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Miconazol
MICONAZOLE BASE · Miconazol · 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]- (9CI) · r18134 · mjr1762 · R 18134 · Minostate · MICONAZOLE
Identifikatoren & physikalische Daten
| CAS No. | 22916-47-8 |
|---|---|
| Summenformel | C18H14Cl4N2O |
| Durchschnittliche Molmasse | 416,1 g/mol |
| Monoisotopische Masse | 413,986024 g/mol |
| SMILES | Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1 |
| InChIKey | BYBLEWFAAKGYCD-UHFFFAOYSA-N |
| PubChem CID | 4189 |
| ChEMBL | CHEMBL91 |
| ChEBI | CHEBI:82892 |
| EC No. | 245-324-5 |
| DTXSID | DTXSID6023319 |
| Lokaler Name | Miconazol |
Chemische & physikalische Eigenschaften
| XLogP | 5,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 27,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 417 |
| LogP (Verteilungskoeffizient) | 6.1 |
| Löslichkeit | 7.63e-04 g/LVery slightly soluble in water, freely soluble in methanol, soluble in ethanol (96 per cent).Freely soluble in alcohols or acetone. Also soluble in DMF or chloroform. Insoluble in water |
| Schmelzpunkt | 170159 - 163 °C159-163C |
| Physical Description | Solid |
| Kovats Retention Index | 298029622963.7 |
| Collision Cross Section | 187.51 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 555.1±50.0 °C(Predicted) |
| Dichte | 1.5326 (rough estimate) |
| Brechungsindex | 1.6200 (estimate) |
| Flammpunkt | 87°(189°F) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 6.91(H2O,t =25) (Uncertain) |
| Farbe | White to Off-White |
| Hauptanwendungen | pharmaceutical (small molecule) |
| InChI | 1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2 |
| InChIKey | BYBLEWFAAKGYCD-UHFFFAOYSA-N |
| SMILES | Clc1c(ccc(c1)Cl)C(OCc3c(cc(cc3)Cl)Cl)C[n]2cncc2 |
| CAS Datenbank | 22916-47-8(CAS DataBase Reference) |
| NIST chemische Informationen | Miconazole(22916-47-8) |
| EPA chemische Informationen | 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]- (22916-47-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1% (1 of 104) of reports.WarningH302 (98.1%): Harmful if swallowed [Warning Acute toxicity, oral]H400 (54.8%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (54.8%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]H413 (39.4%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 104 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 104 reports by companies.There are 10 notifications provided by 103 of 104 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Miconazole: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | IMAP assessments - 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-: Environment tier I assessmentIMAP assessments - 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-: Human health tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (98.1%)Aquatic Acute 1 (54.8%)Aquatic Chronic 1 (54.8%)Aquatic Chronic 4 (39.4%) |
| Expositionspfade | Topical |
| Toxizitätsübersicht | Miconazole interacts with 14-&alphademethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis. |
| Signs and Symptoms | Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)miconazoleDILI NegativeTopicalDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during LactationBecause miconazole has poor absorption from the skin and vagina and has poor oral bioavailability, it is unlikely to adversely affect the breastfed infant, including after topical application to the nipples. However, miconazole ointment appears to have no advantage over lanolin for treating sore nipples during breastfeeding and a survey of members of the Academy of Breastfeeding Medicine found topical miconazole is rarely prescribed to nursing mothers to treat thrush. Any excess cream or ointment should be removed from the nipples before nursing. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.◉ Effects in Breastfed InfantsRelevant published information was not found as of the revision date.◉ Effects on Lactation and BreastmilkIn a randomized, double-bind trial, lanolin was compared to an all-purpose nipple ointment containing mupirocin 1%, betamethasone 0.05%, and miconazole 2% for painful nipples while nursing in the first 2 weeks postpartum. The two treatments were equally effective in reducing nipple pain, nipple healing time, breastfeeding duration, breastfeeding exclusivity rate, mastitis and nipple symptoms, side effects or maternal satisfaction with treatment.