Clotrimazol

Bezeichnung:Clotrimazol

CAS-Nr23593-75-1

Englisch Name:Clotrimazole

CBNumberCB7404063

SummenformelC22H17ClN2

Molgewicht344.84

MOL-Datei23593-75-1.mol

Synonyma

Clotrimazol

Clotrimazol physikalisch-chemischer Eigenschaften

Schmelzpunkt	147-149°C
Siedepunkt	501.14°C (rough estimate)
Dichte	1.1095 (rough estimate)
Brechungsindex	1.5940 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in chloroform, DMSO, DMF and alcohols
pka	pKa 4.7(EtOH 50%aq ) (Uncertain)
Farbe	White to Almost white
Wasserlöslichkeit	<10mg/L(25 ºC)
maximale Wellenlänge (λmax)	556nm(Phosphate buffer sol.)(lit.)
Merck	14,2417
InChI	InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
InChIKey	VNFPBHJOKIVQEB-UHFFFAOYSA-N
SMILES	C1N(C(C2=CC=CC=C2Cl)(C2=CC=CC=C2)C2=CC=CC=C2)C=CN=1
NIST chemische Informationen	Clotrimazole(23593-75-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	NI4377000
HS Code	29332900
Giftige Stoffe Daten	23593-75-1(Hazardous Substances Data)
Toxizität	LD50 in male mice, rats (mg/kg): 923, 708 orally (Tettenborn)

Gefahreninformationscode (GHS)

