CHLOROQUINE

CHLOROQUINE Properties

Melting point	87°
Boiling point	475.41°C (rough estimate)
Density	1.0500 (rough estimate)
refractive index	1.6010 (estimate)
storage temp.	2-8°C(protect from light)
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
pka	pKa 8.4(H2O t = 20) (Uncertain)
color	White to Light Brown
Stability	Stable, but light sensitive. Incompatible with strong oxidizing agents.
IARC	3 (Vol. 13, Sup 7) 1987
EPA Substance Registry System	1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl- (54-05-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264-P270-P301+P312-P330-P501
Toxicity	LD50 oral in rat: 330mg/kg

CHLOROQUINE Chemical Properties,Uses,Production

Description

Chloroquine is the most effective of the hundreds of 4-aminoquinolines synthesized and tested during World War II as potential antimalarials. Structure–activity relationships demonstrated that the chloro at the 8-position increased activity, whereas alkylation at C-3 and C-8 diminished activity. The replacement of one of its N-ethyl groups with an hydroxyethyl produced hydroxychloroquine, a compound with reduced toxicity that is rarely used today except in cases of rheumatoid arthritis.

Chemical Properties

solid

Uses

Chloroquine used in the treatment of malaria and MDR-strains. It is a COVID19-related research product.

Indications

Chloroquine (Aralen) is one of several 4-aminoquinoline derivatives that display antimalarial activity. Chloroquine is particularly effective against intraerythrocytic forms because it is concentrated within the parasitized erythrocyte. This preferential drug accumulation appears to occur as a result of specific uptake mechanisms in the parasite. Chloroquine appears to work by intercalation with DNA, inhibition of heme polymerase or by interaction with Ca++–calmodulinmediated mechanisms. It also accumulates in the parasite’s food vacuoles, where it inhibits peptide formation and phospholipases, leading to parasite death.

Definition

ChEBI: An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin erupti ns, and rheumatoid arthritis.

World Health Organization (WHO)

Chloroquine, a 4-aminoquinoline derivative, was introduced in the 1940s for the treatment and prophylaxis of malaria. It was subsequently found to be effective in higher and prolonged dosage in the treatment of lupus erythematosus, rheumatoid arthritis and nephritis. In the early 1970s its use in these latter conditions was largely discontinued when it was found that prolonged daily administration at high dosage was associated with cases of retinopathy resulting from local deposition of the compound. Chloroquine however remains a valuable drug. It can be used continuously at the dosages required for malaria prophylaxis for as long as five years without risk of undue accumulation and it is included in the WHO Model List of Essential Drugs for both its antimalarial and antiamoebic activity. (Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO Expert Committee, 722, , 1985)

Antimicrobial activity

Chloroquine accumulates 300-fold in infected erythrocytes and acts against the early erythrocytic stages of all four species of Plasmodium that cause human malaria. It is also active against the gametocytes of P. vivax, P. ovale and P. malariae, but not against the hepatic stages or mature erythrocytic schizonts and merozoites.

Acquired resistance

Resistance of P. falciparum is widespread and has become a major problem. The mechanism appears to be either decreased uptake or increased efflux of the drug by the parasite, or both. Changes in genes encoding a P-glycoprotein homolog, Pfmdr1, and another putative transporter, Pfcrt, are associated with resistance. Reversal of resistance with, for example, verapamil or probenecid has been demonstrated in experimental models, but human trials have been disappointing. Chloroquine-resistant P. vivax has been reported in South America and South East Asia.

Hazard

Toxic by ingestion. Questionable carcinogen.

Pharmaceutical Applications

A synthetic 4-aminoquinoline, formulated as the phosphate or sulfate for oral administration and as the hydrochloride or sulfate for parenteral use. The salts are soluble in water.

Mechanism of action

The absorption of chloroquine from the gastrointestinal tract is rapid and complete. The drug is distributed widely and is extensively bound to body tissues, with the liver containing 500 times the blood concentration. Such binding is reflected in a large volume of distribution (Vd). Desethylchloroquine is the major metabolite formed following hepatic metabolism, and both the parent compound and its metabolites are slowly eliminated by renal excretion.The half-life of the drug is 6 to 7 days.

Pharmacokinetics

Oral absorption: 80–90%
C_max 300 mg oral: 0.25 mg/L after 1–6 h
Plasma half-life: c. 9 days (mean)
Volume of distribution: 200 L/kg
Plasma protein binding: 50–70%
There is extensive tissue binding and a high affinity for melanin- containing tissues. Chloroquine is extensively metabolized to a biologically active monodesethyl derivative that forms about 20% of the plasma level of the drug. The mean elimination half-life results from an initial phase (3–6 days), a slow phase (12–14 days) and a terminal phase (40 days). Renal clearance is about 50% of the dose.

