BUDIPINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27N.ClH
Molecular Weight	329.907
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)(C)N1CCC(CC1)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=USUUKNCFNKZGEY-UHFFFAOYSA-N

InChI=1S/C21H27N.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H27N
Molecular Weight	293.4458
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10370904 | DOI 10.1007/978-3-7091-6360-3 , Przuntek H., Müller T., 'Diagnosis and Treatment of Parkinson’s Disease - State of the Art' (2013), p. 88, Retrieved from https://books.google.com/books?id=G6DzCAAAQBAJ&dq

Budipine is an antiparkinsonian drug, which was developed by Byk Gulden (now Takeda) for the treatment of Parkinson's disease. The drug has multiple mechanisms of action: it was found to interfere with dopamine biosynthesis, mainly by inhibiting MAO-B enzyme and stimulating aromatic L-amino acid decarboxylase. Also the drug inhibits the dopamine re-uptake and has weak affinity to NMDA and muscarinic receptors. Budipine passes the blood-brain barrier, is metabolized by hydroxylation, and is excreted by both in urine and feces within 24 h.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Amine oxidase [flavin-containing] B 11 Target ID: P27338 Gene ID: 4129.0 Gene Symbol: MAOB Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10370904	Inhibitor 8297	5.0 µM [IC50]
Sodium-dependent dopamine transporter 42 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10370904	Blocker 537	11.0 µM [IC50]
Aromatic-L-amino-acid decarboxylase 5 Target ID: P20711 Gene ID: 1644.0 Gene Symbol: DDC Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10370904	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.medikamente-per-klick.de/images/ecommerce/08/44/08449633_2011-04_de_o.pdf	Primary		Approved 8429	PARKINSAN Approved Use For combination therapy of Parkinson's disease. Launch Date 8.5207679E11

PubMed

Title	Date	PubMed
[Synthesis, physical-chemical properties and pharmacologically-oriented screening studies on budipine and related 4,4-diphenylpiperidines].	1984	6539602
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease.	2000 Sep	11199819
Non-dopaminergic drug treatment of Parkinson's disease.	2001 Apr	11336607
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.	2001 Aug	11505218
[Monotherapy of Parkinson's disease with budipine. A double blind comparison with amantadine].	2001 Feb	11253562
Dose linearity and steady state pharmacokinetics of the new antiparkinson agent budipine after oral administration.	2001 Jun	11430634
Sudden daytime sleep onset in Parkinson's disease: polysomnographic recordings.	2001 May	11391745
Neuroprotection by NMDA receptor antagonists in a variety of neuropathologies.	2001 Sep	11554551
Budipine provides additional benefit in patients with Parkinson disease receiving a stable optimum dopaminergic drug regimen.	2002 May	12020263
[Dopaminergic agents, COMT inhibitors or amantadine? Proper treatment for your Parkinson patient].	2002 May 6	12070848
Evaluation of possible pro- or antioxidative properties and of the interaction capacity with the microsomal cytochrome P450 system of different NMDA-receptor ligands and of taurine in vitro.	2003 Jun	12877357
[Diagnosis and treatment of Parkinson's syndrome. What is important for the general practitioner?].	2003 May 26	14579497
Drug binding to aromatic residues in the HERG channel pore cavity as possible explanation for acquired Long QT syndrome by antiparkinsonian drug budipine.	2003 Nov	14557918
Synergism between topiramate and budipine in refractory status epilepticus in the rat.	2004 Nov	15509230
Antiapoptotic effects of budipine.	2004 Oct	15480843
Pharmacotherapy of Parkinson's disease in Germany.	2005 Aug	15765268
Efficacy of budipine and placebo in untreated patients with Parkinson's disease.	2005 Aug	15583956
Effects of amantadine and budipine on antidepressant drug-evoked changes in extracellular 5-HT in the frontal cortex of freely moving rats.	2005 Jul	15834446
The anti-Parkinson drug budipine is exported actively out of the brain by P-glycoprotein in mice.	2005 Jul 22-29	15936515
Efficacy and safety of high-dose cabergoline in Parkinson's disease.	2006 Jan	16367894
[Diagnosis and therapy of idiopathic Parkinson's disease].	2006 May 15	20104716
Budipine in Parkinson's tremor.	2006 Oct 25	16784759
Effects of amantadine and budipine on antidepressant drug-evoked changes in extracellular dopamine in the frontal cortex of freely moving rats.	2006 Oct 30	16996043
Paradoxical aspects of parkinsonian tremor.	2008 Jan 30	17973325
A new strategy for antidepressant prescription.	2010	21151361
[On the role of MAO B inhibitors and NMDA antagonists in the therapy of Parkinson's disease].	2010 Mar	20195940

Patents

Sample Use Guides

In Vivo Use Guide

The dosage is determined individually. The treatment should start with 3 times daily 10 mg budipine hydrochloride. If necessary, the daily dose should be increased at the earliest after 1 week to 3 x 20 mg budipine hydrochloride or 2 x 30 mg budipine hydrochloride.

Route of Administration: Oral

In Vitro Use Guide

10(-7), 10(-8), 10(-9) mol/l of budipine significantly reduced release of TNF-alpha and Il-6 in PBMC and decreased apoptotic cell death after 50 hours and 74 hours in the SH-SY 5Y cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:58:45 UTC 2023` Edited by `admin` on `Fri Dec 15 15:58:45 UTC 2023`
Record UNII	NBF4Q9307Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUDIPINE HYDROCHLORIDE

Common Name

English

PARKINSAN

Brand Name

English

BUDIPINE HYDROCHLORIDE [MI]

Common Name

English

1-TERT-BUTYL-4,4-DIPHENYLPIPERIDINIUM CHLORIDE

Systematic Name

English

Budipine Hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

MERCK INDEX

m2747