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Piroxicam is a nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful inflammatory conditions like arthritis.^[2]^[3] Piroxicam works by preventing the production of endogenous prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling.^[2] The medicine is available as capsules, tablets and (not in all countries) as a prescription-free gel 0.5%.^[4] It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract.^[2] Piroxicam is one of the few NSAIDs that can be given parenteral routes.

It was patented in 1968 by Pfizer and approved for medical use in 1979.^[5] It became generic in 1992,^[6] and is marketed worldwide under many brandnames.^[1]

Medical uses

It is used in the treatment of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and act as an analgesic, especially where there is an inflammatory component.^[2] The European Medicines Agency issued a review of its use in 2007 and recommended that its use be limited to the treatment of chronic inflammatory conditions, as it is only in these circumstances that its risk-benefit ratio proves to be favourable.^[4]^[7]

Adverse effects

As with other NSAIDs the principal side effects include: digestive complaints like nausea, discomfort, diarrhoea and bleeds or ulceration of the stomach, as well as headache, dizziness, nervousness, depression, drowsiness, insomnia, vertigo, hearing disturbances (such as tinnitus), high blood pressure, oedema, light sensitivity, skin reactions (including, albeit rarely, Stevens–Johnson syndrome and toxic epidermal necrolysis) and rarely, kidney failure, pancreatitis, liver damage, visual disturbances, pulmonary eosinophilia and alveolitis.^[4] Compared to other NSAIDs it is more prone to causing gastrointestinal disturbances and serious skin reactions.^[4]

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.^[8]^[9] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.^[8]^[9]

Mechanism of action

Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic and antipyretic properties.^[4]

Chemical properties

Piroxicam exists as alkenol tautomer in organic solvents and as zwitterionic form in water.^[10]

History

The project that produced piroxicam began in 1962 at Pfizer; the first clinical trial results were reported in 1977, and the product launched in 1980 under the brand name "Feldene".^[6]^[11] Major patents expired in 1992^[6] and the drug is marketed worldwide under many brandnames.^[1]

References

^ ^a ^b ^c Drugs.com Drugs.com international listings for piroxicam Page accessed July 3, 2015
^ ^a ^b ^c ^d ^e ^f ^g Brayfield, A, ed. (14 January 2014). "Piroxicam". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 24 June 2014.
^ "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999: 97. Cite journal requires |journal= (help)
^ ^a ^b ^c ^d ^e Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. pp. 665, 673–674. ISBN 978-0-85711-084-8.
^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 519. ISBN 9783527607495.
^ ^a ^b ^c Lombardino, JG; Lowe, JA 3rd (2004). "The role of the medicinal chemist in drug discovery--then and now". Nat Rev Drug Discov. 3 (10): 853–62. doi:10.1038/nrd1523. PMID 15459676. S2CID 11225541.. See: [1] Box 1: Discovery of piroxicam (1962–1980)
^ "COMMITTEE FOR MEDICINAL PRODUCTS FOR HUMAN USE (CHMP) OPINION FOLLOWING AN ARTICLE 31(2) REFERRAL PIROXICAM CONTAINING MEDICINAL PRODUCTS" (PDF). European Medicines Agency. London, UK: European Medicines Agency. 20 September 2007. Retrieved 24 June 2014.
^ ^a ^b "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.
^ ^a ^b "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.
^ Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L (2015). "Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study". RSC Advances. 5 (40): 31852–31860. doi:10.1039/c5ra03653d.
^ 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. PMID 342691.

UpToDate Contents

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1. 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 [show details]
…ulceration as well. In one study of 373 cases of TEN or SJS and 1720 controls, the oxicam NSAIDs (piroxicam and tenoxicam) had the highest risk (relative risk of 34), while the relative risks were less with …
2. 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 [show details]
…either osteoarthritis (OA) or rheumatoid arthritis (RA) to two NSAIDs from two different classes: piroxicam (an oxicam) and ketoprofen (a phenylpropionic acid derivative) . Patients were initially treated…
3. 非ステロイド性抗炎症薬（NSAID）：心血管系への有害作用nsaids adverse cardiovascular effects [show details]
…ketoprofen, flurbiprofen, oxaprozin, etodolac, tolmetin, sulindac, indomethacin, ketorolac, meloxicam, piroxicam, meclofenamate, mefenamic acid, and nabumetone. The cyclooxygenase (COX)-2 selective NSAIDs (coxibs)…
4. 妊娠中や授乳中に使用するリウマチ性疾患の治療薬の安全性safety of rheumatic disease medication use during pregnancy and lactation [show details]
…population-based studies, these observations applied to exposures to ibuprofen, naproxen, diclofenac, and piroxicam, except for a borderline association of ibuprofen use during the first trimester with structural…
5. 発作性片側頭痛：治療および予後paroxysmal hemicrania treatment and prognosis [show details]
…mainly in isolated cases, include aspirin , ibuprofen , naproxen , diclofenac , ketoprofen , and piroxicam beta-cyclodextrin . Limited success in the treatment of paroxysmal hemicrania has been reported…

English Journal

Aspartame as a co-former in co-amorphous systems.

Wu W1, Löbmann K1, Schnitzkewitz J1, Knuhtsen A2, Pedersen DS2, Grohganz H3, Rades T1.
International journal of pharmaceutics.Int J Pharm.2018 Oct 5;549(1-2):380-387. doi: 10.1016/j.ijpharm.2018.07.063. Epub 2018 Jul 31.
PMID 30075253

Ephedra gerardiana aqueous ethanolic extract and fractions attenuate Freund Complete Adjuvant induced arthritis in Sprague Dawley rats by downregulating PGE2, COX2, IL-1β, IL-6, TNF-α, NF-kB and upregulating IL-4 and IL-10.