Clinical Use

The drug is effective against all four types of malaria with the exception of chloroquine-resistant P. falciparum. Chloroquine destroys the blood stages of the infection and therefore ameliorates the clinical symptoms seen in P. malariae, P. vivax, P. ovale, and sensitive P. falciparum forms of malaria. The disease will return in P. vivax and P. ovale malaria, however, unless the liver stages are sequentially treated with primaquine after the administration of chloroquine. Chloroquine also can be used prophylactically in areas where resistance does not exist. In addition to its use as an antimalarial, chloroquine has been used in the treatment of rheumatoid arthritis and lupus erythematosus, extraintestinal amebiasis, and photoallergic reactions.

Side effects

Minor side effects such as dizziness, headache, rashes, nausea and diarrhea are common. Pruritus occurs in up to 20% of Africans taking chloroquine. Long-term treatment can induce CNS effects and cumulative dosing over many years may cause retinopathy. Rarely, photosensitization, tinnitus and deafness have occurred.

Environmental Fate

The exact mechanism of action of CQ and HCQ is not completely understood but involves inhibition of DNA and RNA polymerase. They are also direct myocardial depressants that impair cardiac conduction through membrane stabilization. It is unclear how they work in autoimmune diseases.

CHLOROQUINE Preparation Products And Raw materials

Raw materials

4,7-Dichloroquinoline 2-Amino-5-diethylaminopentane

Preparation Products

Chloroquinine phosphate Chloroquine diphosphate

CHLOROQUINE Suppliers

Global( 151)Suppliers

Supplier	Tel	Country	ProdList	Advantage	Inquiry
CLEARSYNTH LABS LTD.	+91-22-45045900	Hyderabad, India	6351	58	Inquiry
A.J Chemicals	91-9810153283	New Delhi, India	6124	58	Inquiry
Triveni chemicals	08048762458	New Delhi, India	6093	58	Inquiry
Medinn Agencies	08047647335	Delhi, India	19	58	Inquiry
Jocund India Limited	09868450067	Delhi, India	2	58	Inquiry
Chandra Prabhu Pharma Services	08048372381Ext 506	Maharashtra, India	19	58	Inquiry
AYA NUTRITIONS	08048987442	Uttar Pradesh, India	1	58	Inquiry
Pharma Affiliates	172-5066494	Haryana, India	6761	58	Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd	+91-172-5066494	Haryana, India	6773	58	Inquiry
SHANDONG ZHI SHANG CHEMICAL CO.LTD	+86 18953170293	China	2931	58	Inquiry

Supplier	Advantage
CLEARSYNTH LABS LTD.	58
A.J Chemicals	58
Triveni chemicals	58
Medinn Agencies	58
Jocund India Limited	58
Chandra Prabhu Pharma Services	58
AYA NUTRITIONS	58
Pharma Affiliates	58
Pharmaffiliates Analytics and Synthetics P. Ltd	58
SHANDONG ZHI SHANG CHEMICAL CO.LTD	58

54-05-7(CHLOROQUINE)Related Search:

Hydroxychloroquine sulfate Mepacrine hydrochloride Aminoquinol QUINACRINE MUSTARD DIHYDROCHLORIDE Chloroquine diphosphate

Hydroxychloroquine Chloroquine sulphate BP2000,chloroquine sulfate CHLOROQUINE 4,7-DICHLOROQUINOLINE CHLOROQUINE PHOSPHATE Didesethyl Chloroquine,Didesethyl Chloroquine Hydrochloride,BISDESETHYL CHLOROQUINE

DESETHYL HYDROXY CHLOROQUINE 7-CHLOROQUINOLINE (R)-Chloroquine Didesethyl Chloroquine-d4 Chloroquine-d4 Diphosphate Salt

Desethyl Chloroquine-d4 DESETHYL CHLOROQUINE Chloroquine Phosphate injection 322.5mg/5ml

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sn7618 Solprina Sopaquin Tanakan Tresochin Trochin W 7618 w7618 WIN 244 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl- Chloraquine Chlorochin Chlorochine Chloroquina Chloroquinium Chlorquin Cidanchin Clorochina Cocartrit Delagil Dichinalex Elestol Gontochin Heliopar Imagon Iroquine Klorokin Lapaquin Malaquin Malaren Malarex Mesylith n(4)-(7-chloro-4-quinolinyl)-n(1),n(1)-diethyl-4-pentanediamine N(sup4)-(7-chloro-4-quinolinyl)-N(sup1),N(sup1)-diethyl-1,4-pentanediamine N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine Neochin Nivachine Nivaquine Nivaquine [as sulfate] Nivaquine B nivaquineb Pfizerquine Quinachlor Quinagamin Quinagamine Quinercyl win244 4-(7-chloro-4-quinolylamino)pentyldiethylamine N⁴-[7-Chloro-4-quinolinyl]-N',N'-diethyl-1,4-pentanediamine 7-CHLORO-4-(4-DIMETHYLAMINO-1-METHYLBUTYLAMINO)QUINOLINE Chloroquine (base and/or unspecified salts) 4-(4-Diethylamino-1-methylbutylamino)-7-chloroquinoline N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diaMine 1,4-pentanediamine,n(sup4)-(7-chloro-4-quinolinyl)-n(sup1),n(sup1)-diethy 3377 RP 3377 RP opalate 4-(4-Diethylamino-1-methylbntyla-mino)-7-chloroquinoline 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-quinolin