5,7-Dichloro-8-hydroxyquinaldine

Absorption

There is a high degree of variability in the extent of absorption of topically applied chorquinaldol preparations. It is reported to be between 4.2 and 23.5% of the applied dose. This is quite low compared to orally administered preparations which displayed 67.6% absorption in the same study.

Toxicity

Oral LD50 (rat) - 660mg/kg

Chemical properties

yellowish to beige-brown powder

Originator

Sterosan ,Geigy ,US ,1954

The Uses of 5,7-Dichloro-8-hydroxyquinaldine

antiinfectant, antifungal

The Uses of 5,7-Dichloro-8-hydroxyquinaldine

Chlorquinaldol is a fungistat and antibacterial agent in topical pharmaceutical preparations (5,7-dichloro-2-methyl-8-quinolinol, Sterosan).

The Uses of 5,7-Dichloro-8-hydroxyquinaldine

5,7-Dichloro-8-hydroxy-2-methylquinoline is an anti-infective agent.

Indications

Chlorquinaldol was used historically as a topical antiseptic agent for skin infections. It maintains use in European countries as a combination vaginal tablet with promestriene for use in the treatment of vaginal infections.

What are the applications of Application

5,7-Dichloro-8-hydroxy-2-methylquinoline is an anti-infective agent

Background

Chlorquinaldol was used historically as a topical antiseptic under the trade name Sterosan. It was marketed in the 1950s as an iodine-free alternative which was also unrelated to sulfa drugs or hormones. Chlorquinaldol is currently approved by the European Medicines Agency as a combination tablet with promestriene for the treatment of bacterial vaginosis.

Definition

ChEBI: A monohydroxyquinoline that is quinolin-8-ol which is substituted by a methyl group at position 2 and by chlorine at positions 5 and 7. An antifungal and antibacterial, it was formerly used for topical treatment of skin conditions and vaginal infections.

Manufacturing Process

11.1 parts of 8-hydroxy-quinaldine are dissolved in 140 parts of formic acid. Chlorine is introduced into this solution under cooling, until the increase in weight corresponds to the required quantity of chlorine and a test of the chlorination mixtures gives no more dyestuff formation with diazo-benzene in an acetic acid solution
When the chlorination is complete, the reaction mixture is poured into 1,000 parts of water and treated with a dilute sodium bisulfite solution, until no more reaction may be observed with starch potassium iodide paper. Thereby the 5,7-dichloro-8-hydroxy-quinaldine separates out in form of a weakly yellowish colored precipitate. The same is filtered off and thoroughly washed with water.After drying, 15 parts of 5,7-dichloro-8-hydroxy-quinaldine melting at 111°C to 112°C are obtained. When recrystallized from alcohol, the product is obtained in voluminous, slightly yellowish needles having the melting point of 111.5°C to 112°C.

Therapeutic Function

Antibacterial

Pharmacokinetics

Chlorquinaldol is bacteriocidal in both gram positive and gram negative bacteria. It is more effective in targeting gram positive bacteria, particularly staphylococci.

Metabolism

98% of drug is converted to the sulfate form and renally excreted.

Purification Methods

Crystallise it from EtOH. [Beilstein 21/3 V 346.]