Synonym
Miconazole, Desenex, Monistat, Zeasorb-AF, Brentan, Dactarin, R-14,889
IUPAC/Chemical Name
1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole
InChi Key
BYBLEWFAAKGYCD-UHFFFAOYSA-N
InChi Code
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
SMILES Code
ClC1=CC=C(COC(C2=CC=C(Cl)C=C2Cl)CN3C=CN=C3)C(Cl)=C1
Appearance
White to off-white crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Miconazole (R18134) is an imidazole antifungal agent.
In vitro activity:
Miconazole was found efficacious against gram-positive aerobic bacteria (n=62 species), the MICs against Staphylococcus (S.) aureus, S. spp., Streptococcus spp. und Enterococcus spp. ranged between 0.78 and 6.25 μg/mL. In conclusion, for the gram-positive aerobic bacteria the MICs of miconazole were found within a range which is much lower than the concentration of miconazole used in topical preparations (2%). Thus topically applied miconazole might be a therapeutic option in skin infections especially caused by gram-positive bacteria even by those strains which are resistant to antibiotics.
Reference: Mycoses. 2017 Aug;60(8):552-557. https://pubmed.ncbi.nlm.nih.gov/28370366/
In vivo activity:
The cooperative ability was significantly improved in APP/PS1 mice treated with miconazole. Miconazole treatment increased oligodendrocyte maturation and myelin sheath thickness without reducing Aβ plaque deposition, reactive gliosis, and inflammatory factor levels in the mPFC. Miconazole also protected cultured oligodendrocytes from the toxicity of Aβ1-42.
Reference: Int J Neuropsychopharmacol. 2022 Nov 17;25(11):951-967. https://pubmed.ncbi.nlm.nih.gov/36112386/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
91.5 |
219.88 |
|
| Ethanol |
83.0 |
199.46 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
416.13
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Gong L, Zhu T, Chen C, Xia N, Yao Y, Ding J, Xu P, Li S, Sun Z, Dong X, Shen W, Sun P, Zeng L, Xie Y, Jiang P. Miconazole exerts disease-modifying effects during epilepsy by suppressing neuroinflammation via NF-κB pathway and iNOS production. Neurobiol Dis. 2022 Oct 1;172:105823. doi: 10.1016/j.nbd.2022.105823. Epub 2022 Jul 22. PMID: 35878745.
2. Nenoff P, Koch D, Krüger C, Drechsel C, Mayser P. New insights on the antibacterial efficacy of miconazole in vitro. Mycoses. 2017 Aug;60(8):552-557. doi: 10.1111/myc.12620. Epub 2017 Mar 30. PMID: 28370366.
3. Wang Z, Zhang Y, Feng W, Pang Y, Chen S, Ding S, Chen Y, Sheng C, Marshall C, Shi J, Xiao M. Miconazole Promotes Cooperative Ability of a Mouse Model of Alzheimer Disease. Int J Neuropsychopharmacol. 2022 Nov 17;25(11):951-967. doi: 10.1093/ijnp/pyac061. PMID: 36112386; PMCID: PMC9670758.
4. Alsharif IA, Fayed HM, Abdel-Rahman RF, Abd-Elsalam RM, Ogaly HA. Miconazole Mitigates Acetic Acid-Induced Experimental Colitis in Rats: Insight into Inflammation, Oxidative Stress and Keap1/Nrf-2 Signaling Crosstalk. Biology (Basel). 2022 Feb 13;11(2):303. doi: 10.3390/biology11020303. PMID: 35205169; PMCID: PMC8869207.
In vitro protocol:
1. Gong L, Zhu T, Chen C, Xia N, Yao Y, Ding J, Xu P, Li S, Sun Z, Dong X, Shen W, Sun P, Zeng L, Xie Y, Jiang P. Miconazole exerts disease-modifying effects during epilepsy by suppressing neuroinflammation via NF-κB pathway and iNOS production. Neurobiol Dis. 2022 Oct 1;172:105823. doi: 10.1016/j.nbd.2022.105823. Epub 2022 Jul 22. PMID: 35878745.
2. Nenoff P, Koch D, Krüger C, Drechsel C, Mayser P. New insights on the antibacterial efficacy of miconazole in vitro. Mycoses. 2017 Aug;60(8):552-557. doi: 10.1111/myc.12620. Epub 2017 Mar 30. PMID: 28370366.
