Chemistry:Micafungin

Short description: Chemical compound

Micafungin

Clinical data
Trade names	Mycamine
AHFS/Drugs.com	Monograph
License data	US DailyMed: Micafungin
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 Y
PubChem CID	477468
DrugBank	DB01141 Y
ChemSpider	21106351 Y
UNII	R10H71BSWG
KEGG	D02465 N
ChEMBL	ChEMBL1201351 N
Chemical and physical data
Formula	C56H71N9O23S
Molar mass	1270.28 g·mol−1
3D model (JSmol)	Interactive image
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
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Micafungin, sold under the brand name Mycamine, is an echinocandin 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.

Administered intravenously, Micafungin 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. It is on the World Health Organization's List of Essential Medicines.

In August 2023, Mycamine was acquired from Astellas Pharma by Sandoz.

Indications

Micafungin is indicated for the treatment of candidemia, acute disseminated candidiasis, Candida peritonitis, abscesses and esophageal candidiasis.

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.

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.

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.

Further reading

• "Comparison of echinocandin antifungals". Therapeutics and Clinical Risk Management 3 (1): 71–97. March 2007. doi:10.2147/tcrm.2007.3.1.71. PMID 18360617.