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Chloropyramine

Chloropyramine structure

CAS No:
59-32-5
Formula:
C16H20ClN3
Chemical Name:
Chloropyramine
Synonyms:
1,2-Ethanediamine,N1-[(4-chlorophenyl)methyl]-N2,N2-dimethyl-N1-2-pyridinyl-;Pyridine,2-[(p-chlorobenzyl)[2-(dimethylamino)ethyl]amino]-;1,2-Ethanediamine,N-[(4-chlorophenyl)methyl]-N′,N′-dimethyl-N-2-pyridinyl-;N1-[(4-Chlorophenyl)methyl]-N2,N2-dimethyl-N1-2-pyridinyl-1,2-ethanediamine;Avapena;Chlorneoantergan;2-[(p-Chlorobenzyl)(2-dimethylaminoethyl)amino]pyridine;Chloropyramine;Chlorpyramine;N,N-Dimethyl-N′-(p-chlorobenzyl)-N′-(2-pyridyl)ethylenediamine;N,N-Dimethyl-N′-(2-pyridyl)-N′-(4-chlorobenzyl)ethylenediamine;Halopyramine;Suprastin;Synopen;Synpen;Synopen R;N-Dimethylaminoethyl-N-p-chlorobenzyl-α-aminopyridine;Chloropyribenzamine;Allergan S;NSC 241038;Subrestin;N′-[(4-Chlorophenyl)methyl]-N,N-dimethyl-N′-pyridin-2-yl-ethane-1,2-diamine;N-[(4-Chlorophenyl)methyl]-N-[2-(dimethylamino)ethyl]pyridine-2-amine
Categories:
Active Pharmaceutical Ingredients > Antiallergic Drugs

Description

Solid

N'-[(4-chlorophenyl)methyl]-N,N-dimethyl-N'-(2-pyridinyl)ethane-1,2-diamine is an aminopyridine.|Chlorpyramine is a first generation antihistamine used in Eastern European countries to treat bronchial asthma as well as allergice rhinitis, allergic conjunctivitis, and other allergic reactions. It is also indicated for Quincke's edema, allergic reactions to insect bites, food and drug allergies, and anaphylactic shock.

Chloropyramine Basic Attributes

Molecular Weight：

289.8

Exact Mass：

289.80

EC Number：

200-421-1

UNII：

2K3L8O9SOV

NSC Number：

241038

DSSTox ID：

DTXSID50207729

ATC Code：

D - Dermatologicals|R - Respiratory system

Characteristics

PSA：

19.4

XLogP3：

3.30320

Appearance：

Solid

Density：

1.158g/cm3

Melting Point：

<25 °C

Boiling Point：

154.5 °C

Flash Point：

203.9ºC

Refractive Index：

1.6

Water Solubility：

H2O: Insoluble

Safety Information

Precautionary statement(s)：

P261, P264, P270, P271, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P342+P311, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P342+P311, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Oral (LD50): Acute: 142 mg/kg [Rat]. 135 mg/kg [Mouse]. DUST (LC50): Acute: 209 mg/m 2 hours [Rat].

Drug Information

Drug Indication：

For the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions.

Pharmacology：

Chlorpyramine is a competitive reversible H1 receptor antagonist. This inhibits vasodilation, increases in vascular permeability, and tissue edema associated with histamine release. In addition, chloropyramine has some anticholinergic properties. These effects, along with its ability to pass through the blood-brain barrier lead to side effects such as drowsiness, weakness, vertigo, fatigue, dryness in the mouth, constipation, and rarely - visual disturbances and increase of intraocular pressure.

MeSH：

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

Mechanism of Action：

Chloropyramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

MeSH Entry Terms：

Avapena

Chloropyramine Use and Manufacturing

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:289.80
XLogP3:3.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:289.1345753
Monoisotopic Mass:289.1345753
Topological Polar Surface Area:19.4
Heavy Atom Count:20
Complexity:264
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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