (1): 12–8. doi:10.1021/jm00343a003. PMID 7086815. edit

UpToDate Contents

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1. 非ステロイド性抗炎症剤（NSAIDs）：成人における治療使用および効果のばらつき nsaids therapeutic use and variability of response in adults
2. 非選択性非ステロイド性抗炎症剤（NSAIDs）：副作用の概要 nonselective nsaids overview of adverse effects
3. 光線過敏症（光線皮膚症）：臨床症状、診断、および治療 photosensitivity disorders photodermatoses clinical manifestations diagnosis and treatment
4. 発作性片側頭痛：治療および予後 paroxysmal hemicrania treatment and prognosis
5. 成人における複合性局所疼痛症候群の予防およびマネージメント prevention and management of complex regional pain syndrome in adults

English Journal

Ultrasound influence on the solubility of solid dispersions prepared for a poorly soluble drug.

Pereira SV1, Colombo FB2, de Freitas LA3.
Ultrasonics sonochemistry.Ultrason Sonochem.2016 Mar;29:461-9. doi: 10.1016/j.ultsonch.2015.10.022. Epub 2015 Oct 31.
Solid dispersions have been successfully used to enhance the solubility of several poorly water soluble drugs. Solid dispersions are produced by melting hydrophilic carriers and mixing in the poorly water soluble drug. Supersaturation is obtained by quickly cooling the mixture until it solidifies, t
PMID 26548840

Scavenging of photogenerated ROS by Oxicams. Possible biological and environmental implications.

Ferrari GV1, Natera J2, Paulina Montaña M1, Muñoz V1, Gutiérrez EL1, Massad W2, Miskoski S2, García NA3.
Journal of photochemistry and photobiology. B, Biology.J Photochem Photobiol B.2015 Dec;153:233-9. doi: 10.1016/j.jphotobiol.2015.09.024. Epub 2015 Sep 28.
The profusely employed drugs Piroxicam (Piro), Tenoxicam (Teno) and Meloxicam (Melo) belonging to the non-steroidal antiinflammatory drug (NSAID) family of the Oxicams (Oxis) were studied in the frame of two specific conditions: (a) their ROS scavenging ability, in relation to a possible biological
PMID 26453988

Piroxicam, a traditional non-steroidal anti-inflammatory drug (NSAID) causes apoptosis by ROS mediated Akt activation.

Rai N1, Sarkar M2, Raha S3.
Pharmacological reports : PR.Pharmacol Rep.2015 Dec;67(6):1215-23. doi: 10.1016/j.pharep.2015.05.012. Epub 2015 May 30.
BACKGROUND: Piroxicam (Px) belongs to the oxicam group of the non-steroidal anti-inflammatory drugs (NSAIDs) and have been shown to exert chemopreventive and chemotherapeutic effects in animal models and cultured animal cells. However, little is known about the mode of action of Px and its cellular
PMID 26481545

Japanese Journal

Advancement of oral squamous cell carcinoma due to careless tooth extraction: Two canine cases

石川剛司,信田卓男,圓尾拓也,杉山大樹,金久保佳代,伊藤哲郎,茅沼秀樹,菅沼常徳
日本獣医がん学会雑誌 1(3), 52-57, 2010
… Subsequently, both cases received carboplatin and piroxicam treatment. …
NAID 130000438452

Effect of Particle Size on Skin Permeation and Retention of Piroxicam in Aqueous Suspension

Moribe Kunikazu,Shibata Mizuho,Furuishi Takayuki [他],Higashi Kenjirou,Tomono Kazuo,Yamamoto Keiji
Chemical and Pharmaceutical Bulletin 58(8), 1096-1099, 2010
… The effects of particle size on the skin permeation and retention of piroxicam (PXC) in an aqueous suspension were investigated. …
NAID 130000299822

