Oxaprozin

Last updated
Oxaprozin
Oxaprozin.svg
Clinical data
Trade names Daypro, Dayrun, Duraprox, others
AHFS/Drugs.com Monograph
MedlinePlus a693002
Pregnancy
category
  • C
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 95%
Protein binding 99%
Metabolism Liver—65% oxidation and 35% glucuronic acid conjugation. 5% are active phenolic metabolites.
Elimination half-life 54.9 hours
Identifiers
  • 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.040.254 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H15NO3
Molar mass 293.322 g·mol−1
3D model (JSmol)
  • O=C(O)CCc1nc(c(o1)c2ccccc2)c3ccccc3
  • InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21) Yes check.svgY
  • Key:OFPXSFXSNFPTHF-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Oxaprozin, also known as oxaprozinum, is a nonsteroidal anti-inflammatory drug (NSAID), [1] used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis. Chemically, it is a propionic acid derivative. Safety and efficacy has been established in children over 6 years with juvenile rheumatoid arthritis only, and there is an increased risk of adverse reactions in the elderly population.

Contents

It was patented in 1967 and approved for medical use in 1983. [2]

Medical uses

In 2015, oxaprozin was one of twenty NSAIDs included in a clinical trial to compare the efficacy of NSAIDs in the short-term treatment of ankylosing spondylitis (AS). The NSAIDs were compared by completing randomized controlled trials of NSAIDs in patients with active AS. Efficacy reported at 2–12 weeks and adverse effects were examined. Efficacy was measured by change in pain score and change in the duration of morning stiffness. A total of 26 trials with a total of 3410 participants were completed (58% of the trials had fewer than 50 participants). While all 20 NSAIDs were found to reduce more pain than the placebo, 15 were found to be significantly better. In regards to the decrease of morning stiffness and the likelihood of adverse events, there was no significant difference between NSAIDs. It was concluded that etoricoxib was more effective in reducing pain of AS, however due to small studies and insufficient evidence, no one NSAID could be determined to be the most effective treatment of AS. After etoricoxib, patients taking oxaprozin experienced the least amount of pain with fewer adverse effects than naproxen. [3]

Adverse effects

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. [4] [5] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy. [4] [5]

History

Oxaprozin was developed and patented by Wyeth-Ayerst. [6] The US patent 3578671, Oxazoles, was filed November 6, 1967 and published May 11, 1971. [7] Following the filing of the patent, the first description of oxaprozin exhibiting anti-inflammatory properties was outlined in the article Diaryloxazole and diaylthiazolealkanoci acids: two novel series of non-steroidal anti-inflammatory agents. This article was published in Nature in 1968. [8] [9] In December 1988, Wyeth-Ayerst licensed the marketing rights for the US, Canada, Puerto Rico, and the Caribbean to Searle. [6]

Daypro became available January 5, 1993. Upon its release, “The Pink Sheet” estimated that the average whole sale price of Searle's Daypro was $112.30 for 100 (600 mg) tablets. [6] The price was comparable to other prescription NSAIDs.

Society and culture

FDA approval

The oxaprozin new drug application (NDA 18-841) was submitted to the FDA on August 10, 1982. The drug was granted an “NDA Day” review on June 15–16, 1992. After Searle agreed to complete seven Phase IV postmarketing studies on October 22, the FDA approved Daypro on October 29, 1992. [6]

Since the approval of Daypro by Searle, other companies have submitted abbreviated new drug applications (ANDAs) to the FDA. Daypro by Searle is listed as the Reference Listed Drug to prove the bioequivalence of the ANDAs. Below is a table listing all of the approved oxaprozin products.

Company [10] FDA Approval Date [10]
GD Searle Oct 29, 1992
Apotex IncSep 2, 2004
Dr. Reddy's Labs LTDJan 31, 2001
Ivax Sub TevaMay 13, 2002
Sandoz Jan 31, 2002
Sun Pharm Inds IncJan 3, 2002
Teva Jul 3, 2002

Recalls

Advantage Dose LLC recalled oxaprozin tablets on November 26, 2008. The company was not in conformance with cGMP. (Recall #D-837-2009) [11]

Related Research Articles

Nonsteroidal anti-inflammatory drugs (NSAIDs) are members of a drug class that reduces pain, decreases fever, prevents blood clots, and in higher doses, decreases inflammation. Side effects depend on the specific drug but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

Ibuprofen Medication used for treating pain, fever, and inflammation

Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used by mouth or intravenously. It typically begins working within an hour.

Infliximab

Infliximab, a chimeric monoclonal antibody, sold under the brand name Remicade among others, is a medication used to treat a number of autoimmune diseases. This includes Crohn's disease, ulcerative colitis, rheumatoid arthritis, ankylosing spondylitis, psoriasis, psoriatic arthritis, and Behçet's disease. It is given by slow injection into a vein, typically at six- to eight-week intervals.

Diclofenac Nonsteroidal anti-inflammatory drug

Diclofenac, sold under the brand name Voltaren among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammatory diseases such as gout. It is taken by mouth, rectally in a suppository, used by injection, or applied to the skin. Improvements in pain last for as much as eight hours. It is also available in combination with misoprostol in an effort to decrease stomach problems.

Naproxen A nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout, and fever

Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and last for up to twelve hours.

Rofecoxib nonsteroidal anti-inflammatory drug

Rofecoxib was a COX-2 selective nonsteroidal anti-inflammatory drug (NSAID). It was marketed by Merck & Co. to treat osteoarthritis, rheumatoid arthritis, juvenile rheumatoid arthritis, acute pain conditions, migraine, and dysmenorrhea. Rofecoxib was approved in the US by the US Food and Drug Administration (FDA) in May 1999, and was marketed under the brand names Vioxx, Ceoxx, and Ceeoxx. Rofecoxib was available by prescription in both tablet-form and as an oral suspension.

