Details of the Drug

General Information of Drug (ID: DM6Y3AN)

• Drug Name: Micafungin
• Synonyms: Mycamine; FK463; FK-463; Mycamine (TN); Mycamine(TM)

Indication

Disease Entry	ICD 11	Status	REF
Aspergillosis	1F20	Approved	[1]
Candidiasis	1F23	Approved	[2]
Invasive aspergillosis	1F20.0	Approved	[1]
Invasive candidiasis	1F23	Approved	[1]
Candidemia	1F23.3Y	Investigative	[1]
Esophageal candidiasis	N.A.	Investigative	[1]

• Therapeutic Class: Antifungal Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 4:
  Molecular Weight (mw); 1270.3
  Logarithm of the Partition Coefficient (xlogp); -1.6
  Rotatable Bond Count (rotbonds); 18
  Hydrogen Bond Donor Count (hbonddonor); 16
  Hydrogen Bond Acceptor Count (hbondacc); 24
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 0.17 mL/min/kg [4]
  Elimination: 1% of drug is excreted from urine in the unchanged form [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 14 - 17 hours [4]
  Metabolism: The drug is metabolized via the arylsulfatase with further metabolism to M-2 (methoxy form) by catechol-O-methyltransferase []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.3 micromolar/kg/day [5]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.0023% [4]
  Vd: The volume of distribution (Vd) of drug is 0.39 +/- 0.11 L/kg []
• Chemical Identifiers:
  Formula: C56H71N9O23S
  IUPAC Name: [5-[(1S,2S)-2-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-[[4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzoyl]amino]-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl] hydrogen sulfate
  Canonical SMILES: CCCCCOC1=CC=C(C=C1)C2=CC(=NO2)C3=CC=C(C=C3)C(=O)N[C@H]4C[C@H]([C@H](NC(=O)[C@@H]5[C@H]([C@H](CN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H](NC4=O)[C@@H](C)O)O)[C@@H]([C@H](C7=CC(=C(C=C7)O)OS(=O)(=O)O)O)O)[C@@H](CC(=O)N)O)C)O)O)O
  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
  InChIKey: PIEUQSKUWLMALL-YABMTYFHSA-N
• Cross-matching ID:
  PubChem CID: 477468
  ChEBI ID: CHEBI:600520
  CAS Number: 235114-32-6
  DrugBank ID: DB01141
  TTD ID: D06TOE
  INTEDE ID: DR1083
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Fungal 1,3-beta-glucan synthase (Fung GSC2)	TT0SFXH	FKS2_YEAST	Modulator	[6]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Arylsulfatase A (ARSA) Main DME	DEJ6FSR	ARSA_HUMAN	Substrate	[7]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Micafungin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Lurbinectedin	DMEFRTZ	Moderate	Decreased metabolism of Micafungin caused by Lurbinectedin mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[8]
Everolimus	DM8X2EH	Moderate	Decreased metabolism of Micafungin caused by Everolimus mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[9]
LEE011	DMMX75K	Moderate	Decreased metabolism of Micafungin caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[10]

References

• [1] Micafungin FDA Label
• [2] Echinocandins: pharmacokinetic and therapeutic issues. Curr Med Res Opin. 2009 Jul;25(7):1741-50.
• [3] BDDCS applied to over 900 drugs
• [4] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [5] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [6] An immunomodulatory activity of micafungin in preclinical aspergillosis. J Antimicrob Chemother. 2014 Apr;69(4):1065-74.
• [7] The echinocandin micafungin: a review of the pharmacology, spectrum of activity, clinical efficacy and safety. Expert Opin Pharmacother. 2007 Jun;8(8):1155-66.
• [8] Product Information. Zepzelca (lurbinectedin). Jazz Pharmaceuticals, Palo Alto, CA.
• [9] Product Information. Afinitor (everolimus). Novartis Pharmaceuticals, East Hanover, NJ.
• [10] Cerner Multum, Inc. "Australian Product Information.".