Chloropyramine

Chloropyramine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	C;
Routes of; administration	By mouth, intramuscular, topical
Drug class	First-generation antihistamine
ATC code	D04AA09 (WHO) R06AC03 (WHO);
Legal status
Legal status	By mouth: OTC, Injection: Rx-only (RU);
Pharmacokinetic data
Bioavailability	~100%
Metabolism	Extensive hepatic
Onset of action	15–30 min (oral)
Elimination half-life	~14 hours
Excretion	Kidney
Identifiers
	IUPAC name N'-[(4-chlorophenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine;
CAS Number	59-32-5 ;
PubChem CID	25295;
DrugBank	DB08800 ;
ChemSpider	23628 ;
UNII	2K3L8O9SOV;
KEGG	D07195 ;
ChEMBL	ChEMBL1194287 ;
CompTox Dashboard (EPA)	DTXSID50207729 ;
ECHA InfoCard	100.000.383
Chemical and physical data
Formula	C16H20ClN3
Molar mass	289.81 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)CN(c2ncccc2)CCN(C)C;
	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 ; Key:ICKFFNBDFNZJSX-UHFFFAOYSA-N ;
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Chloropyramine is a first-generation antihistamine drug approved in several Eastern European countries such as Russia for the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. Related indications for clinical use include angioedema, allergic reactions to insect bites, food and drug allergies, and anaphylactic shock.

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. The H₁ antagonistic properties of chloropyramine can be used by researchers for the purposes of blocking the effects of histamine on cells and tissues. In addition, chloropyramine has some anticholinergic properties.^[1]

Chloropyramine's anticholinergic properties and the fact that it can pass through the blood–brain barrier are linked to its clinical side effects such as drowsiness, weakness, vertigo, fatigue, dry mouth, constipation, and rarely — visual disturbances and increase of intraocular pressure.

^ ^a ^b "Chloropyramine Tablets for Oral Use. Prescribing Information". State Register of Medicines (in Russian). Ozon OOO. Retrieved 5 January 2016.
^ ^a ^b ^c "Хлоропирамин (Chloropyraminum)" (in Russian).

[PI-1] "Chloropyramine Tablets for Oral Use. Prescribing Information". State Register of Medicines (in Russian). Ozon OOO. Retrieved 5 January 2016.

[lsgeotar-2] "Хлоропирамин (Chloropyraminum)" (in Russian).

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