Budipine

Budipine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 1-tert-butyl-4,4-diphenylpiperidine[1]
CAS Number
  • 57982-78-2 checkY
PubChem CID
  • 68778
ChemSpider
  • 62021 checkY
UNII
  • L9026OPI2Z
KEGG
  • D07306 checkY
ChEMBL
  • ChEMBL334491 checkY
CompTox Dashboard (EPA)
  • DTXSID20206709
ECHA InfoCard100.055.494
Chemical and physical data
FormulaC21H27N
Molar mass293.454 g·mol−1
3D model (JSmol)
  • Interactive image
  • c1(ccccc1)C3(c2ccccc2)CCN(C(C)(C)C)CC3
  • InChI=1S/C21H27N/c1-20(2,3)22-16-14-21(15-17-22,18-10-6-4-7-11-18)19-12-8-5-9-13-19/h4-13H,14-17H2,1-3H3 checkY
  • Key:QIHLUZAFSSMXHQ-UHFFFAOYSA-N checkY
  (verify)

Budipine (brand name Parkinsan) is an antiparkinson agent marketed for the treatment of Parkinson's disease.[2][3][4]

While its exact mechanism of action is not well characterized,[2] it is believed to be an NMDA receptor antagonist,[5][6] but also promoting the synthesis of dopamine.[7]

Because it provides additional benefits relative to existing treatments, it probably does not precisely mimic the mechanism of an existing known treatment.[7][8]

Synthesis

Budipine can be prepared from the 1-tert-butyl-4-piperidone [1465-76-5] directly by treatment with benzene in the presence triflic acid.[9] This method of synthesis enables a 99% yield of product.

Thieme Synthesis:[10]

4-Phenyl-1-t-butyl-4-piperidinol,[11] (1)

1-t-butyl-3-benzoyl-4-phenyl-4-piperidinol [81831-81-4] (3)

See also

References

  1. ^ Sweetman SC, ed. (2007). Martindale: The Complete Drug Reference (35th ed.). London: Pharmaceutical Press. ISBN 978-0-85369-687-2.
  2. ^ a b Reichmann H (October 2006). "Budipine in Parkinson's tremor". Journal of the Neurological Sciences. 248 (1–2): 53–55. doi:10.1016/j.jns.2006.05.039. PMID 16784759. S2CID 21540225.
  3. ^ Przuntek H, Müller T (1999). "Clinical efficacy of budipine in Parkinson's disease". Diagnosis and Treatment of Parkinson's Disease — State of the Art. Journal of Neural Transmission. Supplementa. Vol. 56. pp. 75–82. doi:10.1007/978-3-7091-6360-3_3. ISBN 978-3-211-83275-2. PMID 10370903. {{cite book}}: |journal= ignored (help)
  4. ^ "Budipine". AdisInsight. Springer Nature Switzerland AG.
  5. ^ Kornhuber J, Herr B, Thome J, Riederer P (1995). "The antiparkinsonian drug budipine binds to NMDA and sigma receptors in postmortem human brain tissue". Journal of Neural Transmission. Supplementum. 46: 131–137. PMID 8821048.
  6. ^ Palmer GC (September 2001). "Neuroprotection by NMDA receptor antagonists in a variety of neuropathologies". Current Drug Targets. 2 (3): 241–271. doi:10.2174/1389450013348335. PMID 11554551.
  7. ^ a b Przuntek H, Bittkau S, Bliesath H, Büttner U, Fuchs G, Glass J, et al. (May 2002). "Budipine provides additional benefit in patients with Parkinson disease receiving a stable optimum dopaminergic drug regimen". Archives of Neurology. 59 (5): 803–806. doi:10.1001/archneur.59.5.803. PMID 12020263.
  8. ^ Owen JC, Whitton PS (October 2006). "Effects of amantadine and budipine on antidepressant drug-evoked changes in extracellular dopamine in the frontal cortex of freely moving rats". Brain Research. 1117 (1): 206–212. doi:10.1016/j.brainres.2006.07.039. PMID 16996043. S2CID 29177107.
  9. ^ Klumpp, D. A., Garza, M., Jones, A., Mendoza, S. (1 September 1999). "Synthesis of Aryl-Substituted Piperidines by Superacid Activation of Piperidones". The Journal of Organic Chemistry. 64 (18): 6702–6705. doi:10.1021/jo990454i.
  10. ^ Schaefer H, Hackmack G, Eistetter K, Krüger U, Menge HG, Klosa J (1984). "[Synthesis, physical-chemical properties and pharmacologically-oriented screening studies on budipine and related 4,4-diphenylpiperidines]". Arzneimittel-Forschung (in German). 34 (3): 233–240. PMID 6539602.
  11. ^ "4-Phenyl-1-t-butyl-4-piperidinol". PubChem. U.S. National Library of Medicine. CID:20536606.


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