Miconazole

Names

[ Name ]:
Miconazole

[Synonym ]:
1-[2-(2,4-Dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole
EINECS 245-324-5
1-[2,4-Dichloro-b-[(2,4-dichlorobenzyl)oxy]phenethyl]imidazole
Daktarin IV
MFCD00216019
MONISTAT IV
Minostate
1-(2,4-dichloro-β-((2,4-dichlorobenzyl)oxy)phenethyl) imidazole
1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-
Desenex
Miconozole
(±)-Miconazole
Monistat
mjr1762
1-[2-(2,4-dichlorophenyl)-2-{[(2,4-dichlorophenyl)methyl]oxy}ethyl]-1H-imidazole
1-{2-[(2,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
micronazol
1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-
Miconazole
Zeasorb-AF

Biological Activity

[Description]:

Miconazole (Monistat) is an imidazole antifungal agent.Target: AntifungalMiconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucous membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. It can also be used against certain species of Leishmania protozoa which are a type of unicellular parasite that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some antibacterial properties. Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process. From Wikipedia.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[References]

[1]. http://en.wikipedia.org/wiki/Miconazole

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
555.1±50.0 °C at 760 mmHg

[ Melting Point ]:
159-163ºC

[ Molecular Formula ]:
C₁₈H₁₄Cl₄N₂O

[ Molecular Weight ]:
416.129

[ Flash Point ]:
289.5±30.1 °C

[ Exact Mass ]:
413.986023

[ PSA ]:
27.05000

[ LogP ]:
5.93

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.625

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI4770000

CHEMICAL NAME :: Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)pheneth yl)-

CAS REGISTRY NUMBER :: 22916-47-8

BEILSTEIN REFERENCE NO. :: 0965511

LAST UPDATED :: 199806

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C18-H14-Cl4-N2-O

MOLECULAR WEIGHT :: 416.14

WISWESSER LINE NOTATION :: T5N CNJ A1YR BG DG&O1R BG DG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - infant

DOSE/DURATION :: 104 mg/kg/4D-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 349 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 105 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 519 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 220 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90570 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Cardiac - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Cardiac - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 800 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3100 mg/kg

SEX/DURATION :: female 1-31 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Mold - Aspergillus nidulans

DOSE/DURATION :: 4160 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 79,169,1980 *** REVIEWS *** TOXICOLOGY REVIEW PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,333,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4278 No. of Facilities: 46 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 8954 (estimated) No. of Female Employees: 7689 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H413

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
22-36

[ RIDADR ]:
UN 3249

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933290090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Simultaneous determination of seven azole antifungal drugs in serum by ultra-high pressure liquid chromatography and diode array detection.

Acta Clin. Belg. 69(1) , 53-61, (2014)

Azole antifungals are a group of fungistatic agents that can be administered orally or parenterally. The determination of the concentrations of these antifungals (miconazole, fluconazole, ketoconazole...

A comparison of in vitro ADME properties and pharmacokinetics of azithromycin and selected 15-membered ring macrolides in rodents.

Eur. J. Drug Metab. Pharmacokinet. 39(4) , 263-76, (2014)

The purpose of this study was to evaluate the impact of structural modifications on the 15-membered macrolactone ring and/or substituents on the in vitro ADME properties and in vivo pharmacokinetic (P...

HPLC and chemometric methods for the simultaneous determination of miconazole nitrate and nystatin.

J. Chromatogr. Sci. 50(10) , 855-61, (2012)

High-performance liquid chromatography (HPLC) and chemometric methods were applied to the simultaneous determination of the two nonsteroidal antifungal drugs, miconazole (MIC) and nystatin (NYS). The ...