Micafungin

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Micafungin
Clinical data
Trade namesMycamine
AHFS/Drugs.comMonograph
License data
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
  • {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
JSmol)
  • 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=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 checkY
  • Key:PIEUQSKUWLMALL-NFGJWQNFSA-N checkY
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Micafungin, sold under the brand name Mycamine, is an

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.[1]

In August 2023, Mycamine was acquired from Astellas Pharma by Sandoz.[2]

Indications

Micafungin is

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. [3] [4]

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.[5][6]

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.[7][8]

References

  1. hdl:10665/345533
    . WHO/MHP/HPS/EML/2021.02.
  2. ^ Dharma RK (28 August 2023). "Sandoz concludes acquisition of Mycamine antifungal agent". Pharmaceutical Technology. Retrieved 29 August 2023.
  3. PMID 17806055
    .
  4. S2CID 31500007
    .
  5. S2CID 265942428
    .
  6. S2CID 10873612
    .
  7. PMID 19132058
    .
  8. doi:10.1351/pac200779040603
    .

Further reading
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