Celecoxib Nonsteroidal anti-inflammatory drug

Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID). It is used to treat the pain and inflammation in osteoarthritis, acute pain in adults, rheumatoid arthritis, ankylosing spondylitis, painful menstruation, and juvenile rheumatoid arthritis. It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis. It is taken by mouth. Benefits are typically seen within an hour.

Phenylbutazone

Phenylbutazone, often referred to as "bute", is a nonsteroidal anti-inflammatory drug (NSAID) for the short-term treatment of pain and fever in animals.

COX-2 inhibitors are a type of nonsteroidal anti-inflammatory drug (NSAID) that directly targets cyclooxygenase-2, COX-2, an enzyme responsible for inflammation and pain. Targeting selectivity for COX-2 reduces the risk of peptic ulceration and is the main feature of celecoxib, rofecoxib, and other members of this drug class.

Indometacin

Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins.

Mefenamic acid Chemical compound

Mefenamic acid is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs), and is used to treat mild to moderate pain. It is not widely used in the United States due to its side effects and high cost compared to other NSAIDs.

Etoricoxib Selective COX-2 Inhibitor

Etoricoxib, sold under the trade name Arcoxia, is a selective COX-2 inhibitor from McOLSON Research Laboratories. Currently it is approved in more than 80 countries worldwide but not in the US, where the Food and Drug Administration (FDA) has required additional safety and efficacy data for etoricoxib before it will issue approval.

Meloxicam

Meloxicam, sold under the brand name Mobic among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation in rheumatic diseases and osteoarthritis. It is used by mouth or by injection into a vein. It is recommended that it be used for as short a period as possible and at a low dose.

Tolmetin

Tolmetin is a nonsteroidal anti-inflammatory drug (NSAID) of the heterocyclic acetic acid derivative class. It is used primarily to reduce hormones that cause pain, swelling, tenderness, and stiffness in conditions such as osteoarthritis and rheumatoid arthritis, including juvenile rheumatoid arthritis. In the United States it is marketed as Tolectin and comes as a tablet or capsule.

Nepafenac

Nepafenac, sold under the brand name Nevanac among others, is a nonsteroidal anti-inflammatory drug (NSAID), usually sold as a prescription eye drop 0.1% solution (Nevanac) or 0.3% solution (Ilevro). It is used to treat pain and inflammation associated with cataract surgery. Nepafenac is a prodrug of amfenac, an inhibitor of COX-1 and COX-2 activity.

Meclofenamic acid

Meclofenamic acid is a drug used for joint, muscular pain, arthritis and dysmenorrhea. It is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs) and was approved by the US FDA in 1980. Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the formation of prostaglandins.

Flunoxaprofen

Flunoxaprofen, also known as Priaxim, is a chiral nonsteroidal anti-inflammatory drug (NSAID). It is closely related to naproxen, which is also an NSAID. Flunoxaprofen has been shown to significantly improve the symptoms of osteoarthritis and rheumatoid arthritis. The clinical use of flunoxaprofen has ceased due to concerns of potential hepatotoxicity.

Tenoxicam

Tenoxicam, sold under the brand name Mobiflex among others, is a nonsteroidal anti-inflammatory drug (NSAID). It is used to relieve inflammation, swelling, stiffness, and pain associated with rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and periarthritis of the shoulders or hips.

Acemetacin

Acemetacin is a non-steroidal anti-inflammatory drug (NSAID) used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain. It is manufactured by Merck KGaA under the tradename Emflex, and is available in the UK and other countries as a prescription-only drug.

Secukinumab, sold under the brand name Cosentyx, is a human IgG1κ monoclonal antibody that binds to the protein interleukin (IL)-17A, and is marketed by Novartis for the treatment of psoriasis, ankylosing spondylitis, and psoriatic arthritis. It inhibits a member of the cytokine family, interleukin 17A.

References

  1. ↑ Greenblatt DJ, Matlis R, Scavone JM, Blyden GT, Harmatz JS, Shader RI (March 1985). "Oxaprozin pharmacokinetics in the elderly". British Journal of Clinical Pharmacology. 19 (3): 373–8. doi:10.1111/j.1365-2125.1985.tb02656.x. PMC   1463728 . PMID   3986088.
  2. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN   9783527607495.
  3. ↑ Wang, Runsheng (6 Aug 2015). "Comparative efficacy of non-steroidal anti-inflammatory drugs in ankylosing spondylitis: a Bayesian network meta-analysis of clinical trials". Annals of the Rheumatic Diseases. 75 (6): 1152–1160. doi:10.1136/annrheumdis-2015-207677. PMID   26248636. S2CID   20375113.
  4. 1 2 "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.PD-icon.svgThis article incorporates text from this source, which is in the public domain.
  5. 1 2 "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020.PD-icon.svgThis article incorporates text from this source, which is in the public domain.
  6. 1 2 3 4 The NDA Pipeline 1992. Chevy Chase, MD: F-D-C Reports, Inc. 1992. pp. I-462.
  7. ↑ Oxazoles , retrieved 2015-12-07
  8. ↑ Brown, K. (July 13, 1968). "Diaryloxazole and Diarylthiazolealkanoic Acids: Two Novel Series of Non-steroidal Anti-inflammatory Agents". Nature. 219 (5150): 164. Bibcode:1968Natur.219..164B. doi: 10.1038/219164a0 . PMID   5301713. S2CID   4214027.
  9. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse Station, NJ: Merck Research Laboratories. 2001.
  10. 1 2 "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Retrieved 2015-12-02.
  11. ↑ "FDA Enforcement Report" (PDF). FDA.gov. June 24, 2009. Retrieved Dec 2, 2015.
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