Tenoxicam: Difference between revisions

{{Short description|Non-steroidal anti-inflammatory drug}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 443408783

| IUPAC_name = (3''E'')-3-[hydroxy(pyridin-2-ylamino)methylene] -2-methyl-2,3-dihydro-4''H''-thieno[2,3-''e''] [1,2]thiazin-4-one 1,1-dioxide

| image = Tenoxicam FormulaV1.svg

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|international|tenoxicam}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = S4

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = POM

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration = Oral

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound = High

| metabolism =

| elimination_half-life = 30–140 hours

| excretion =

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 59804-37-4

| ATC_prefix = M01

| ATC_suffix = AC02

| PubChem = 5282194

| DrugBank =

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 32192

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4471584

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z1R9N0A399

<!--Chemical data-->

| C=13 | H=11 | N=3 | O=4 | S=2

| melting_point = 209

| melting_high = 213

| melting_notes = (dec.)

<!-- Definition and medical uses -->

'''Tenoxicam''', sold under the brand name '''Mobiflex''' among others, is a [[nonsteroidal anti-inflammatory drug]] (NSAID). It is used to relieve [[inflammation]], [[Swelling (medical)|swelling]], stiffness, and pain associated with [[rheumatoid arthritis]], [[osteoarthritis]], [[ankylosing spondylitis]] (a type of arthritis involving the [[Vertebral column|spine]]), [[tendinitis]] (inflammation of a tendon), [[bursitis]] (inflammation of a [[Synovial bursa|bursa]], a [[Synovial fluid|fluid]]-filled sac located around joints and near the bones), and [[Enthesopathy|periarthritis]] of the shoulders or hips (inflammation of tissues surrounding these joints).<ref name=NHS/>

<!-- Side effects and mechanisms -->

Tenoxicam belongs to the class of NSAIDs known as [[oxicam]]s.

<!-- Society and culture -->

It was patented in 1974 by [[Hoffmann–La Roche|Roche]] and approved for medical use in 1987.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=519 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA519 |language=en}}</ref> It is available as a [[Prescription drug|prescription-only drug]] in the [[United Kingdom]] and other countries, but not in the [[United States|US]]. Outside the United Kingdom, tenoxicam is also marketed under brand names including Tilatil, Tilcitin, and Alganex.<ref name=NHS>{{cite web | work = NHS | url = http://www.nhs.uk/conditions/arthritis/pages/selectorshow.aspx?medicine=Tenoxicam | title = Medicines A-Z - Tenoxicam | access-date = July 3, 2015 }}</ref><ref>{{cite web | work = Drugs.com | url = https://www.drugs.com/international/tenoxicam.html | title = Drugs.com international listings for Tenoxicam | access-date = July 3, 2015 }}</ref>

The drug is contraindicated for patients who are seniors who have been given [[anesthesia]] or [[surgery]]; are at risk of increased bleeding or kidney failure; have an active inflammatory disease involving the stomach or intestine (like [[ulcerative colitis]]); have an active stomach or [[intestinal ulcer]]; have had an acute asthmatic attack, hives, rhinitis (inflammation of the inner lining of the nasal passage), or other allergic reactions caused by [[aspirin]] or other nonsteroidal anti-inflammatory drugs (for example [[diclofenac]], [[ibuprofen]], [[indomethacin]], [[naproxen]]).<ref>NHS [http://medguides.medicines.org.uk/nhs/medicine.aspx?name=Tenoxicam&use=Soft%20tissue%20injury&preparation=2&section=suitability Patient warnings] Page accessed July 3, 2015</ref><ref name=":3">{{Cite web|title = Mobiflex Tablets 20mg - Summary of Product Characteristics (SPC) - (eMC)|url = https://www.medicines.org.uk/emc/medicine/22684#ORIGINAL|website = www.medicines.org.uk|access-date = 2015-12-07}}</ref>

Common side effects that have been observed with tenoxicam include peptic ulceration, dyspepsia, nausea, constipation, abdominal pain, diarrhea, rash, headache, edema, renal failure, and vertigo.<ref name=":2" /><ref name=":3" /><ref name=":4">Tilcotil. (2010). ''New Zealand Consumer Medicine Information''. http://www.medsafe.govt.nz/consumers/cmi/t/tilcotil.pdf</ref> In rare cases, tenoxicam and other NSAIDs can contribute to thrombotic events, Stevens-Johnson Syndrome, and toxic epidermal necrolysis.<ref>{{cite journal | vauthors = Mockenhaupt M, Viboud C, Dunant A, Naldi L, Halevy S, Bouwes Bavinck JN, Sidoroff A, Schneck J, Roujeau JC, Flahault A | display-authors = 6 | title = Stevens-Johnson syndrome and toxic epidermal necrolysis: assessment of medication risks with emphasis on recently marketed drugs. The EuroSCAR-study | journal = The Journal of Investigative Dermatology | volume = 128 | issue = 1 | pages = 35–44 | date = January 2008 | pmid = 17805350 | doi = 10.1038/sj.jid.5701033 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Harr T, French LE | title = Toxic epidermal necrolysis and Stevens-Johnson syndrome | journal = Orphanet Journal of Rare Diseases | volume = 5 | issue = 1 | pages = 39 | date = December 2010 | pmid = 21162721 | pmc = 3018455 | doi = 10.1186/1750-1172-5-39 | doi-access = free }}</ref><ref>{{cite web | title = Assessment report for Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) and cardiovascular risk. | date = 18 October 2012 | publisher = European Medicines Agency | url = http://www.ema.europa.eu/docs/en_GB/document_library/Report/2012/11/WC500134717.pdf }}</ref>

