Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H4ClNO2 |
Molecular Weight | 169.565 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C2OC(=O)NC2=C1
InChI
InChIKey=TZFWDZFKRBELIQ-UHFFFAOYSA-N
InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
Molecular Formula | C7H4ClNO2 |
Molecular Weight | 169.565 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.rxlist.com/chlorzoxazone-drug.htmCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68002753
Sources: http://www.rxlist.com/chlorzoxazone-drug.htm
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68002753
Chlorzoxazone is a centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex arcs involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles. Chlorzoxazone is indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Chlorzoxazone does not directly relax tense skeletal muscles in man.
CNS Activity
Originator
Sources: https://www.google.com/patents/US2895877
Curator's Comment: Marsh, D.F.; US. Patent 2,895,877; July 21, 1959; assigned to McNeil Laboratories, Inc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10712246 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CHLORZOXAZONE Approved UseINDICATIONS & USAGE SECTION Chlorzoxazone is indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Chlorzoxazone does not directly relax tense skeletal muscles in man. Launch Date5.7870719E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
36.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6631711/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.45 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
5.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
12.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
0.14 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4084 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6631711/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16.69 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.86 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
43.5 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
15.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
32.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
0.64 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.95 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6631711/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/25815637/ Page: 7.0 |
major | |||
Page: 1.0 |
minor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25815637/ Page: 7.0 |
minor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/25815637/ Page: 7.0 |
minor |
PubMed
Title | Date | PubMed |
---|---|---|
[Rhabdomyolysis and cholestatic hepatitis under treatment with simvastatin and chlorzoxazone]. | 1999 Apr 3 |
|
CYP2E1-dependent benzene toxicity: the role of extrahepatic benzene metabolism. | 1999 Jun-Jul |
|
Pharmacological activation of cloned intermediate- and small-conductance Ca(2+)-activated K(+) channels. | 2000 Mar |
|
EBIO, an agent causing maintained epithelial chloride secretion by co-ordinate actions at both apical and basolateral membranes. | 2001 |
|
Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. | 2001 Aug |
|
Genetic and dietary factors affecting human metabolism of 1,3-butadiene. | 2001 Jun 1 |
|
Tissue-specific alterations in the 6-hydroxylation of chlorzoxazone following traumatic brain injury in the rat. | 2001 Mar |
|
In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. | 2001 Mar |
|
Mitochondrial dysfunction by gamma-irradiation accompanies the induction of cytochrome P450 2E1 (CYP2E1) in rat liver. | 2001 Mar 21 |
|
Metabolism of vanoxerine, 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine, by human cytochrome P450 enzymes. | 2001 Sep |
|
Mechanism of aerobic transformation of carbon tetrachloride by poplar cells. | 2002 |
|
Validated HPLC method for determination of chlorzoxazone in human serum and its application in a clinical pharmacokinetic study. | 2002 Dec |
|
Effect of chronic disulfiram administration on the activities of CYP1A2, CYP2C19, CYP2D6, CYP2E1, and N-acetyltransferase in healthy human subjects. | 2002 Feb |
|
Cytochrome P450 enzymes contributing to demethylation of maprotiline in man. | 2002 Mar |
|
Effects of flavonoids isolated from Scutellariae radix on cytochrome P-450 activities in human liver microsomes. | 2002 Mar |
|
The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. | 2002 Mar |
|
Substrate specificity for rat cytochrome P450 (CYP) isoforms: screening with cDNA-expressed systems of the rat. | 2002 Mar 1 |
|
[Simultaneous determination of three probe drugs by reversed-phase high performance liquid chromatography]. | 2002 Nov |
|
Phenotype distribution and gender-related differences of CYP2E1 activity in a Chinese population. | 2002 Nov |
|
Cytochrome P450 2E1 expression induces hepatocyte resistance to cell death from oxidative stress. | 2002 Oct |
|
Lipopolysaccharide-mediated modulation of cytochromes P450 in Stat1 null mice. | 2003 Apr |
|
Effects of glucose on the pharmacokinetics of intravenous chlorzoxazone in rats with acute renal failure induced by uranyl nitrate. | 2003 Aug |
|
CYP2E1 activity before and after weight loss in morbidly obese subjects with nonalcoholic fatty liver disease. | 2003 Aug |
|
