Micafungin

Micafungin
Clinical data
Trade names	Mycamine
AHFS/Drugs.com	Monograph
License data	EU EMA: by INN; US FDA: Micafungin;
Pregnancy; category	C;
Routes of; administration	Intravenous
ATC code	J02AX05 (WHO) ;
Legal status
Legal status	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 ;
Chemical and physical data
Formula	C56H71N9O23S
Molar mass	1270.28 g/mol
	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 (trade name Mycamine) is an echinocandin antifungal drug 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 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]

Contraindications

Known hypersensitivity to micafungin or any other ingredient contained in the formulation is a contraindication for its use.

Dosage

The metabolism of micafungin occurs hepatically as the drug molecule is a substrate of CYP3A4, a liver enzyme. Precautions should be taken with regards to dosing, as micafungin also inhibits its own clearance via weak CYP3A4 inhibition.^[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, P. G.; Rotstein, C. M.; Betts, R. F.; Nucci, M; Talwar, D; De Waele, J. J.; Vazquez, J. A.; Dupont, B. F.; Horn, D. L.; Ostrosky-Zeichner, L; Reboli, A. C.; Suh, B; Digumarti, R; Wu, C; Kovanda, L. L.; Arnold, L. J.; Buell, D. N. (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; FK463 South African Study Group (2004). "Successful treatment of oesophageal candidiasis by micafungin: A novel systemic antifungal agent". Alimentary Pharmacology and Therapeutics. 20 (4): 475–81. doi:10.1111/j.1365-2036.2004.02083.x. PMID 15298643.
↑ Carver, P. L. (2004). "Micafungin". 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; Niki, Y; Ikemoto, H (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.
↑ Hashimoto, S (2009). "Micafungin: A sulfated echinocandin". The Journal of Antibiotics. 62 (1): 27–35. doi:10.1038/ja.2008.3. PMID 19132058.
↑ Fujie, Akihiko (2007). "Discovery of micafungin (FK463): A novel antifungal drug derived from a natural product lead". Pure and Applied Chemistry. 79 (4). doi:10.1351/pac200779040603.

External links

Mycamine website, run by Astellas Pharma US
Mycamine Prescribing Information
Eschenauer, G; Depestel, D. D.; Carver, P. L. (2007). "Comparison of echinocandin antifungals". Therapeutics and Clinical Risk Management. 3 (1): 71–97. doi:10.2147/tcrm.2007.3.1.71. PMC 1936290. PMID 18360617.

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[1] Pappas, P. G.; Rotstein, C. M.; Betts, R. F.; Nucci, M; Talwar, D; De Waele, J. J.; Vazquez, J. A.; Dupont, B. F.; Horn, D. L.; Ostrosky-Zeichner, L; Reboli, A. C.; Suh, B; Digumarti, R; Wu, C; Kovanda, L. L.; Arnold, L. J.; Buell, D. N. (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; FK463 South African Study Group (2004). "Successful treatment of oesophageal candidiasis by micafungin: A novel systemic antifungal agent". Alimentary Pharmacology and Therapeutics. 20 (4): 475–81. doi:10.1111/j.1365-2036.2004.02083.x. PMID 15298643.

[3] Carver, P. L. (2004). "Micafungin". 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; Niki, Y; Ikemoto, H (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.

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

[6] Fujie, Akihiko (2007). "Discovery of micafungin (FK463): A novel antifungal drug derived from a natural product lead". Pure and Applied Chemistry. 79 (4). doi:10.1351/pac200779040603.