===Pregnancy and breastfeeding===

It is not recommended that women who are trying to conceive, who are pregnant, or who are breastfeeding take tenoxicam. Tenoxicam can be taken in the first and second trimester when necessary, but it is a contraindication in the third trimester. Some studies have looked at whether or not NSAIDs are able to enter the breast milk and the first few studies have found evidence that NSAIDs can be found in breast milk. Therefore, it is not recommended that women take tenoxicam while breastfeeding.<ref name=":2" /><ref name=":3" /><ref name=":4" />

== Interactions ==

Taking tenoxicam with other drugs can increase the chance of side effects or alter the therapeutic effect of tenoxicam or the other drug, depending on the combination. Drug types the tenoxicam may interact with include: other analgesic NSAIDs, [[Salicylic acid|salicylates]] such as aspirin, [[antacid]]s, anticoagulants, [[cardiac glycoside]]s, [[ciclosporin]], [[quinolone antibiotic]]s, [[Lithium (medication)|lithium therapy]], diuretics and anti-hypertensives, [[methotrexate]], oral anti-diabetics, [[Cholestyramine|colestyramine]], [[dextromethorphan]], [[mifepristone]], corticosteroids, anti-platelet agents and [[selective serotonin reuptake inhibitor]]s (SSRIs), [[tacrolimus]], [[zidovudine]], and gold/[[penicillamine]].<ref name=":2" /><ref name=":3" /><ref name=":4" />

==Mechanism of action==

Like all NSAIDs, the exact mechanism of action of tenoxicam is unknown.{{Dubious|date=July 2017}} Involved in the mechanism of action is inhibition of [[cyclooxygenase]] (COX-1 and COX-2) which leads to the potential adverse effect of increased bleeding.<ref name=":2">{{Cite web|title = Incepta Pharmaceuticals {{!}} Product details|url = http://www.inceptapharma.com/view-product.php?pid=540|website = www.inceptapharma.com|access-date = 2015-12-07}}</ref>

==Society and culture==

Tenoxicam is sold in the form of 20&nbsp;mg tablets with the price of treatment ranging from US$1.29–2.73 per tablet.<ref name=":0">{{Cite web|title = Tenoxicam 20 mg Price Comparisons - Online Pharmacies and Discount Coupons|url = http://www.pharmacychecker.com/generic/price-comparison/tenoxicam/20+mg/|website = www.pharmacychecker.com|access-date = 2015-12-07}}</ref> Recommended dosing calls for tenoxicam to be taken once daily with food. One week is the typical length for treatment, but the treatment length may be extended.<ref name=":2" />

In 2008, the reported sales level for Tilcotil (tenoxicam) was 70 million SEK (approximately US$10.5 million).<ref name=":0" /><ref>{{Cite web|title = Exchange Rate Average (Swedish Krona, US Dollar) - X-Rates|url = http://www.x-rates.com/average/?from=SEK&to=USD&amount=1&year=2008|website = www.x-rates.com|access-date = 2015-12-07}}</ref>

==Research==

The first members of the oxicam family of NSAIDs were brought to market in France in 1982.<ref>{{cite journal | vauthors = Penso D, Roujeau JC, Guillaume JC, Revuz J, Touraine R | title = Toxic epidermal necrolysis after oxicam use | journal = Journal of the American Academy of Dermatology | volume = 14 | issue = 2 Pt 1 | pages = 275–276 | date = February 1986 | pmid = 3485122 | doi = 10.1016/s0190-9622(86)80342-5 }}</ref> Shortly thereafter, tenoxicam went to phase III clinical trials for approval as use as an analgesic began in the 1980s. The general consensus from clinical studies is that tenoxicam has about equal analgesic effect as other NSAIDs and does not elicit any important side effects. More recent clinical trials for tenoxicam are examining the use of tenoxicam independently and in combination with other drugs for more specialized analgesic purposes in surgical operations such as third molar extraction and labor pains.<ref>{{Cite web|title = Search of: tenoxicam - List Results - ClinicalTrials.gov|url = https://www.clinicaltrials.gov/ct2/results?term=tenoxicam&Search=Search|website = www.clinicaltrials.gov|access-date = 2015-12-07}}</ref><ref>{{cite journal | vauthors = Ilhan O, Agacayak KS, Gulsun B, Koparal M, Gunes N | title = A comparison of the effects of methylprednisolone and tenoxicam on pain, edema, and trismus after impacted lower third molar extraction | journal = Medical Science Monitor | volume = 20 | pages = 147–152 | date = January 2014 | pmid = 24473372 | pmc = 3915002 | doi = 10.12659/MSM.890239 }}</ref><ref>{{cite journal | vauthors = Mathias Filho AP, Sidi A | title = Long-term study with Ro 12-0068 (tenoxicam) in the treatment of rheumatoid arthritis | journal = European Journal of Rheumatology and Inflammation | volume = 8 | issue = 1 | pages = 3–8 | date = 1985 | pmid = 3915886 }}</ref>

== See also ==

* [[Piroxicam]]

* [[Meloxicam]]

== References ==

{{Reflist}}

{{Anti-inflammatory and antirheumatic products}}

{{Prostanoid signaling modulators}}

[[Category:Dermatoxins]]

[[Category:Nonsteroidal anti-inflammatory drugs]]

[[Category:Thienothiazines]]

[[Category:2-Pyridyl compounds]]

[[Category:Carboxamides]]

[[Category:Sultams]]