Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H12N2O2S |
Molecular Weight | 236.29 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(N(O)C(N)=O)C1=CC2=C(S1)C=CC=C2
InChI
InChIKey=MWLSOWXNZPKENC-UHFFFAOYSA-N
InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)
Molecular Formula | C11H12N2O2S |
Molecular Weight | 236.29 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Zileuton is an asthma drug that differs chemically and pharmacologically from other antiasthmatic agents. It blocks leukotriene synthesis by inhibiting 5-lipoxygenase, an enzyme of the eicosanoid synthesis pathway. Current data indicates that asthma is a chronic inflammatory disorder of the airways involving the production and activity of several endogenous inflammatory mediators, including leukotrienes. Sulfido-peptide leukotrienes (LTC4, LTD4, LTE4, also known as the slow-releasing substances of anaphylaxis) and LTB4, a chemoattractant for neutrophils and eosinophils, are derived from the initial unstable product of arachidonic acid metabolism, leukotriene A4 (LTA4), and can be measured in a number of biological fluids including bronchoalveolar lavage fluid (BALF) from asthmatic patients. In humans, pretreatment with zileuton attenuated bronchoconstriction caused by cold air challenge in patients with asthma. Zileuton is a specific inhibitor of 5-lipoxygenase and thus inhibits leukotriene (LTB4, LTC4, LTD4, and LTE4) formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in in vitro systems. Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton is marketed under the trade name ZYFLO.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZYFLO Approved UseZYFLO is indicated for the prophylaxis and chronic treatment of asthma in adults and
children 12 years of age and older. Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.15 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
4.25 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
5.69 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
4.82 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.55 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
7.13 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.63 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
7.47 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.98 μg/mL |
600 mg 4 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZILEUTON plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.28 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
19.1 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
26.34 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
23.23 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
29.09 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
28.03 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
30.18 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
26.51 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
19.2 μg × h/mL |
600 mg 4 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZILEUTON plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
2.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
2.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.08% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
6.98% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.23% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
6.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.04% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
7.01% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.32% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
|
6.73% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8620670/ |
600 mg 4 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZILEUTON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7% |
600 mg 4 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZILEUTON plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition by troglitazone of the antigen-induced production of leukotrienes in immunoglobulin E-sensitized RBL-2H3 cells. | 2000 Jan |
|
Role of petasin in the potential anti-inflammatory activity of a plant extract of petasites hybridus. | 2001 Apr 15 |
|
Zileuton and atopic dermatitis. | 2001 Aug |
|
Involvement of leukotriene B(4) in substance P-induced itch-associated response in mice. | 2001 Dec |
|
Role of the IgE-mediated system in eosinophil recruitment triggered by two consecutive cycles of sensitisation and challenge in rats. | 2001 Dec |
|
Clinical and biochemical effects of zileuton in patients with the Sjögren-Larsson syndrome. | 2001 Dec |
|
Leukotriene inhibitors and non-steroidal therapies in the treatment of asthma. | 2001 Jan |
|
Efficacy of antileukotriene agents in asthma management. | 2001 Jun |
|
Discovery of leukotrienes and development of antileukotriene agents. | 2001 Jun |
|
The role of antileukotrienes in the treatment of asthma. | 2001 Jun |
|
Safety of antileukotriene agents in asthma management. | 2001 Jun |
|
Antileukotrienes in asthma: present situation. | 2001 Mar |
|
Leukotrienes play protective roles early during experimental VSV encephalitis. | 2001 Nov 1 |
|
Acute effects of the cys-leukotriene-1 receptor antagonist, montelukast, on experimental colitis in rats. | 2001 Oct 19 |
|
Leukotrienes in respiratory disease. | 2001 Sep |
|
Effects of Celebrex and Zyflo on BOP-induced pancreatic cancer in Syrian hamsters. | 2002 |
|
Pharmacogenetics, pharmacogenomics and airway disease. | 2002 |
|
Treatment of disseminated granuloma annulare with a 5-lipoxygenase inhibitor and vitamin E. | 2002 Apr |
|
Monocyte chemoattractant protein-1 and 5-lipoxygenase products recruit leukocytes in response to platelet-activating factor-like lipids in oxidized low-density lipoprotein. | 2002 Apr 15 |
|
Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice. | 2002 Aug 1 |
|
[Anti-leukotriene drugs and Churg Strauss syndrome]. | 2002 Feb |
|
Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase II: in vivo studies. | 2002 Feb |
|
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes. | 2002 Jul |
|
Thioglycollate peritonitis in mice lacking C5, 5-lipoxygenase, or p47(phox): complement, leukotrienes, and reactive oxidants in acute inflammation. | 2002 Mar |
|
Role of Ca(2+)-independent phospholipase A(2) and cyclooxygenase/lipoxygenase pathways in the nitric oxide production by murine macrophages stimulated by lipopolysaccharides. | 2002 May |
|
[New horizons in the treatment of atopic dermatitis]. | 2002 May-Jun |
|
The effect of leukotriene-modifier drugs on aspirin-induced asthma and rhinitis reactions. | 2002 Oct |
|
Interaction between nitric oxide, reactive oxygen intermediates, and peroxynitrite in the regulation of 5-lipoxygenase metabolism. | 2002 Oct 10 |
|
Mediators of adenosine- and ovalbumen-induced bronchoconstriction of sensitized guinea-pig isolated airways. | 2002 Sep 6 |
|
Leukotrienes, IL-13, and chemokines cooperate to induce BHR and mucus in allergic mouse lungs. | 2003 Feb |
|
The role of leukotriene inhibitors in patients with paranasal sinus disease. | 2003 Jun |
|
Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. | 2003 Nov |
|
Inhibition of neutrophil leukotriene B4 production by a novel synthetic N-3 polyunsaturated fatty acid analogue, beta-oxa 21:3n-3. | 2003 Nov 1 |
|
Deficiency of NADPH oxidase components p47phox and gp91phox caused granulomatous synovitis and increased connective tissue destruction in experimental arthritis models. | 2003 Oct |
|
Zileuton, a 5-lipoxygenase inhibitor, increases production of thromboxane A2 and platelet aggregation in patients with asthma. | 2003 Sep |
|
Tenofovir, COX inhibitors and zileuton during cancer immunotherapies: up-regulated TNF-alpha increases antigen driven lymphocyte proliferation. | 2003 Sep |
|
Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro. | 2004 Nov |
|
Zileuton, an oral 5-lipoxygenase inhibitor, directly reduces sebum production. | 2005 |
|
Leukotrienes: their role in the treatment of asthma and seasonal allergic rhinitis. | 2005 Jan-Feb |
|
5-Lipoxygenase modulates colitis through the regulation of adhesion molecule expression and neutrophil migration. | 2005 Jun |
Sample Use Guides
The recommended dosage of ZYFLO (Zileuton) for the symptomatic treatment of patien ts with
asthma is one 600-mg tablet four times a day for a total daily dose of 2400 mg. For ease
of administration, ZYFLO may be taken with meals and at bedtime.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10319915
Zileuton (5 uM) inhibited LTB4 production by 99% in purified human neutrophils in the presence of fatty acid saturated albumin (fraction V).
Substance Class |
Chemical
Created
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on
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Record UNII |
V1L22WVE2S
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Record Status |
Validated (UNII)
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NDF-RT |
N0000008683
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NDF-RT |
N0000175956
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LIVERTOX |
NBK548397
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NCI_THESAURUS |
C1322
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N0000175955
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N0000008683
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Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
FECAL; URINE
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN-VITRO
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
IN-VITRO
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Route of Elimination | PHARMACOKINETIC |
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