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Oxiconazole nitrate

Names

[ CAS No. ]:
64211-46-7

[ Name ]:
Oxiconazole nitrate

[Synonym ]:
Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-, O-(2,4-dichlorophenyl)oxime, (1Z)-, nitrate (1:1)
MFCD00865580
Oxiconazole nitrate
(1Z)-N-(2,4-Dichlorophenoxy)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanimine nitrate (1:1)
EINECS 264-730-3
(z)-1-(2-(2,4-dichlorophenyl)-2-(((2,4-dichlorophenyl)oxy)imino)ethyl)-1h-IMIDAZOLE mononitrate

Biological Activity

[Description]:

Oxiconazole nitrate is a broad spectrum antifungal which can inhibit the growth of T. tonsurans and T. rubrum with MIC90s of 0.25 and 0.5 μg/mL, respectively.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal
Research Areas >> Infection

[Target]

MIC90: 0.25 μg/mL (T. tonsurans), 0.5 μg/mL (T. rubrum)[1]


[In Vitro]

Oxiconazole nitrate is the more active compound in tests with T. tonsurans and T. rubrum. Twelve isolates are inhibited by 0.063 μg/mL of oxiconazole; corresponding econazole MICs range from 0.063 (three isolates) to 8 (two isolates) μg/mL. Three isolates have oxiconazole MICs of 16 or 32 μg/mL[1].

[In Vivo]

The baseline distortion product otoacoustic emission (DPOAE) results of the right ears of all animals tested are normal. Animals in groups I, II, IV and V show no statistically significant change in the DPOAE amplitudes. The rats in the gentamicingroup show a significant decrease[2].

[Cell Assay]

A total of 121 isolates of pathogenic fungi are tested. The three drugs (including Oxiconazole nitrate) are serially diluted in sterile saline. For each test plate, 2 mL of a solution of drug in sterile saline is added to an 18 mL blank of molten agar medium at 50°C and mixed well; the resulting mixtures are then poured into the plates and allowed to solidify. The resulting drug dilution sequences range from 128 to 0.063 μg/mL. Control plates are prepared in a similar manner using 2 mL blanks of sterile saline. The plates are then inoculated using a replicator. Incubation is at 30°C for a minimum of 96 hr. The Minimal Inhibitory Concentration (MIC) is defined as the lowest concentration of drug producing complete inhibition of growth[1].

[Animal admin]

Fifty adult rats are divided into 5 groups consisting of 10 animals each. Over 14 days, the rats in group I receive 0.1 mL of Oxiconazole nitrate-containing solution drops, group II receives 4% boric acid solution in alcohol drops, and groups III and IV receive gentamicin (40 mg/mL) and saline solutions, respectively. Group V receives no medication. Each solution used is given twice a day[2].

[References]

[1]. Shadomy S, et al. Further in vitro studies with oxiconazole nitrate. Diagn Microbiol Infect Dis. 1988 Apr;9(4):231-7.

[2]. Özdemir S, et al. Effects of topical oxiconazole and boric acid in alcohol solutions to rat inner ears. Otolaryngol Head Neck Surg. 2013 Jun;148(6):1023-7.


[Related Small Molecules]

Cycloheximide | Hygromycin B | Cancidas | 5-Flucytosine | Posaconazole | Terbinafine | Ciclopirox | Isavuconazole | Anidulafungin | Clotrimazole | Clioquinol | Miconazole Nitrate | Pimaricin | Ascomycin | Econazole (nitrate)

Chemical & Physical Properties

[ Boiling Point ]:
576.8ºC

[ Melting Point ]:
137-1380C

[ Molecular Formula ]:
C18H14Cl4N4O4

[ Molecular Weight ]:
492.14

[ Flash Point ]:
302.6ºC

[ PSA ]:
105.46000

[ LogP ]:
6.15550

[ Storage condition ]:
Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KM5771000
CHEMICAL NAME :
Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-, o-((2,4-dichlorophenyl)methyl)oxime, nitrate, (Z)-
CAS REGISTRY NUMBER :
64211-46-7
LAST UPDATED :
199603
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C18-H13-Cl4-N3-O.H-N-O3
MOLECULAR WEIGHT :
492.16

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2458 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 37,1355,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
630 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 17,365,1986
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>7500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,227,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2630 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 17,365,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
595 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 17,365,1986
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>15 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,227,1990

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
37/39-26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
CQ7700000

[ HS Code ]:
29335995

Customs

[ HS Code ]: 29335995


Related Compounds