◈ What is miconazole?Miconazole is a medication that has been used to treat fungal infections. As a cream, it has been used topically (on the skin) to treat skin infections and as a cream or suppository (inserted into the vagina) to treat vaginal infections. Some brand names for miconazole are Desenex®, Lomitrin AF®, Monistat®, Micatin® and Mitrazole®.Sometimes when women find out they are pregnant, they think about changing how they take their medication, or stopping their medication altogether. However, it is important to talk with your healthcare providers before making any changes to how you take your medication. Your healthcare providers can talk with you about the benefits of treating your condition and the risks of untreated illness during pregnancy.◈ What should I do if I think I have a vaginal yeast infection while pregnant?Women are more likely to get yeast infections during pregnancy than at other times. If you think you have a vaginal yeast infection, it is important to see your healthcare provider to be sure the infection is yeast before trying to treat it on your own. If you have another type of infection, you may need different treatment.◈ I use miconazole. Can it make it harder for me to get pregnant?Using miconazole is not expected to make it harder to get pregnant.◈ Does using miconazole increase the chance of miscarriage?Miscarriage is common and can occur in any pregnancy for many different reasons. One study found a small increased chance for miscarriage with the use of miconazole, but there were several problems with this study that could have affected the results. Other studies have not found that miconazole increases the chance of miscarriage.◈ Does taking miconazole increase the chance of birth defects?Birth defects can happen in any pregnancy for different reasons. Out of all babies born each year, about 3 out of 100 (3%) will have a birth defect. We look at research studies to try to understand if an exposure, like miconazole, might increase the chance of birth defects in a pregnancy.Topical or vaginal medications enter the body in lower amounts than oral (pill) medications. This means less medication reaches the developing fetus. Since topical and vaginal miconazole are not well absorbed, they are unlikely to increase risks to a pregnancy. Most studies have shown that miconazole at low doses (◈ Does using miconazole increase the chance of other pregnancy-related problems?Studies have not been done to see if miconazole increases the chance for pregnancy-related problems such as preterm delivery (birth before week 37) or low birth weight (weighing less than 5 pounds, 8 ounces [2500 grams] at birth).◈ Does using miconazole in pregnancy affect future behavior or learning for the child?Studies have not been done to see if miconazole can cause behavior or learning issues for the child.◈ Breastfeeding while using miconazole:There are no studies looking at the use of miconazole use during breastfeeding. However, because only small amounts of the medication are expected to pass into breastmilk when miconazole is used topically or vaginally, it is not expected to cause side effects in a nursing child. Miconazole cream has been used directly on infants under the care of a healthcare provider to treat fungal infections. If used on the nipples, any excess cream or ointment should be removed from the nipples before nursing. Be sure to talk to your healthcare provider about all your breastfeeding questions.◈ If a man uses miconazole, could it affect his fertility or increase the chance of birth defects?Studies have not been done to see if miconazole could affect male fertility (ability to get a woman pregnant) or increase the chance of birth defects above the background risk. In general, exposures that fathers or sperm donors have are unlikely to increase risks to a pregnancy. For more information, please see the MotherToBaby fact sheet Paternal Exposures at https://mothertobaby.org/fact-sheets/paternal-exposures-pregnancy/. |
| Toxicity Data | LD50: 3800 mg/kg (Oral, Mouse) (A308) LD50: 3 gm/kg (Oral, Rat) (A308) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 3249 |
| Zollcode | 2933290000 |
| R-Sätze (R) | 22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-36 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralAquatic Chronic 4 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Antifungal;Sterol 14-demethylase inhibitor. Miconazole (Monistat-Derm, Micatin, etc.) is a synthetic imidazole antifungal compound that acts by altering cell membrane permeability. It is effective against most dermatophyte species, P. orbiculare, and C. albicans.