In vivo protocol:
1. Wang Z, Zhang Y, Feng W, Pang Y, Chen S, Ding S, Chen Y, Sheng C, Marshall C, Shi J, Xiao M. Miconazole Promotes Cooperative Ability of a Mouse Model of Alzheimer Disease. Int J Neuropsychopharmacol. 2022 Nov 17;25(11):951-967. doi: 10.1093/ijnp/pyac061. PMID: 36112386; PMCID: PMC9670758.
2. Alsharif IA, Fayed HM, Abdel-Rahman RF, Abd-Elsalam RM, Ogaly HA. Miconazole Mitigates Acetic Acid-Induced Experimental Colitis in Rats: Insight into Inflammation, Oxidative Stress and Keap1/Nrf-2 Signaling Crosstalk. Biology (Basel). 2022 Feb 13;11(2):303. doi: 10.3390/biology11020303. PMID: 35205169; PMCID: PMC8869207.
1: Zhang LW, Fu JY, Hua H, Yan ZM. Efficacy and safety of miconazole for oral candidiasis: a systematic review and meta-analysis. Oral Dis. 2016 Apr;22(3):185-95. doi: 10.1111/odi.12380. Epub 2015 Dec 4. Review. PubMed PMID: 26456226.
2: Piérard GE, Hermanns-Lê T, Delvenne P, Piérard-Franchimont C. Miconazole, a pharmacological barrier to skin fungal infections. Expert Opin Pharmacother. 2012 Jun;13(8):1187-94. doi: 10.1517/14656566.2012.687047. Epub 2012 May 8. Review. PubMed PMID: 22568580.
3: Vazquez JA, Sobel JD. Miconazole mucoadhesive tablets: a novel delivery system. Clin Infect Dis. 2012 May;54(10):1480-4. doi: 10.1093/cid/cis205. Epub 2012 Apr 10. Review. PubMed PMID: 22495075.
4: Miki A, Ohtani H, Sawada Y. Warfarin and miconazole oral gel interactions: analysis and therapy recommendations based on clinical data and a pharmacokinetic model. J Clin Pharm Ther. 2011 Dec;36(6):642-50. doi: 10.1111/j.1365-2710.2010.01229.x. Epub 2010 Dec 8. Review. PubMed PMID: 21143257.
5: Quatresooz P, Vroome V, Borgers M, Cauwenbergh G, Piérard GE. Novelties in the multifaceted miconazole effects on skin disorders. Expert Opin Pharmacother. 2008 Aug;9(11):1927-34. doi: 10.1517/14656566.9.11.1927 . Review. PubMed PMID: 18627330.
6: Ben Slama L, Hasni W. [Miconazole in gingival muco-adhesive tablet (Loramyc 50mg)]. Rev Stomatol Chir Maxillofac. 2008 Jun;109(3):197-200. doi: 10.1016/j.stomax.2008.04.006. Epub 2008 Jun 6. Review. French. PubMed PMID: 18538809.
7: Mazneĭkova V. [Vaginal candidiasis--treatment protocols using miconazole and fluconazole]. Akush Ginekol (Sofiia). 2003;42 Suppl 2:30-4. Review. Bulgarian. PubMed PMID: 14619753.
8: Marinová I, Szabadosová V, Brandeburová O, Krcméry V Jr. Rhodotorula spp. fungemia in an immunocompromised boy after neurosurgery successfully treated with miconazole and 5-flucytosine: case report and review of the literature. Chemotherapy. 1994 Jul-Aug;40(4):287-9. Review. PubMed PMID: 8082417.
9: Horton CM, Freeman CD, Nolan PE Jr, Copeland JG 3rd. Cyclosporine interactions with miconazole and other azole-antimycotics: a case report and review of the literature. J Heart Lung Transplant. 1992 Nov-Dec;11(6):1127-32. Review. PubMed PMID: 1457436.
10: Heel RC, Brogden RN, Pakes GE, Speight TM, Avery GS. Miconazole: a preliminary review of its therapeutic efficacy in systemic fungal infections. Drugs. 1980 Jan;19(1):7-30. Review. PubMed PMID: 6988200.
