O-Desulfo Micafungin
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| Category | Antifungal |
| Catalog number | BBF-05832 |
| CAS | 539823-80-8 |
| Molecular Weight | 1190.23 |
| Molecular Formula | C56H71N9O20 |
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Description
O-Desulfo Micafungin is an impurity of caspofungin or micafungin. Micafungin is a polyene antifungal medication used to treat and prevent invasive fungal infections including candidemia, abscesses and esophageal candidiasis.
Specification
| Synonyms | Micafungin (m1); Pneumocandin A0, 1-((4R,5R)-4,5-dihydroxy-N2-(4-(5-(4-(pentyloxy)phenyl)-3-isoxazolyl)benzoyl)-L-ornithine)-4-((4S)-4-(3,4-dihydroxyphenyl)-4-hydroxy-L-threonine)-; 1-((4R,5R)-4,5-Dihydroxy-N2-(4-(5-(4-(pentyloxy)phenyl)-3-isoxazolyl)benzoyl)-L-ornithine)-4-((4S)-4-(3,4-dihydroxyphenyl)-4-hydroxy-L-threonine)pneumocandin A0 |
| IUPAC Name | N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-2-(3,4-dihydroxyphenyl)-1,2-dihydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzamide |
| Canonical SMILES | CCCCCOC1=CC=C(C=C1)C2=CC(=NO2)C3=CC=C(C=C3)C(=O)NC4CC(C(NC(=O)C5C(C(CN5C(=O)C(NC(=O)C(NC(=O)C6CC(CN6C(=O)C(NC4=O)C(C)O)O)C(C(C7=CC(=C(C=C7)O)O)O)O)C(CC(=O)N)O)C)O)O)O |
| InChI | InChI=1S/C56H71N9O20/c1-4-5-6-17-84-32-14-11-28(12-15-32)40-21-33(63-85-40)27-7-9-29(10-8-27)49(76)58-34-20-39(71)52(79)62-54(81)45-46(73)25(2)23-65(45)56(83)43(38(70)22-41(57)72)60-53(80)44(48(75)47(74)30-13-16-36(68)37(69)18-30)61-51(78)35-19-31(67)24-64(35)55(82)42(26(3)66)59-50(34)77/h7-16,18,21,25-26,31,34-35,38-39,42-48,52,66-71,73-75,79H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,72)(H,58,76)(H,59,77)(H,60,80)(H,61,78)(H,62,81)/t25-,26+,31+,34-,35-,38+,39+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1 |
| InChI Key | VJHYOZWFHJBKMZ-CICALKLBSA-N |
Properties
| Boiling Point | 1600.0±65.0°C at 760 mmHg |
| Density | 1.56±0.1 g/cm3 |
Reference Reading
1. An overview of micafungin as a treatment option for invasive candidiasis in pediatric patients younger than 4 months old
Matteo Bassetti, Daniele Roberto Giacobbe, Antonio Vena, Susanna Esposito Expert Opin Pharmacother. 2022 Dec;23(18):1987-1993. doi: 10.1080/14656566.2022.2147824. Epub 2022 Nov 22.
Introduction: Invasive candidiasis remains a leading cause of morbidity and mortality in various categories of patients at risk. Areas covered: Structure and mechanism of action, pharmacokinetics and pharmacodynamics, clinical studies, safety, and regulatory status of micafungin are explored in the present review, focusing on pediatric patients younger than 4 months old. Expert opinion: Although limited, the available data on the efficacy and safety of micafungin in pediatric patients younger than 4 months old support its use for the treatment of invasive candidiasis in this particular population, in line with the most updated recommendations from the European Medicines Agency and the US Food and Drug Administration. Additional study, especially of high-dose micafungin, could further optimize the use of this drug in pediatric patients younger than 4 months old with Candida meningoencephalitis. The recent worrisome worldwide diffusion of Candida auris, more frequently resistant to polyenes than to echinocandins and showing high rates of resistance to azoles, could render micafungin even more crucial for guaranteeing an efficacious antifungal treatment for invasive candidiasis in pediatric patients younger than 4 months old.
2. Micafungin injection for the treatment of invasive candidiasis in pediatric patients under 4 months of age
Nahed Abdel-Haq, Stephanie M Smith, Basim I Asmar Expert Rev Anti Infect Ther. 2022 Apr;20(4):493-505. doi: 10.1080/14787210.2022.2013807. Epub 2021 Dec 20.
Introduction: Neonates and young infants with invasive candidiasis are particularly at increased risk of dissemination including hematogenous Candida meningoencephalitis. The echinocandins including micafungin have emerged as a preferred agent in most cases of candidemia and invasive candidiasis but data in pediatric patients under 4 months of age are limited. Areas covered: In this report, we review the micafungin use in infants younger than 4 months of age. Animal studies as well as clinical data that support its use in neonatal candidiasis are reviewed. In addition, the status of FDA approval and the rationale of micafungin dosing recommendations in infants<4 months are discussed. Expert opinion: A dose of 4 mg/kg was approved for treatment of candidemia, Candida peritonitis and abscesses excluding meningoencephalitis or ocular involvement in patients younger than 4 months of age. However, because of the risk of central nervous system dissemination as well as the difficulty in establishing this diagnosis, this dose is inadequate to treat ill infants with candidemia. More studies are needed to establish the safety and efficacy of micafungin daily dose of at least 10 mg/kg in infants younger than 4 months of age when hematogenous Candida meningoencephalitis or ocular involvement cannot be excluded.
3. Fungi-derived lipopeptide antibiotics developed since 2000
Pengchao Zhao, Yun Xue, Xin Li, Jinghua Li, Zhanqin Zhao, Chunshan Quan, Weina Gao, Xiangyang Zu, Xuefei Bai, Shuxiao Feng Peptides. 2019 Mar;113:52-65. doi: 10.1016/j.peptides.2019.02.002. Epub 2019 Feb 7.
Lipopeptide antibiotics have linear or cyclic structures with one or more hydrocarbon tails linked to the N-terminus of a short oligopeptide that may be chemically modified and/or contain unusual amino acid residues in their structures. They possess huge potential as pharmaceutical drugs and biocontrol agents, and ˜30 representative genera of fungi are known to produce them. Some chemically synthesised derivatives have already been developed into commercial products or subjected to clinical trials, including cilofungin, caspofungin, micafungin, anidulafungin, rezafungin, emodepside, fusafungine and destruxins. This review summarizes 200 fungi-derived compounds reported since 2000, including 95 cyclic depsipeptides, 67 peptaibiotics (including 35 peptaibols, eight lipoaminopeptides, and five lipopeptaibols), and 38 non-depsipeptide and non-peptaibiotic lipopeptides. Their sources, structural sequences, antibiotic activities (e.g. antibacterial, antifungal, antiviral, antimycobacterial, antimycoplasmal, antimalarial, antileishmanial, insecticidal, antitrypanosomal and nematicidal), structure-activity relationships, mechanisms of action, and specific relevance are discussed. These compounds have attracted considerable interest within the pharmaceutical and agrochemical industries.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