Clotrimazole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Clotrimazole is an imidazole antifungal that is active against a wide variety of fungal forms and is effective in many types of fungal infections. It tightly binds sterol 14-α demethylase isoform B from A. fumigatus (K_D = 103 nM) and, like other imidazoles, disturbs the fungal cell membrane. In mammalian cells, clotrimazole potently inhibits the calcium-dependent potassium channels K_v1.3 and IK-1 (IC₅₀ = 6.0 and 0.07 μM, respectively).
Chemische Eigenschaften
White or pale yellow, crystalline powder.
Originator
Canesten,Bayer,UK,1973
Verwenden
Clotrimazole formally also is an imidazole derivative because of the presence of an imidazole ring in its structure. It is believed that, like miconazole, econazole, and other “pure” representatives of the imidazole class, it also inhibits the biosynthesis of ergosterin in the cytoplasmatic membrane of fungi.
In terms of pharmacological action, clotrimazole is very similar to miconazole. It has a broad spectrum of antifungal activity. It is effective with respect to dermatophytes, and it also has an antimicrobial effect against streptococci and staphylococci. It is also effective with respect to trichomonases. It is very widely used, both externally and vaginally for treating superficial infections. Synonyms of this drug are canesten, empecid, lotrimin, micosporin, and others.
Verwenden
An antifungal compound and CYP inhibitor.
Clotrimazole (Lotrimin, Mycelex, etc.) is a synthetic imidazole agent. It acts by altering cell membrane permeability. It inhibits the growth of most dermatophyte species, yeast and Malassezia furfur.
Verwenden
Clotrimazole is an antifungal agent.
Indications
Clotrimazole (Lotrimin, Gyne-Lotrimin, Mycelex) is a broad-spectrum fungistatic imidazole drug used in the topical treatment of oral, skin, and vaginal infections with C. albicans. It is also employed in the treatment of infections with cutaneous dermatophytes.
Topical use results in therapeutic drug concentrations in the epidermis and mucous membranes; less than 10% of the drug is systemically absorbed. Although clotrimazole is generally well tolerated, local abdominal cramping, increased urination, and transient liver enzyme elevations have been reported.
Definition
ChEBI: A member of the class of imidazoles that is 1H-imidazole in which the hydrogen attached to a nitrogen is replaced by a monochlorotrityl group.
Manufacturing Process
156.5 g (0.5 mol) o-chlorophenyldiphenylmethyl chloride and 34 g (0.5 mol) imidazole are dissolved in 500 ml acetonitrile, with stirring, and 51 g (0.5 mol) triethylamine are added, whereupon separation of triethylamine hydrochloride occurs even at room temperature. In order to complete the reaction, heating at 50°C is carried out for 3 hours. After cooling, one liter of benzene is added and the reaction mixture is stirred, then washed salt-free with water. The benzene solution is dried over anhydrous sodium sulfate, filtered and concentrated by evaporation; giving 167 g crude 1-(ochlorophenylbisphenylmethyl)-imidazole. By recrystallization from acetone, 115 g (= 71% of the theory) of pure 1-(o-chlorophenylbisphenylmethyl)- imidazole of MP 154° to 156°C are obtained.
Trademarks
Gyne- Lotrimin (Schering-Plough); Gynix (Teva); Lotrimin (Schering-Plough); Mycelex (Bayer).
Therapeutic Function
Antifungal
Allgemeine Beschreibung
Chemical structure: imidazole
Biochem/physiol Actions
Clotrimazole is a specific inhibitor of Ca2+-activated K+ channels. It is an antifungal azole. Clotrimazole is a derivative of imidazole and has similar antimicrobial action and activity to ketoconazole. It inhibits cytochrome P450-dependent 14α-demethylase, which is critical to ergosterol biosynthesis. The accumulated 14α-methylated sterols change the membrane structure of sensitive fungi, altering cell membrane permeability.
Clinical Use
1-(o-Chloro-α,α-diphenylbenzyl)imidazole (Lotrimin, Gyne-Lotrimin, Mycelex) is a broad-spectrum antifungal drug thatis used topically for the treatment of tinea infections and candidiasis.It occurs as a white crystalline solid that is sparinglysoluble in water but soluble in alcohol and most organic solvents.It is a weak base that can be solubilized by dilute mineralacids.
Clotrimazole is available as a solution in polyethyleneglycol 400, a lotion, and a cream in a concentration of 1%.These are all indicated for the treatment of tinea pedis, tineacruris, tinea capitis, tinea versicolor, or cutaneous candidiasis.A 1% vaginal cream and tablets of 100 mg and 500 mgare available for vulvovaginal candidiasis. Clotrimazole isextremely stable, with a shelf life of more than 5 years.
Synthese
Clotrimazole, 1-(o-chloro-α,α-diphenylbenzyl)imidazole (35.2.21), is synthesized by reacting 2-chlorotriphenylmethylchloride (35.2.20) with imidazole in the presence of triethylamine.

The starting substance 2-chlorotriphenylmethylchloride is made in various ways. In particular, chlorinating 2-chlorotoluene under light makes 2-chlorotrichloromethylbenzene (35.2.22), which is reacted with benzene in the presence of aluminum chloride to give 2-chlorotriphenylmethylchloride (35.2.20).

An alternative way of making 2-chlorotriphenylmethylchloride is a Grignard reaction between 2-chlorobenzolphenone and phenylmagnesium bromide, followed by substitution of the hydroxyl group in the resulting 2-chlorotriphenylmethylcarbinol (35.2.23) with a chlorine using thionyl chloride.

And finally, reacting phosphorous pentachloride with 2-chlorobenzophenone gives 2- chloro-1,1-dichlorodiphenylmethane (35.2.24), which is used for the alkylation of benzene in the presence of aluminum chloride and gives 2-chlorotriphenylmethylchloride (35.2.20).
Veterinary Drugs and Treatments
Topical clotrimazole has activity against dermatophytes and yeasts; it may be useful for localized lesions associated with Malassezia. It is not very effective in treating dermatophytosis in cats.
Clotrimazole inhibits the biosynthesis of ergosterol, a component of fungal cell membranes leading to increased membrane permeability and probable disruption of membrane enzyme systems.
Lager
Store at RT

Clotrimazole Upstream-Materialien And Downstream Produkte

Clotrimazol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

23593-75-1, Clotrimazole Verwandte Suche:

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