Micafungin

Micafungin
Clinical data
Trade names	Mycamine
AHFS/Drugs.com	Monograph
License data	EU EMA: by INN; US DailyMed: Micafungin; US FDA: Micafungin;
Pregnancy; category	C;
Routes of; administration	Intravenous
ATC code	J02AX05 (WHO) ;
Legal status
Legal status	US: ℞-only ; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	99.8%
Metabolism	Via catechol-O-methyltransferase pathway
Elimination half-life	11–17 hours
Excretion	40% 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	235114-32-6 ;
PubChem CID	477468;
DrugBank	DB01141 ;
ChemSpider	21106351 ;
UNII	R10H71BSWG;
KEGG	D02465 ;
ChEMBL	ChEMBL1201351 ;
CompTox Dashboard (EPA)	DTXSID90873341 ;
Chemical and physical data
Formula	C56H71N9O23S
Molar mass	1270.28 g·mol−1
	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 ; Key:PIEUQSKUWLMALL-NFGJWQNFSA-N ;
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Micafungin, sold under the brand name Mycamine, is a polyene 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. Micafungin is administered intravenously. It received final approval from the U.S. Food and Drug Administration (FDA) on March 16, 2005, and gained approval in the European Union on April 25, 2008.

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. ^[1] ^[2]

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.^[3]^[4]

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.^[5]^[6]

References

^ 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.
^ 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.
^ Carver PL (October 2004). "Micafungin". The Annals of Pharmacotherapy. 38 (10): 1707–21. doi:10.1345/aph.1D301. PMID 15340133.
^ 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.
^ Hashimoto S (January 2009). "Micafungin: a sulfated echinocandin". The Journal of Antibiotics. 62 (1): 27–35. doi:10.1038/ja.2008.3. PMID 19132058.
^ 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.

External links

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

[1] 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.

[2] 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.

[3] Carver PL (October 2004). "Micafungin". The Annals of Pharmacotherapy. 38 (10): 1707–21. doi:10.1345/aph.1D301. PMID 15340133.

[4] 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.

[5] Hashimoto S (January 2009). "Micafungin: a sulfated echinocandin". The Journal of Antibiotics. 62 (1): 27–35. doi:10.1038/ja.2008.3. PMID 19132058.

[6] 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.

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