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Buclizine
Identification
- Name
- Buclizine
- Accession Number
- DB00354
- Description
Buclizine is an antihistamine medication with both antiemetic and anticholinergic effects 5, belonging to the piperazine derivative family of drugs. It was manufactured by Stuart Pharms and initially approved by the FDA in 1957.4 Following this, it was touted to be effective as an appetite stimulant in children when administered in the syrup form, however, this indication has not been validated.1 In addition to the above conditions, buclizine has been studied in the treatment of migraine attacks and in the treatment of nausea and vomiting during pregnancy. 2,3
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Buclizine (DB00354)
- Weight
- Average: 433.028
Monoisotopic: 432.233226773 - Chemical Formula
- C28H33ClN2
- Synonyms
- 1-(p-tert-Butylbenzyl)-4-(4-chloro-alpha-phenylbenzyl)piperazine
- Buclizina
- Buclizine
- Buclizinum
Pharmacology
- Indication
For prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness and vertigo (dizziness caused by other medical problems).
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Buclizine is a piperazine-derivative antihistamine used as an antivertigo/antiemetic agent. Buclizine is used in the prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness. Additionally, it has been used in the management of vertigo in diseases affecting the vestibular apparatus. Although the mechanism by which buclizine exerts its antiemetic and antivertigo effects has not been fully elucidated, its central anticholinergic properties are partially responsible. The drug depresses labyrinth excitability and vestibular stimulation, and it may affect the medullary chemoreceptor trigger zone. It also possesses anticholinergic, antihistaminic, central nervous system depressant, and local anesthetic effects.
- Mechanism of action
Vomiting (emesis) is essentially a protective mechanism for removing irritant or otherwise harmful substances from the upper GI tract. Emesis or vomiting is controlled by the vomiting centre in the medulla region of the brain, an important part of which is the chemotrigger zone (CTZ). The vomiting centre possesses neurons which are rich in muscarinic cholinergic and histamine containing synapses. These types of neurons are especially involved in transmission from the vestibular apparatus to the vomiting centre. Motion sickness principally involves overstimulation of these pathways due to various sensory stimuli. Hence the action of buclizine which acts to block the histamine receptors in the vomiting centre and thus reduce activity along these pathways. Furthermore since buclizine possesses anti-cholinergic properties as well, the muscarinic receptors are similarly blocked.
Target Actions Organism AHistamine H1 receptor antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistweak inhibitorHumans - Absorption
Rapidly absorbed following oral administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hepatic.
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Buclizine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcebutolol The risk or severity of QTc prolongation can be increased when Buclizine is combined with Acebutolol. Acetazolamide Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Buclizine. Acetophenazine Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Buclizine. Aclidinium The risk or severity of adverse effects can be increased when Buclizine is combined with Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Buclizine is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Buclizine is combined with Adenosine. Agomelatine Agomelatine may increase the central nervous system depressant (CNS depressant) activities of Buclizine. Ajmaline The risk or severity of QTc prolongation can be increased when Buclizine is combined with Ajmaline. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Buclizine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Buclizine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Buclizine hydrochloride 58FQD093NU 129-74-8 SDBHDSZKNVDKNU-UHFFFAOYSA-N - International/Other Brands
- Bucladin / Bucladin-S / Longifene Syrup (Novartis India)
Categories
- ATC Codes
- R06AE51 — Buclizine, combinations
- R06AE — Piperazine derivatives
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Phenylpropanes / Phenylmethylamines / Benzylamines / N-alkylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Azacyclic compounds / Organopnictogen compounds show 2 more
- Substituents
- 1,4-diazinane / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzylamine / Chlorobenzene / Diphenylmethane show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monochlorobenzenes, N-alkylpiperazine (CHEBI:3205)
Chemical Identifiers
- UNII
- 1178B2VD9B
- CAS number
- 82-95-1
- InChI Key
- MOYGZHXDRJNJEP-UHFFFAOYSA-N
- InChI
- InChI=1S/C28H33ClN2/c1-28(2,3)25-13-9-22(10-14-25)21-30-17-19-31(20-18-30)27(23-7-5-4-6-8-23)24-11-15-26(29)16-12-24/h4-16,27H,17-21H2,1-3H3
- IUPAC Name
- 1-[(4-tert-butylphenyl)methyl]-4-[(4-chlorophenyl)(phenyl)methyl]piperazine
- SMILES
- CC(C)(C)C1=CC=C(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)C=C1
References
- General References
- Babu TA: Buclizine is back again! This time as a pediatric appetite stimulant. Indian J Pharmacol. 2011 Apr;43(2):219. doi: 10.4103/0253-7613.77383. [PubMed:21572667]
- Adam EI: A treatment for the acute migraine attack. J Int Med Res. 1987 Mar-Apr;15(2):71-5. doi: 10.1177/030006058701500202. [PubMed:3556262]
- DURHAM MP: Clinical trial of buclizine hydrochloride for vomiting of pregnancy. Br Med J. 1956 Dec 1;2(5004):1276-7. doi: 10.1136/bmj.2.5004.1276. [PubMed:13374321]
- FDA approval: Buclizine [Link]
- HMDB: Buclizine [Link]
- External Links
- Human Metabolome Database
- HMDB0014498
- KEGG Drug
- D07547
- KEGG Compound
- C07777
- PubChem Compound
- 6729
- PubChem Substance
- 46507608
- ChemSpider
- 6473
- 59636
- ChEBI
- 3205
- ChEMBL
- CHEMBL1201271
- Therapeutic Targets Database
- DAP001076
- PharmGKB
- PA164748223
- Wikipedia
- Buclizine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Stuart pharmaceuticals div ici americas
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Syrup Oral 0.12 g Tablet, coated Oral 25 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 218 °C Not Available logP 7.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000246 mg/mL ALOGPS logP 6.16 ALOGPS logP 7.42 ChemAxon logS -6.2 ALOGPS pKa (Strongest Basic) 8.04 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 6.48 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 133.02 m3·mol-1 ChemAxon Polarizability 50.93 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9298 Blood Brain Barrier + 0.9382 Caco-2 permeable + 0.6056 P-glycoprotein substrate Substrate 0.8092 P-glycoprotein inhibitor I Inhibitor 0.9051 P-glycoprotein inhibitor II Non-inhibitor 0.5415 Renal organic cation transporter Inhibitor 0.6819 CYP450 2C9 substrate Non-substrate 0.8508 CYP450 2D6 substrate Non-substrate 0.6699 CYP450 3A4 substrate Substrate 0.5976 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9502 CYP450 2D6 inhibitor Non-inhibitor 0.7104 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5546 Ames test Non AMES toxic 0.8885 Carcinogenicity Non-carcinogens 0.8723 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5190 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7081 hERG inhibition (predictor II) Inhibitor 0.8779
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-014j-4930000000-3910923ac39cbf7127f8 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistWeak inhibitor
- Curator comments
- Studies show that the inhibitory action is weak.
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Reference Module in Biomedical Sciences (2017) by Henry I. Jacoby [Link]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51
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