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Buclizine

Buclizine structure

CAS No:
82-95-1
Formula:
C28H33ClN2
Chemical Name:
Buclizine
Synonyms:
Piperazine,1-[(4-chlorophenyl)phenylmethyl]-4-[[4-(1,1-dimethylethyl)phenyl]methyl]-;Piperazine,1-(p-tert-butylbenzyl)-4-(p-chloro-α-phenylbenzyl)-;1-[(4-Chlorophenyl)phenylmethyl]-4-[[4-(1,1-dimethylethyl)phenyl]methyl]piperazine;AH 2526;Buclizine;1-(p-tert-Butylbenzyl)-4-(p-chloro-α-phenylbenzyl)piperazine;1-(p-Chlorobenzhydryl)-4-(p-tert-butylbenzyl)-diethylenediamine;1-(p-Chlorobenzhydryl)-4-(p-tert-butylbenzyl)-piperazine;1-(p-Chloro-α-phenylbenzyl)-4-(p-tert-butylbenzyl)piperazine;Histabuticine;Histabutyzine;Histabutizine;Buclifen;Aphilan R base;Posdel;Postafen;Hitabutyzyne;1-(4-(tert-Butyl)benzyl)-4-((4-chlorophenyl)(phenyl)methyl)piperazine
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

ChEBI: An N-alkylpiperazine carrying (4-chlorophenyl)(phenyl)methyl and 4-tert-butylbenzyl groups.

Liquid

Buclizine is an N-alkylpiperazine carrying (4-chlorophenyl)(phenyl)methyl and 4-tert-butylbenzyl groups. It has a role as an antiemetic, a cholinergic antagonist, a histamine antagonist, a local anaesthetic and a central nervous system depressant. It is a N-alkylpiperazine and a member of monochlorobenzenes. It is a conjugate base of a buclizine(2+).|Buclizine is an antihistamine medication with both antiemetic and anticholinergic effects, belonging to the piperazine derivative family of drugs. It was manufactured by Stuart Pharms and initially approved by the FDA in 1957. 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. 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.

Buclizine Basic Attributes

Molecular Weight：

433.036

Exact Mass：

433.03

EC Number：

201-448-1

UNII：

UFN4445AF2|1178B2VD9B

DSSTox ID：

DTXSID0022694

ATC Code：

R - Respiratory system

HScode：

2933599090

Characteristics

PSA：

6.5

XLogP3：

7.1

Appearance：

Liquid

Density：

0.9970 (rough estimate)

Boiling Point：

218 °C

Water Solubility：

2.46e-04 g/L

Drug Information

Drug Indication：

For prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness and vertigo (dizziness caused by other medical problems).

Pharmacology：

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.

MeSH：

Drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only. (See all compounds classified as Histamine Antagonists.)

Absorption：

Rapidly absorbed following oral administration.

Metabolism/Metabolites：

Hepatic.

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.

MeSH Entry Terms：

1-((4-chlorophenyl)phenylmethyl)-4-((4-(1,1-dimethylethyl)phenyl)methyl)piperazine

Buclizine Use and Manufacturing

Uses

Buclizine is an antinauseant.

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:433.0
XLogP3:7.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:432.2332268
Monoisotopic Mass:432.2332268
Topological Polar Surface Area:6.5
Heavy Atom Count:31
Complexity:514
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Paraformaldehyde

Aluminum trichloride hexahydrate