zileuton ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2862 111406-87-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zileuton
  • leutrol
  • A-64077
  • A 64077
an orally active inhibitor of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid
  • Molecular weight: 236.29
  • Formula: C11H12N2O2S
  • CLOGP: 2.48
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 66.56
  • ALOGS: -3.64
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.50 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 169.28 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Dec. 9, 1996 FDA CHIESI USA INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Asthma 48.26 37.44 19 312 89318 50515475

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
FDA PE N0000008683 Decreased Leukotriene Production
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006727 Hormone Antagonists
MeSH PA D020024 Leukotriene Antagonists
MeSH PA D016859 Lipoxygenase Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory agent
CHEBI has role CHEBI:49159 leukotriene antagonists
CHEBI has role CHEBI:49167 anti-asthmatic drugs
CHEBI has role CHEBI:64964 5delta-lipoxygenase inhibitor
CHEBI has role CHEBI:173084 ferroptosis inhibitors
FDA MoA N0000175955 5-Lipoxygenase Inhibitors
FDA EPC N0000175956 5-Lipoxygenase Inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Non-allergic asthma indication 266361008 DOID:9360
Allergic asthma indication 389145006 DOID:9415
Asthma management indication 406162001
Suicidal thoughts contraindication 6471006
Hallucinations contraindication 7011001
Mood swings contraindication 18963009
Feeling agitated contraindication 24199005
Depressive disorder contraindication 35489007
Anxiety contraindication 48694002
Dream disorder contraindication 85418005
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Tremors contraindication
Nervousness contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.96 acidic
pKa2 13.02 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Arachidonate 5-lipoxygenase Enzyme INHIBITOR IC50 6.52 CHEMBL CHEMBL
Arachidonate 15-lipoxygenase Enzyme IC50 6.40 CHEMBL
Cysteinyl leukotriene receptor 2 GPCR IC50 5.82 WOMBAT-PK
Leukotriene A-4 hydrolase Enzyme IC50 6.07 WOMBAT-PK
Leukotriene B4 receptor 1 GPCR IC50 6.38 CHEMBL
Arachidonate 5-lipoxygenase-activating protein Cytosolic other IC50 5.66 CHEMBL
Bifunctional epoxide hydrolase 2 Enzyme IC50 6.23 CHEMBL
Prostaglandin E synthase Enzyme IC50 6.22 CHEMBL
Arachidonate 5-lipoxygenase Enzyme IC50 6.85 CHEMBL
Arachidonate 5-lipoxygenase Enzyme IC50 6.72 CHEMBL

External reference:

IDSource
4021009 VUID
N0000148478 NUI
D00414 KEGG_DRUG
4021009 VANDF
C0081408 UMLSCUI
CHEBI:10112 CHEBI
CHEMBL93 ChEMBL_ID
DB00744 DRUGBANK_ID
60490 PUBCHEM_CID
6595 INN_ID
C063449 MESH_SUPPLEMENTAL_RECORD_UI
5297 IUPHAR_LIGAND_ID
V1L22WVE2S UNII
40575 RXNORM
254934 MMSL
5704 MMSL
d04103 MMSL
006297 NDDF
108617005 SNOMEDCT_US
386180009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ZYFLO HUMAN PRESCRIPTION DRUG LABEL 1 10122-901 TABLET 600 mg ORAL NDA 14 sections
Zileuton HUMAN PRESCRIPTION DRUG LABEL 1 49884-723 TABLET, MULTILAYER, EXTENDED RELEASE 600 mg ORAL ANDA 27 sections
Zileuton Human Prescription Drug Label 1 64980-206 TABLET, EXTENDED RELEASE 600 mg ORAL ANDA 17 sections
Zileuton HUMAN PRESCRIPTION DRUG LABEL 1 66993-485 TABLET, EXTENDED RELEASE 600 mg ORAL NDA authorized generic 25 sections
ZILEUTON HUMAN PRESCRIPTION DRUG LABEL 1 68180-169 TABLET, EXTENDED RELEASE 600 1 ORAL ANDA 24 sections
Zileuton HUMAN PRESCRIPTION DRUG LABEL 1 69339-130 TABLET, MULTILAYER, EXTENDED RELEASE 600 mg ORAL ANDA 27 sections