DrugBank: Chloropyramine (DB08800)

targets (1)

Identification

Name

Chloropyramine

Accession Number

DB08800 (DB07523)

Type

small molecule

Groups

approved

Description

Chloropyramine is a first generation antihistamine drug approved in some Eastern European countries for the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. Related indications for clinical use include Quincke’s edema, allergic reactions to insect bites, food and drug allergies, and anaphylactic shock.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Anaphylline
Chlorpyramine
Chlorpyraminum
Halopyramine

Salts

Not Available

Brand names

Name	Company
Avapena
Suprastin
Synopen
Synpen

Brand mixtures

Not Available

Categories

Anti-Allergic Agents
Antihistamines

CAS number

59-32-5

Weight

Average: 289.803
Monoisotopic: 289.134575362

Chemical Formula

C₁₆H₂₀ClN₃

InChI Key

InChIKey=ICKFFNBDFNZJSX-UHFFFAOYSA-N

InChI

InChI=1S/C16H20ClN3/c1-19(2)11-12-20(16-5-3-4-10-18-16)13-14-6-8-15(17)9-7-14/h3-10H,11-13H2,1-2H3

Plain Text

IUPAC Name

N-[(4-chlorophenyl)methyl]-N-[2-(dimethylamino)ethyl]pyridin-2-amine

SMILES

CN(C)CCN(CC1=CC=C(Cl)C=C1)C1=CC=CC=N1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

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

Pharmacodynamics

Chloropyramine is known as a competitive reversible H1-receptor antagonist (also known as an H1 inverse agonist), meaning that it exerts its pharmacological action by competing with histamine for the H1 subtype histamine receptor. By blocking the effects of histamine, the drug inhibits the vasodilation, increased vascular permeability, and tissue edema associated with histamine release in the tissue. In addition, chloropyramine has some anticholinergic properties. Chloropyramine's anticholinergic properties and the fact that it can pass through the blood-brain barrier are linked to its clinical side effects: drowsiness, weakness, vertigo, fatigue, dryness in the mouth, constipation, and rarely - visual disturbances and increase of intraocular pressure.

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

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

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	< 25 °C	PhysProp
boiling point	154.5 °C at 2.00E-01 mm Hg	PhysProp
water solubility	Insoluble	MSDS

Predicted Properties

Property	Value	Source
water solubility	4.41e-01 g/l	ALOGPS
logP	3.79	ALOGPS
logP	3.81	ChemAxon
logS	-2.8	ALOGPS
pKa (strongest basic)	8.76	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	3	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	19.37	ChemAxon
rotatable bond count	6	ChemAxon
refractivity	86.08	ChemAxon
polarizability	32.25	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D07195
ChemSpider	23628
PharmGKB	PA165958419
HET	C4C

ATC Codes

D04AA09
R06AC03

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (49.4 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Histamine H1 receptor Pharmacological action: yes Actions: antagonist 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system Organism class: human UniProt ID: P35367 Gene: HRH1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Budihna M, Drevensek G, Burjak M, Kocijancic S: Effects of chloropyramine and famotidine on postischaemic and posthypoxic myocardial damage in isolated rat hearts. Pflugers Arch. 1996;431(6 Suppl 2):R217-8. Pubmed

Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out

Gene: HRH1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Budihna M, Drevensek G, Burjak M, Kocijancic S: Effects of chloropyramine and famotidine on postischaemic and posthypoxic myocardial damage in isolated rat hearts. Pflugers Arch. 1996;431(6 Suppl 2):R217-8. Pubmed

Comments

Drug created on October 14, 2010 14:21 / Updated on February 08, 2013 16:27