Naftifine hydrochloride

Bezeichnung:Naftifine hydrochloride

CAS-Nr65473-14-5

Englisch Name:Naftifine hydrochloride

CBNumberCB6349312

SummenformelC21H22ClN

Molgewicht323.86

MOL-Datei65473-14-5.mol

Naftifine hydrochloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	172-175°C
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	ethanol: soluble50mg/mL
Aggregatzustand	Solid
Farbe	White to Off-White
Merck	14,6355
InChI	InChI=1S/C21H21N.ClH/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20;/h2-15H,16-17H2,1H3;1H/b11-8+;
InChIKey	OLUNPKFOFGZHRT-YGCVIUNWSA-N
SMILES	N(C/C=C/C1=CC=CC=C1)(C)CC1=C2C(C=CC=C2)=CC=C1.[H]Cl
CAS Datenbank	65473-14-5(CAS DataBase Reference)

Sicherheit

S-Sätze:	24/25
WGK Germany	nwg
RTECS-Nr.	QJ8650000
HS Code	29214990

Gefahreninformationscode (GHS)

Naftifine hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Naftifine hydrochloride is a topical antifungal agent which acts via inhibiting squalene epoxidase. It demonstrates good activity against Trichophyton, Epidermophyton, Microsporum, Aspergillus, and species. It is the prototype of a significantly improved series of antifungal agents, exemplified by SF 86-327 in which the phenyl group of naftifine has been replaced by t-butylace tylene.
Chemische Eigenschaften
White Powder
Originator
Sandoz (Switzerland)
Verwenden
Antimycotic allylamine. An antifungal (topical) agent.
Verwenden
An antifungal agent
Definition
ChEBI: Naftifine hydrochloride is a hydrochloride and an allylamine antifungal drug.
Trademarks
Naftin (Merz);EXODERIL.
Allgemeine Beschreibung
N-Methyl-N-(3-phenyl2-propenyl)-1-naphthalenemethanaminehydrochloride (Naftin) is a white crystallinepowder that is soluble in polar solvents such asethanol and methylene chloride. It is supplied in a 1% concentrationin a cream and in a gel for the topical treatmentof ringworm, athlete’s foot, and jock itch. Although unapprovedfor these uses, naftifine has shown efficacy fortreatment of ringworm of the beard, ringworm of the scalp,and tinea versicolor.
Clinical Use
Naftifine hydrochloride (Naftin) is available for topical use only in the treatment of cutaneous dermatophyte and Candida infections; it is as effective as topical azoles for these conditions.
Synthese
Naftifine hydrochloride is prepared by the reaction of (E)-N-methylcinnamylamine and 1-Chloromethylnaphthalene. The steps are as follows:
Step 1: (E)-N-methylcinnamylamine; 1-Chloromethylnaphthalene With sodium hydroxide In toluene at 86℃; for 6h;
Step 2: With hydrogenchloride In water; toluene at 15 - 20℃; for 3.5h；
Step 3: Add toluene (75 mL) to the yellow oil of step 2 (trans-N-cinnamomethylamine crude)And 15% NaOH (9.8g),Warming up,Stir well,When the temperature rises to 86 ° C,1-Chloromethylnaphthalene (11.8 g,100.2mmol), dripping,The reaction was incubated at 86 ° C for 6 h.Medium controlled N-cinnamylmethylamine is less than 0.5%,Cool down to 30 ° C, add water (75mL) to the system,Stirring and standing, separating the organic phase,The organic phase was washed with water (75 mL).Allow to stand and separate the organic phase, Concentrated hydrochloric acid (7.0 g) was added to the organic phase in a 15 ° C ice water bath.Adjust the pH to about 2 and stir for 0.5 h.After stirring at 20 ° C for 3 h, the filter cake was filtered.The filter cake was rinsed with toluene (20 mL).Obtained a wet cake (reduced naftifine hydrochloride) 19.5g;The wet crude product obtained in step 3 (crude naftifine hydrochloride) was added to isopropyl alcohol (38.6 g).Warmed to 85 ° C, dissolved,Slowly cool after dissolving,The cooling rate is 10 °C / h,A small amount of solid precipitated at 35 ° C.Crystallization at this temperature for 2 h,Continue to cool down to 20 ° C,Insulation for 3h,filter,Get the wet cake,The filter cake was dried under vacuum at 45 ° C.Obtained 16.2g of finished naftifine hydrochloride,The purity of the finished naftifine hydrochloride was 99.4% (HPLC normalization method).The product yield was 68.0%.The product yield is the molar yield,The calculation is as follows:Product yield (%)={m/[(m0/M0)*M]}*100%Symbol Description: m is the mass of the finished product, g; m0 is the mass of cinnamyl alcohol, g; M is the molar mass of naftifine hydrochloride,g/mol; M0 is the molar mass of cinnamyl alcohol, g/mol.

Naftifine hydrochloride Upstream-Materialien And Downstream Produkte

Naftifine hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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