Orphenadrine

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Orphenadrine
Orphenadrine.svg
Systematic (IUPAC) name
N,N-dimethyl-2-[(2-methylphenyl)- phenyl-methoxy]-ethanamine
Clinical data
Trade names Generic; many brand names worldwide[1]
AHFS/Drugs.com monograph
MedlinePlus a682162
Pregnancy
category
  • AU: B2
  • US: C (Risk not ruled out)
Legal status
Routes of
administration		 Oral, intravenous, intramuscular
Pharmacokinetic data
Bioavailability 90%
Protein binding 95%
Metabolism Hepatic demethylation
Biological half-life 13-20 hours[2]
Excretion Renal and biliary
Identifiers
CAS Number 83-98-7 YesY
ATC code M03BC01 (WHO) N04AB02
PubChem CID: 4601
IUPHAR/BPS 7251
DrugBank DB01173 YesY
ChemSpider 4440 YesY
UNII AL805O9OG9 YesY
KEGG D08305 YesY
ChEBI CHEBI:7789 YesY
ChEMBL CHEMBL900 YesY
Chemical data
Formula C18H23NO
Molecular mass 269.381 g/mol
  • O(CCN(C)C)C(c1ccccc1)c2ccccc2C
  • InChI=1S/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3 YesY
  • Key:QVYRGXJJSLMXQH-UHFFFAOYSA-N YesY
  (verify)

Orphenadrine (sold under many brand names worldwide[1]) is an anticholinergic drug of the ethanolamine antihistamine class; it is closely related to diphenhydramine. It is used to treat muscle pain and to help with motor control in Parkinson's disease, but has largely been superseded by newer drugs. It was discovered and developed in the 1940s.

As of 2015 the cost for a typical month of medication in the United States is US$25 to 50.[3]

Medical use

Orphenadrine is used to relieve pain caused by muscle injuries like strains and sprains in combination with rest and physical therapy.[4] A 2004 review found little clinical evidence for the safety or efficacy of orphenadrine for this use.[5]

Orphenadrine and other muscle relaxants are sometimes used to treat pain arising from rheumatoid arthritis but there is no evidence they are effective for that purpose.[6]

A 2003 Cochrane Review of the use of anticholinergic drugs to improve motor function in Parkinson's disease found that as a class, the drugs are useful for that purpose; it identified one single-site randomised, cross-over study of orphenadrine vs placebo.[7] Orphenadrine and other anticholinergics have largely been superseded by other drugs; they have a use in alleviating motor function symptoms, and appear to help about 20% of people with Parkinson's.[8]

Side effects

Orphenadrine has the side effects of the other common antihistamines in large part. Stimulation is somewhat more common than with other related antihistamines, and is especially common in the elderly. Common side effects include dry mouth, dizziness, drowsiness, upset stomach or vomiting, constipation, urine retention, blurred vision, and headache.[4] Its use in Parkinson's is especially limited by these factors.[7]

People with glaucoma, digestive problems like peptic ulcers or bowel obstruction, or sphincter relaxation disorders, or with enlarged prostate, bladder problems, or myasthenia gravis, should not take this drug.[9]

Pharmacology

Orphenadrine is known to have this pharmacology:

Chemistry

Orphenadrine is a methylated derivative of diphenhydramine.[18]

Preparations

Orphenadrine has been available as a citrate salt and a hydrochloride salt; in the US as of February 2016 the citrate form was available in tablets, extended release tablets, and by injection for acute use in a hospital setting.[1][19]

Orphenadrine is often available mixed with aspirin, paracetamol/acetaminophen, ibuprofen, caffeine, and/or codeine.[1]

History

George Rieveschl was a professor of chemistry at the University of Cincinnati and led a research program working on antihistamines. In 1943, one of his students, Fred Huber, synthesized diphenhydramine. Rieveschl worked with Parke-Davis to test the compound, and the company licensed the patent from him. In 1947 Parke-Davis hired him as their Director of Research. While he was there, he led the development of orphenadrine, an analog of diphenhydramine.[20]

Prior to the development of amantadine in the late 1960s and then other drugs, anticholinergics like orphenadrine were the mainstay of Parkinson's treatment.[8]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 Drugs.com international listings for orphenadrine Page accessed Feb 5, 2016
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 Medline Plus. Medline Plus entry for Orphenadrine. Page last updated December 1, 2010. Page accessed February 6, 2016]
  5. ↑ Chou R, Peterson K, Helfand M. Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. PMID 15276195
  6. ↑ Richards BL, Whittle SL, Buchbinder R. Muscle relaxants for pain management in rheumatoid arthritis. Cochrane Database Syst Rev. 2012 Jan 18;1:CD008922. PMID 22258993
  7. ↑ 7.0 7.1 Katzenschlager R, et al. Anticholinergics for symptomatic management of Parkinson's disease. Cochrane Database Syst Rev. 2003;(2):CD003735. PMID 12804486
  8. ↑ 8.0 8.1 Ivan Donaldson, C. David Marsden, Susanne Schneider. Marsden's Book of Movement Disorders. Oxford University Press, 2012. ISBN 9780192619112. Page 281
  9. ↑ Orphenadrine Citrate Extended release label Revised October 1998
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Christophe Morice and Camille Wermuth. Ring Transformations. Chapter 9 in The Practice of Medicinal Chemistry, 4th Edition. Eds. Camille Georges Wermuth, David Aldous, Pierre Raboisson, Didier Rognan. Elsevier, 2015 ISBN 9780124172135 Pages 250-251
  19. ↑ FDA listing of Orphenadrine citrate registrations. Page accessed Feb 6, 2016
  20. ↑ Walter Sneader. Drug Discovery: A History. John Wiley & Sons, 2005 ISBN 9780471899792. Page 405

External links

Retrieved from "https://infogalactic.com/w/index.php?title=Orphenadrine&oldid=722398319"