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Showing drug card for Micafungin (DB01141)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:21
Primary Accession Number DB01141
Secondary Accession Number
  • APRD01114
Name Micafungin
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Micafungin is an antifungal drug. It belongs to the antifungal class of compounds known as echinocandins and exerts its effect by inhibiting the synthesis of 1,3-beta-D-glucan, an integral component of the fungal cell wall.
Synonyms
  1. FK-463
  2. micafungin
Brand Names
  1. Mycamine
Brand Mixtures Not Available
Chemical IUPAC Name Not Available
Chemical Formula C56H71N9O23S
Chemical Structure Structure
CAS Registry Number 235114-32-6
InChI Identifier InChI=1/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)/f/h58-62,83H,57H2
InChI Key PIEUQSKUWLMALL-PMEIKOPDCK
KEGG Drug D02465 Link Image
KEGG Compound C15819 Link Image
PubChem Compound 3081921 Link Image
PubChem Substance 3884856 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic4/mycamine.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Micafungin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 1270.2740
Monoisotopic Molecular Weight 1269.4384
State Solid
Melting Point Not Available
Experimental Water Solubility Freely soluble as sodium salt (> 200mg/mL) Source: PhysProp
Predicted Water Solubility 2.18e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -1.5 Source: PhysProp
Predicted LogP 0.67 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.77 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCCCCOC1=CC=C(C=C1)C1=CC(=NO1)C1=CC=C(C=C1)C(=O)N[C@@H]1C[C@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@H](C)CN2C(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H]2C[C@H](O)CN2C(=O)[C@H](NC1=O)[C@@H](C)O)[C@H](O)[C@H](O)C1=CC(OS(O)(=O)=O)=C(O)C=C1)[C@@H](O)CC(N)=O
Canonical SMILES CCCCCOC1=CC=C(C=C1)C1=CC(=NO1)C1=CC=C(C=C1)C(=O)NC1CC(O)C(O)NC(=O)C2C(O)C(C)CN2C(=O)C(NC(=O)C(NC(=O)C2CC(O)CN2C(=O)C(NC1=O)C(C)O)C(O)C(O)C1=CC(OS(O)(=O)=O)=C(O)C=C1)C(O)CC(N)=O
Drug Category
  • Antifungal Agents
  • Antifungals
ATC Codes
AHFS Codes Not Available
Indication For use in the treatment of patients with esophageal candidiasis and prophylaxis of Candida infections in patients undergoing hematopoietic stem cell transplantation.
Pharmacology Formerly known as FK463, micafungin is a novel antifungal agent. It is a glucan synthesis inhibitor of the echinocandin structural class. The U.S. Food and Drug Administration approved micafungin in March 2005. Micafungin inhibits an enzyme essential for fungal cell-wall synthesis and is fungicidal (lethal) for Candida. Micafungin can be used concomitantly with a variety of other drugs, including the HIV protease inhibitor ritonavir and the transplant medications cyclosporine and tacrolimus.
Mechanism of Action Micafungin inhibits the synthesis of 1,3-b-D-glucan, an essential component of fungal cell walls, which is not present in mammalian cells.
Absorption Not Available
Toxicity Intravenous LD50 in rats is 125mg/kg. In dogs it is >200mg/kg. No cases of overdosage have been reported. Repeated daily doses up to 8 mg/kg (maximum total dose of 896 mg) in adult patients have been administered in clinical trials with no reported dose-limiting toxicity. The minimum lethal dose is 125 mg/kg in rats, equivalent to 8.1 times the recommended human clinical dose for esophageal candidiasis based on body surface area comparisons.
Protein Binding Highly (>99%) protein bound in vitro, independent of plasma concentrations over the range of 10 to 100 µg/mL. The primary binding protein is albumin; however, micafungin, at therapeutically relevant concentrations, does not competitively displace bilirubin binding to albumin. Micafungin also binds to a lesser extent to a1-acid-glycoprotein.
Biotransformation Micafungin is metabolized to M-1 (catechol form) by arylsulfatase, with further metabolism to M-2 (methoxy form) by catechol-O-methyltransferase. M-5 is formed by hydroxylation at the side chain (w-1 position) of micafungin catalyzed by cytochrome P450 (CYP) isozymes. Even though micafungin is a substrate for and a weak inhibitor of CYP3A in vitro, hydroxylation by CYP3A is not a major pathway for micafungin metabolism in vivo.