Rates of metabolism of chlorzoxazone, dextromethorphan, 7-ethoxycoumarin, imipramine, quinidine, testosterone and verapamil by fresh and cryopreserved rat liver slices, and some comparisons with microsomes. | 2003 Aug |
|
Simultaneous determination of aspirin and isosorbide 5-mononitrate in formulation by reversed phase high pressure liquid chromatography. | 2003 Aug 21 |
|
Study of the fragmentation mechanism of protonated 6-hydroxychlorzoxazone: application in simultaneous analysis of CYP2E1 activity with major human cytochrome P450s. | 2003 Feb 1 |
|
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
Determination of 6-hydroxychlorzoxazone and chlorzoxazone in porcine microsome samples. | 2003 Jan 25 |
|
Stimulatory effects of chlorzoxazone, a centrally acting muscle relaxant, on large conductance calcium-activated potassium channels in pituitary GH3 cells. | 2003 Jan 3 |
|
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel. | 2003 Jan-Feb |
|
Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: comparison with resveratrol and polyphenols from alcoholized beverages. | 2003 Jul 18 |
|
Diterpene quinone tanshinone IIA selectively inhibits mouse and human cytochrome p4501A2. | 2003 Jun |
|
Functional characterization of three human cytochrome p450 2E1 variants with amino acid substitutions. | 2003 Jun |
|
How useful is the "cocktail approach" for evaluating human hepatic drug metabolizing capacity using cytochrome P450 phenotyping probes in vivo? | 2003 Jun |
|
Metabolism of chloroform in the human liver and identification of the competent P450s. | 2003 Mar |
|
Effects of cigarette smoking and carbon monoxide on chlorzoxazone and caffeine metabolism. | 2003 Nov |
|
Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. | 2003 Nov |
|
GYKI-47261, a new AMPA [2-amino-3-(3-hydroxymethylisoxazole-4-yl)propionic acid] antagonist, is a CYP2E1 inducer. | 2003 Nov |
|
CYP2E1 regulation by benzene and other small organic chemicals in rat liver and peripheral lymphocytes. | 2003 Sep 15 |
|
ATP release triggered by activation of the Ca2+-activated K+ channel in human airway Calu-3 cells. | 2004 Mar |
Patents
Sample Use Guides
One tablet three or four times daily. If adequate response is not obtained with this dose, it may be increased to one and one-half tablets (750 mg) three or four times daily. As improvement occurs dosage can usually be reduced.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16859676
Chlorzoxazone did not affect the tension of the rat thoracic artery rings at rest, but relaxed the precontraction induced by 1 uM noradrenaline in an endothelium independent manner. Preincubation with chlorzoxazone also antagonized the contraction induced by 1 uM noradrenaline or 25 mM KCl.
Substance Class |
Chemical
Created
by
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on
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Sat Dec 17 18:02:21 UTC 2022
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on
Sat Dec 17 18:02:21 UTC 2022
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Record UNII |
H0DE420U8G
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LIVERTOX |
NBK548137
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NDF-RT |
N0000175737
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WHO-VATC |
QM03BB53
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WHO-ATC |
M03BB03
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WHO-VATC |
QM03BB03
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WHO-ATC |
M03BB53
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NDF-RT |
N0000175730
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WHO-ATC |
M03BB73
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NCI_THESAURUS |
C29696
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WHO-VATC |
QM03BB73
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202-403-9
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DTXSID9022813
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D002753
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H0DE420U8G
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H0DE420U8G
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2322
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95-25-0
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SUB06215MIG
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CHLORZOXAZONE
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2410
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CHEMBL1371
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3655
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748
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M3471
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1130505
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C28926
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626
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2733
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DB00356
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
further metabolized to glucoronide
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Cmax | PHARMACOKINETIC |
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ROUTE OF ADMINISTRATION PHARMACOKINETIC PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ROUTE OF ADMINISTRATION PHARMACOKINETIC PHARMACOKINETIC |
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