Micafungin

Micafungin, sold under the brand name Mycamine, is an echinochandin antifungal medication used to treat and prevent invasive fungal infections including candidemia, abscesses, and esophageal candidiasis. It inhibits the production of beta-1,3-glucan, an essential component of fungal cell walls that is not found in mammals. Micafungin is administered intravenously. It received final approval from the U.S. Food and Drug Administration (FDA) in March 2005, and gained approval in the European Union in April 2008.

Micafungin
Clinical data
Trade namesMycamine
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • C
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding99.8%
MetabolismVia catechol-O-methyltransferase pathway
Elimination half-life11–17 hours
Excretion40% feces, <15% urine
Identifiers
IUPAC name
  • {5-[(1S,2S)-2-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-3-[(1R)-2-carbamoyl-1-hydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-[(4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzene)amido]-1,4,7,13,16,22-hexaazatricyclo[22.3.0.09,13]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC56H71N9O23S
Molar mass1270.28 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCOc1ccc(-c2cc(-c3ccc(C(=O)N[C@H]4C[C@@H](O)[C@@H](O)N=C(O)[C@@H]5[C@@H](O)[C@@H](C)CN5C(=O)[C@H]([C@H](O)CC(=N)O)N=C(O)[C@H]([C@H](O)[C@@H](O)c5ccc(O)c(OS(=O)(=O)O)c5)N=C(O)[C@@H]5C[C@@H](O)CN5C(=O)[C@H]([C@H](C)O)N=C4O)cc3)no2)cc1
InChI
  • InChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26-,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1 Y
  • Key:PIEUQSKUWLMALL-NFGJWQNFSA-N Y
 NY (what is this?)  (verify)

It is on the World Health Organization's List of Essential Medicines.[1]

Indications

Micafungin is indicated for the treatment of candidemia, acute disseminated candidiasis, Candida peritonitis, abscesses and esophageal candidiasis. Since January 23, 2008, micafungin has been approved for the prophylaxis of Candida infections in patients undergoing hematopoietic stem cell transplantation (HSCT).

Micafungin works by way of concentration-dependent inhibition of 1,3-beta-D-glucan synthase resulting in reduced formation of 1,3-beta-D-glucan, which is an essential polysaccharide comprising one-third of the majority of Candida spp. cell walls. This decreased glucan production leads to osmotic instability and thus cellular lysis. [2] [3]

Dosage

The metabolism of micafungin occurs hepatically via acryp sulfatase followed by secondary metabolism by a transferase. Precautions should be taken with regards to dosing, as micafungin weakly inhibits CYP3A4.[4][5]

Dosage forms

Micafungin is a natural antifungal product derived from other fungi as a defense mechanism for competition of nutrients, etc. To be specific, micafungin is derived from FR901379, and is produced by Coleophoma empetri.[6][7]

References
  1. World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  2. Pappas PG, Rotstein CM, Betts RF, Nucci M, Talwar D, De Waele JJ, et al. (October 2007). "Micafungin versus caspofungin for treatment of candidemia and other forms of invasive candidiasis". Clinical Infectious Diseases. 45 (7): 883–93. doi:10.1086/520980. PMID 17806055.
  3. Pettengell K, Mynhardt J, Kluyts T, Lau W, Facklam D, Buell D (August 2004). "Successful treatment of oesophageal candidiasis by micafungin: a novel systemic antifungal agent". Alimentary Pharmacology & Therapeutics. 20 (4): 475–81. doi:10.1111/j.1365-2036.2004.02083.x. PMID 15298643. S2CID 31500007.
  4. Carver PL (October 2004). "Micafungin". The Annals of Pharmacotherapy. 38 (10): 1707–21. doi:10.1345/aph.1D301. PMID 15340133.
  5. Kohno S, Masaoka T, Yamaguchi H, Mori T, Urabe A, Ito A, et al. (2004). "A multicenter, open-label clinical study of micafungin (FK463) in the treatment of deep-seated mycosis in Japan". Scandinavian Journal of Infectious Diseases. 36 (5): 372–9. doi:10.1080/00365540410020406. PMID 15287383. S2CID 10873612.
  6. Hashimoto S (January 2009). "Micafungin: a sulfated echinocandin". The Journal of Antibiotics. 62 (1): 27–35. doi:10.1038/ja.2008.3. PMID 19132058.
  7. Fujie A (2007). "Discovery of micafungin (FK463): A novel antifungal drug derived from a natural product lead". Pure and Applied Chemistry. 79 (4): 603–614. doi:10.1351/pac200779040603.

Further reading
  • "Micafungin". Drug Information Portal. U.S. National Library of Medicine.
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