Half Life 14-17 hours
Dosage Forms
Form Route
Injection, powder, lyophilized, for solution Intravenous drip
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Aspergillis, Candida and other fungi
Phase 1 Metabolizing Enzymes
  1. Arylsulfatase A
Targets
  1. Beta-1,3-glucan synthase
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Arylsulfatase A
Enzyme 1 Gene Name ARSA
Enzyme 1 SwissProt ID P15289 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P15289|ARSA_HUMAN Arylsulfatase A 
MGAPRSLLLALAAGLAVARPPNIVLIFADDLGYGDLGCYGHPSSTTPNLDQLAAGGLRFT
DFYVPVSLCTPSRAALLTGRLPVRMGMYPGVLVPSSRGGLPLEEVTVAEVLAARGYLTGM
AGKWHLGVGPEGAFLPPHQGFHRFLGIPYSHDQGPCQNLTCFPPATPCDGGCDQGLVPIP
LLANLSVEAQPPWLPGLEARYMAFAHDLMADAQRQDRPFFLYYASHHTHYPQFSGQSFAE
RSGRGPFGDSLMELDAAVGTLMTAIGDLGLLEETLVIFTADNGPETMRMSRGGCSGLLRC
GKGTTYEGGVREPALAFWPGHIAPGVTHELASSLDLLPTLAALAGAPLPNVTLDGFDLSP
LLLGTGKSPRQSLFFYPSYPDEVRGVFAVRTGKYKAHFFTQGSAHSDTTADPACHASSSL
TAHEPPLLYDLSKDPGENYNLLGGVAGATPEVLQALKQLQLLKAQLDAAVTFGPSQVARG
EDPALQICCHPGCTPRPACCHCPDPHA
Drug Target 1 [top]
Target 1 ID 351
Target 1 Name Beta-1,3-glucan synthase
Target 1 Synonyms
  1. EC 2.4.1.34
Target 1 Gene Name Not Available
Target 1 Protein Sequence >Beta-1,3-glucan synthase 
DANQDNYLEECLKIRSVLAEFEELTTDNVSPYTPGIATEAETPVAILGAREYIFSENVGV
LGDVAASKEQTFGTLFARTLAQIGGKLHYGHPDFLNGIFMTTRGGISKAQKGLHLNEDIY
AG
Target 1 Number of Residues 124
Target 1 Molecular Weight 13224
Target 1 Theoretical pI 4.43
Target 1 GO Classification
Function
catalytic activity
transferase activity
transferase activity, transferring glycosyl groups
UDP-glycosyltransferase activity
UDP-glucosyltransferase activity
1,3-beta-glucan synthase activity
Process
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
polysaccharide metabolism
cellular polysaccharide metabolism
glucan metabolism
beta-glucan metabolism
beta-1,3 glucan metabolism
beta-1,3 glucan biosynthesis
Component
cell
membrane
protein complex
1,3-beta-glucan synthase complex
Target 1 General Function Involved in 1,3-beta-glucan synthase activity
Target 1 Specific Function Not Available
Target 1 Pathways
Name SMPDB Link KEGG Link
Starch and sucrose metabolism SMP00058 Link Image map00500 Link Image
Target 1 Reactions
  • UDP-glucose + (1,3-beta-D-glucosyl)n = UDP + (1,3-beta-D-glucosyl)n+1
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 42716259 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q5DRK6 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q5DRK6_ASPNG Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >365 bp 
GACGCGAATCAGGATAACTACCTGGAGGAGTGTCTCAAGATCCGTAGCGTTCTGGCTGAG
TTCGAAGAACTTACCACCGACAATGTCTCGCCCTACACTCCTGGTATTGCCACCGAAGCT
GAGACCCCAGTCGCCATTCTCGGTGCTCGTGAATACATTTTCTCTGAGAATGTTGGTGTT
CTTGGTGACGTTGCTGCCAGTAAGGAACAGACGTTCGGTACCCTGTTTGCTCGTACCCTT
GCGCAGATTGGTGGAAAGCTGCATTATGGTCACCCTGATTTCCTAAACGGTATCTTCATG
ACGACGCGTGGTGGTATCTCCAAGGCTCAGAAGGGTCTCCACCTGAATGAAGACATCTAC
GCCGG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs Not Available
Target 1 General References Not Available
Target 1 Drug References
  1. Georgopapadakou NH: Update on antifungals targeted to the cell wall: focus on beta-1,3-glucan synthase inhibitors. Expert Opin Investig Drugs. 2001 Feb;10(2):269-80. [PubMed Link Image]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  3. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.