Budipine

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Budipine
Budipine.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • 1-tert-butyl-4,4-diphenylpiperidine [1]
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.055.494 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H27N
Molar mass 293.454 g·mol−1
3D model (JSmol)
  • 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 Yes check.svgY
  • Key:QIHLUZAFSSMXHQ-UHFFFAOYSA-N Yes check.svgY
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Budipine (brand name Parkinsan) is an antiparkinson agent marketed for the treatment of Parkinson's disease. [2] [3] [4]

Contents

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]

It is an hERG blocker and can produce long QT syndrome as a side effect. [9]

Analogues include prodipine and medipine. [10] [11]

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. [12] This method of synthesis enables a 99% yield of product.

Thieme Synthesis: Budipine synthesis.svg
Thieme Synthesis:

4-Phenyl-1-t-butyl-4-piperidinol, [14] (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. 1 2 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. 1 2 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. ↑ Scholz EP, Zitron E, Kiesecker C, Lueck S, Kathöfer S, Thomas D, Weretka S, Peth S, Kreye VA, Schoels W, Katus HA, Kiehn J, Karle CA (November 2003). "Drug binding to aromatic residues in the HERG channel pore cavity as possible explanation for acquired Long QT syndrome by antiparkinsonian drug budipine". Naunyn Schmiedebergs Arch Pharmacol. 368 (5): 404–414. doi:10.1007/s00210-003-0805-5. PMID   14557918.
  10. ↑ Russ H, Pindur U, Przuntek H (1986). "The interaction of 1-alkyl-4,4-diphenylpiperidines with the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine receptor binding site". J Neural Transm. 65 (3–4): 157–166. doi:10.1007/BF01249078. PMID   3011983. Other representatives of this class of substances, the 1-alkyl-4,4-diphenylpiperidines, such as, e.g., the 1-isopropyl analogue (prodipine) or the 1-methyl analogue (medipine) have similar pharmacological properties including marked tremorin and reserpin antagonism (Schaefer et al., 1984). The mechanism of action of the 1-alkyl-4,4- diphenylpiperidines is not yet understood in detail.
  11. ↑ Fonne-Pfister R, Meyer UA (October 1988). "Xenobiotic and endobiotic inhibitors of cytochrome P-450dbl function, the target of the debrisoquine/sparteine type polymorphism". Biochem Pharmacol. 37 (20): 3829–3835. doi:10.1016/0006-2952(88)90063-9. PMID   2903741. Budipine (1-t-butyl-4,4-diphenylpiperidine) (Parkinson's disease treatment); Prodipine (1-isopropyl-4,4-diphenylpiperidine); Medipine (1-methyl-4,4-diphenylpiperidine)
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ "4-Phenyl-1-t-butyl-4-piperidinol". PubChem. U.S. National Library of Medicine. CID:20536606.
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