Chinacrin-dihydrochlorid

Bezeichnung:Chinacrin-dihydrochlorid

CAS-Nr69-05-6

Englisch Name:QUINACRINE DIHYDROCHLORIDE

CBNumberCB8320579

SummenformelC23H32Cl3N3O

Molgewicht472.88

MOL-Datei69-05-6.mol

Synonyma

Mepacrinhydrochlorid

Chinacrin-dihydrochlorid

Chinacrin-dihydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	249-251℃ (Decomposition)
Dichte	1.2962 (rough estimate)
Brechungsindex	1.6300 (estimate)
storage temp.	+15C to +30C
Löslichkeit	DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
pka	pKa -6.3(H2O t undefined I not reported but low) (Uncertain)
Aggregatzustand	Yellow solid
Farbe	Light Yellow to Yellow
PH	3.0～5.0 (20g/l, 25℃)
Wasserlöslichkeit	Water: 33.33 mg/mL (70.48 mM)
Merck	14,8044
BRN	4834013
Stabilität	Stable. Incompatible with strong oxidizing agents.
EPA chemische Informationen	Quinacrine hydrochloride (69-05-6)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	36/37/39
WGK Germany	3
RTECS-Nr.	AR7875000
Toxizität	LD50 oral in rabbit: 433mg/kg

Gefahreninformationscode (GHS)

QUINACRINE DIHYDROCHLORIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
yellow crystals or powder
Verwenden
Quinacrine dihydrochloride has been used:
- in its uptake and accumulation studies in mouse lung slices using fluorescence microscope
- in the staining of ATP vesicles in mesenchymal stem cells (MSCs)
- in uptake-release assay for characterization of dense granule functionality of platelets
Verwenden
Quinacrine is a derivative of acridine that is chemically and clinically very similar to 4-aminoquinolines. It was the primary drug for prevention and therapy of malaria during World War II. Today it is rarely used for treating malaria, although it is used to treat amebiasis. Synonyms of this drug are mepacrine, atabrine, acrisuxin, and others. In treating resistant forms of malaria, tetracycline is also used in combination with pyrimethamine, sulfonamides, sulfones, and dapsone, which is widely used for treating leprosy (as a rule, in combination with pyrimethamine).
Verwenden
A non-specific PLA2 inhibitor. and acetylcholine receptor antagonist
Indications
Quinacrine is no longer used extensively as an antimalarial drug and has been largely replaced by the 4- aminoquinolines.
Trademarks
Dormison (Schering).
Antimicrobial activity
Mepacrine is active against the asexual erythrocytic stage of all four Plasmodium spp. that infect humans and the gametocytes of P. vivax and P. malariae. The enantiomers have equal antimalarial activity. It exhibits broad activity in experimental models against T. cruzi, Leishmania spp., E. histolytica, Trichomonas vaginalis, G. lamblia and Blastocystis hominis. It is also active against tapeworms.
Acquired resistance
The structural resemblance to chloroquine suggests the likelihood of cross-resistance with that drug, but evidence for this is equivocal.
Allgemeine Beschreibung
Bright yellowish needles or bright yellow powder. Odorless. pH of a 1% aqueous solution is about 4.5.. Used as an anti-malarial drug. Moderately toxic.
Air & Water Reaktionen
Water soluble.
Reaktivität anzeigen
QUINACRINE DIHYDROCHLORIDE is an acidic salt of an amine. React as a weak acid to neutralize bases.
Brandgefahr
Flash point data for QUINACRINE DIHYDROCHLORIDE are not available, but QUINACRINE DIHYDROCHLORIDE is probably combustible.
Pharmazeutische Anwendungen
A synthetic acridine derivative, formulated as the hydrochloride for oral use.
Biochem/physiol Actions
Target IC50: 4.4 μM in suppressing glibenclamide-sensitive K+-currents
Pharmakokinetik
Oral absorption: Good
C_max 100 mg oral: 50 μg/L after 1–3 h
Plasma half-life: 5 days
Plasma protein binding: 85%
There is extensive tissue binding and a six-fold concentration into leukocytes from plasma. About 10% of the daily dose is excreted in the urine. It is widely distributed throughout the body.
Clinical Use
Giardiasis
Prophylaxis of malaria
Tapeworm infections
Nebenwirkungen
Dizziness, headache and gastric problems are common. Toxic psychoses, bone marrow depression, yellow skin and exfoliative dermatitis are described. Poor toleration is noted, especially in children. It should not be used in combination with 8-aminoquinolines.
Synthese
Quinacrine, 6-chloro-9-(4-diethylamino-1-methylbutylamino)-2-methoxyacridine (37.1.4.3), is synthesized from 6,9-dichloro-2-methoxyacridine (37.1.4.2) and aforementioned 4-diethylamino-1-methylbutylamine (37.1.1.2). The 6,9-dichloro- 2-methoxyacridine (37.1.4.2) necessary for the synthesis is made in two stages. The initial reaction of 2,4-dichlorobenzoic acid and p-anizidine in the presence of copper dust and potassium carbonate gives 2-(4-methoxyanilino)-4-chlorobenzoic acid (37.1.4.1), which upon reaction with phosphorus oxychloride turns into the necessary 6,9-dichloro- 2-methoxyacridine (37.1.4.2).
läuterung methode
It crystallises from H2O (solubility is 2.8% at room temperature) as yellow crystals. It is slightly soluble in MeOH and EtOH. The free base crystallises from Me2CO or pet ether with m 86-88o, or aqueous EtOH with 85-87.5o. The bismethiodide has m 224o (from MeOH/EtOAc/Et3N), and the picrate has m 207-208o(dec) when crystallised from Me2CO/EtOH. It is an antimalarial, antiprotozoal and intercalates DNA. [Wolfe Antibiot 3 (Springer-Verlag) 203 1975, Beilstein 22 III/IV 6247, 22/12 V 235.]

Chinacrin-dihydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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