Uttra AM1, Alamgeer2, Shahzad M3, Shabbir A4, Jahan S5.
Journal of ethnopharmacology.J Ethnopharmacol.2018 Oct 5;224:482-496. doi: 10.1016/j.jep.2018.06.018. Epub 2018 Jun 18.
PMID 29920358

Design, synthesis of novel isoindoline hybrids as COX-2 inhibitors: Anti-inflammatory, analgesic activities and docking study.

Labib MB1, Sharkawi SMZ2, El-Daly M3.
Bioorganic chemistry.Bioorg Chem.2018 Oct;80:70-80. doi: 10.1016/j.bioorg.2018.05.018. Epub 2018 May 21.
PMID 30005203

Japanese Journal

がく関節痛に対する消炎鎮痛剤Ｐｉｒｏｘｉｃａｍ（Ｆｅｌｄｅｎｅ）の臨床使用成績

小島真一,古田哲,田中耕一郎,榊原一彦,金平正三,山田史郎,高井克憙,深谷昌彦,鬼塚啓史,樋田謙二郎,喜久田利弘,福田仁一,山田長敬,滝川幹男,冨田陽二,小谷英二,橋本幸典,大谷端夫,加納彰,倉内淳,鬼塚謙治
日本口腔外科学会雑誌 30(1), 81-87, 1984
… Clinical study on Piroxicam (Feldene), anti-inflamatory analgesic, for temporomandibular joint pain.<BR>Clinical studies on Piroxicam (Feldene) for the treatment of temporomandibular joint pain were carried out. …
NAID 130001358514

Related Pictures

Feldene - Piroxicam: Pain Relief Uses, Side Effects & Where To Buy Santis.be - Feldene Gel Tube 50 Gr 0.5 % Feldene Gel - Alpha First Aid Feldene - Фелдене PFIZER - FELDENE PIROXICAM 20 MG CAJA X 10 CÁPSULAS FELDENE 20MG - Online Medical Store in Pakistan PFIZER - FELDENE 20 MG CAJA CON 40 CÁPSULAS - ANTIINFLAMATORIO FELDENE - Unipharma Pharmaceutical Industries

★リンクテーブル★

リンク元

「ピロキシカム」

Piroxicam
Clinical data
Pronunciation	/paɪˈrɒksɪˌkæm/
Trade names	Feldene, others
Other names	Piroksikam, piroxikam
AHFS/Drugs.com	Monograph
MedlinePlus	a684045
Pregnancy; category	AU: C; D (US), if used during the 3rd trimester, as it may cause ductus arteriosus.;
Routes of; administration	By mouth
ATC code	M01AC01 (WHO) M02AA07 (WHO), S01BC06 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) ; CA: ℞-only ; UK: POM (Prescription only) ; US: ℞-only ;
Pharmacokinetic data
Protein binding	99%
Metabolism	Liver-mediated hydroxylation and glucuronidation
Elimination half-life	50 hours
Excretion	Urine, faeces
Identifiers
	IUPAC name 4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide;
CAS Number	36322-90-4 ;
PubChem CID	54676228;
IUPHAR/BPS	7273;
DrugBank	DB00554 ;
ChemSpider	10442653 ;
UNII	13T4O6VMAM;
KEGG	D00127 ;
ChEBI	CHEBI:8249 ;
ChEMBL	ChEMBL527 ;
CompTox Dashboard (EPA)	DTXSID5021170 ;
ECHA InfoCard	100.048.144
Chemical and physical data
Formula	C15H13N3O4S
Molar mass	331.35 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(verify)

　　[★]

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

[drugsInternat-1] Drugs.com Drugs.com international listings for piroxicam Page accessed July 3, 2015

[MD-2] ^ ^a ^b ^c ^d ^e ^f ^g Brayfield, A, ed. (14 January 2014). "Piroxicam". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 24 June 2014.

[3] "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999: 97. Cite journal requires |journal= (help)

[BNF-4] Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. pp. 665, 673–674. ISBN 978-0-85711-084-8.

[Fis2006-5] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 519. ISBN 9783527607495.

[NRDD-6] Lombardino, JG; Lowe, JA 3rd (2004). "The role of the medicinal chemist in drug discovery--then and now". Nat Rev Drug Discov. 3 (10): 853–62. doi:10.1038/nrd1523. PMID 15459676. S2CID 11225541.. See: [1] Box 1: Discovery of piroxicam (1962–1980)

[EMA-7] "COMMITTEE FOR MEDICINAL PRODUCTS FOR HUMAN USE (CHMP) OPINION FOLLOWING AN ARTICLE 31(2) REFERRAL PIROXICAM CONTAINING MEDICINAL PRODUCTS" (PDF). European Medicines Agency. London, UK: European Medicines Agency. 20 September 2007. Retrieved 24 June 2014.

[FDA_PR_20201015-8] "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.

[FDA_safety_20201015-9] "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.

[10] Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L (2015). "Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study". RSC Advances. 5 (40): 31852–31860. doi:10.1039/c5ra03653d.

[11] 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. PMID 342691.

v t e Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
Pyrazolones / Pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
Salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
Acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
Oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
N-Arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin
Coxibs	Apricoxib Celecoxib Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
Other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase/Orgotein Tenidap
Combinations	Ibuprofen/paracetamol Meloxicam/bupivacaine
Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.

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案内

Feldene