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リンク元

「ピロキシカム」

Piroxicam
Systematic (IUPAC) name
	(8E)-8-[hydroxy-(pyridin-2-ylamino)methylidene]-; 9-methyl-10,10-dioxo-10λ6-thia-9-azabicyclo[4.4.0]; deca-1,3,5-trien-7-one
Clinical data
Trade names	Feldene, "Arantil", "Brexidol", "Brexin", "Erazon", "Exipan", "Faxiden", "Felden", "Feldoral", "Flamexin", "Hawksone", "Hotemin", "Lubor", "Mobilis", "Pirox von ct", "Proponol", "Reumador", "Remox", "Roxam", "Sinartrol", "Toricam", "Tracam", "Ugesic", "Veral" and "Vurdon"
AHFS/Drugs.com	monograph
MedlinePlus	a684045
Pregnancy cat.	C (AU) C (US) D, if used during the 3rd trimester; may cause ductus arteriosus.
Legal status	Prescription Only (S4) (AU) ℞-only (CA) POM (UK) ℞-only (US)
Routes	Oral
Pharmacokinetic data
Protein binding	99.3%
Metabolism	4 to 10% renal
Half-life	50 hours
Excretion	Urine, faeces
Identifiers
CAS number	36322-90-4
ATC code	M01AC01 M02AA07, S01BC06
PubChem	CID 5280452
DrugBank	DB00554
ChemSpider	10442653
UNII	13T4O6VMAM
KEGG	D00127
ChEBI	CHEBI:8249
ChEMBL	CHEMBL527
Chemical data
Formula	C15H13N3O4S
Mol. mass	331.348 g/mol
	SMILES OC=2c1ccccc1S(=O)(=O)N(C)C=2C(=O)Nc3ccccn3;
	InChI InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20) ; Key:QYSPLQLAKJAUJT-UHFFFAOYSA-N ;
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　　[★]

英: piroxicam
ラ: piroxicamum
商: アルデイン、ドラフトン、バキソ、パルパシン、ピオパール、フェルデン、ベリーズ。Feldene
関: 非ステロイド性抗炎症薬、(プロドラッグ)アンピロキシカム

[1] NHS Choices. "Piroxicam (Piroxicam 0.5% gel)". NHS Choices Information, UK. Retrieved 7 May 2014.

[2] Weintraub M, Jacox RF, Angevine CD, Atwater EC (1977). "Piroxicam (CP 16171) in rheumatoid arthritis: a controlled clinical trial with novel assessment techniques". Journal of Rheumatology. 4 (4): 393–404.

[3] New Zealand Medicines and Medical Devices Safety Authority. "Candyl Medicines datasheet". Retrieved 2006-09-10.

[4] Mammen L, Schmidt CP (August 1995). "Photosensitivity reactions: a case report involving NSAIDs". Am Fam Physician 52 (2): 575–9. PMID 7625330.

[5] F. Zumstein, E. Assmann, R. Koenigsberger, R. Holzbauer, F. Zunstein, DE 2208351 (1972).

[6] M. Schwartz, J. Shovel, U.S. Patent 3,787,324 (1974)

[7] Lombardino, J. G.; Wiseman, E. H. (1971). "Antiinflammatory 3,4-dihydro-2-alkyl-3-oxo-2H-1,2-benzothiazine-4-carboxamide 1,1-dioxides". Journal of Medicinal Chemistry 14 (10): 973. doi:10.1021/jm00292a022. PMID 5115698. edit

[8] Zinnes, H.; Sircar, J. C.; Lindo, N.; Schwartz, M. L.; Fabian, A. C.; Shavel, J.; Kasulanis, C. F.; Genzer, J. D.; Lutomski, C.; Dipasquale, G. (1982). "Isoxicam and related 4-hydroxy-N-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide, 1,1-dioxides. Potent nonsteroidal antiinflammatory agents". Journal of Medicinal Chemistry 25 (1): 12–8. doi:10.1021/jm00343a003. PMID 7086815. edit

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piroxicam