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Chlorquinaldol

Chlorquinaldol structure

CAS No:
72-80-0
Formula:
C10H7Cl2NO
Chemical Name:
Chlorquinaldol
Synonyms:
8-Quinolinol,5,7-dichloro-2-methyl-;5,7-Dichloro-2-methyl-8-quinolinol;Chlorquinaldol;5,7-Dichloro-8-hydroxyquinaldine;5,7-Dichloro-2-methyl-8-hydroxyquinoline;5,7-Dichloro-8-quinaldinol;Gyno-Sterosan;Siogene;Siosteran;Sterosan;Steroxin;Saprosan;Siogen;Siogeno;Siogenon;Chlorchinaldol;Afungil;Siogenal;Sterozan;Vagisteran;Chloquinan;Siosept;Florabina;Chlorguinaldon;Chlorchinaldin;Acnosan;5,7-Dichloro-8-hydroxy-2-methylquinoline;Hydroxydichloroquinaldinol;Gynotherax;Quesil;5,7-Dichloro-2-styrylquinoline;37264-93-0
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Chlorquinaldol is a mono-hydroxyquinoline, is an antifungal and antibacterial, used for topical treatment of skin conditions and vaginal infections.

Chlorquinaldol is 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. It has a role as an antibacterial drug, an antiseptic drug and an antiprotozoal drug. It is an organochlorine compound and a monohydroxyquinoline.|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.|Chlorquinaldol is a Standardized Chemical Allergen. The physiologic effect of chlorquinaldol is by means of Increased Histamine Release, and Cell-mediated Immunity.|Local anti-infective agent used for skin, gastrointestinal, and vaginal infections with fungi, protozoa, and certain bacteria. In animals, it causes central nervous system damage and is not administered parenterally. It is also used as antiseptic, fungistat, or deodorant.

Chlorquinaldol Basic Attributes

Molecular Weight：

228.07

Exact Mass：

228.07

EC Number：

200-789-3

UNII：

D6VHC87LLS

NSC Number：

755830

DSSTox ID：

DTXSID3048998

ATC Code：

D - Dermatologicals|G - Genito urinary system and sex hormones|P - Antiparasitic products, insecticides and repellents|R - Respiratory system

HScode：

2933499090

Characteristics

PSA：

33.1

XLogP3：

3.5

Appearance：

yellow to brown crystalline powder

Density：

1.5±0.1 g/cm3

Melting Point：

114.5 °C

Boiling Point：

350.7°C at 760 mmHg

Flash Point：

165.9±26.5 °C

Refractive Index：

1.679

Water Solubility：

Insoluble

Storage Conditions：

2-8°C

Safety Information

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

22-36/37/38-23/24/25

safety instructions：

26-36-36/37/39-45

RTECS Number：

VC5600000

Marks：

Xn,T

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (98.53%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 68 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Oral LD50 (rat) - 660mg/kg

Drug Information

Drug Indication：

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.

Pharmacology：

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

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

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.|Chlorquinadol is primarily excreted in the urine as the sulfate form. About 2% is excreted as the parent drug.

Metabolism/Metabolites：

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

Mechanism of Action：

The mechanism by which Chlorquinaldol exerts it's bacteriocidal effect is unknown. 8-hydroxyquinolines are known to be bidentate chelators of several metal ions which act as critical enzyme cofactors. However, the addition of exogenous metal ions does not appear to alter the minimum inhibitory concentration for mycobacterium tuberculosis suggesting that the primary mechanism does not rely on chelation.

MeSH Entry Terms：

5,7 Dichloro 2 methyl 8 quinolinol

Chlorquinaldol Use and Manufacturing

antiinfectant, antifungal

Computed Properties

Molecular Weight:228.07
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:226.9904692
Monoisotopic Mass:226.9904692
Topological Polar Surface Area:33.1
Heavy Atom Count:14
Complexity:214
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Unspecified

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Chloroquinaldol
Manufacturer	Yabao Pharmaceutical Group Co., Ltd.

Chlorquinaldol-Promestriene vaginal tablets
Ingredients	The main ingredients are chloroquine and promestriene.
Indication	Not yet clear.
Specifications	Chloroquinaldol 0.2g, promestriene 10mg.
Manufacturer	Bei Jing Scrianen Pharmaceutical Co., Ltd.

Chlorquinaldol-Promestriene vaginal tablets
Ingredients	The main ingredients are chloroquine and promestriene.
Indication	Not yet clear.
Specifications	Chloroquinaldol 0.2g, promestriene 10mg.
Manufacturer	Bei Jing Scrianen Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Yabao Pharmaceutical Group Co., Ltd.

China
Active
Beijing Jinchengtaier Pharmaceutical Co., Ltd.

China
Active
Bei Jing Scrianen Pharmaceutical Co., Ltd.

China
Active

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5,7-Dichloro-8-hydroxyquinaldine CAS72-80-0

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