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 |
|
Metabolism of benzene in human liver microsomes: individual variations in relation to CYP2E1 expression. | 1999 Feb |
|
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 |
|
High-throughput cytochrome P450 (CYP) inhibition screening via a cassette probe-dosing strategy. VI. Simultaneous evaluation of inhibition potential of drugs on human hepatic isozymes CYP2A6, 3A4, 2C9, 2D6 and 2E1. | 2001 |
|
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes. | 2001 Feb |
|
Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia. | 2001 Feb |
|
Characterization of xenobiotic-metabolizing cytochrome P450 (CYP) forms in ringed and grey seals from the Baltic Sea and reference sites. | 2001 Jan |
|
One hundred percent online identity check of pharmaceutical products by near-infrared spectroscopy on the packaging line. | 2001 Jan |
|
Synthetic chloride channel restores glutathione secretion in cystic fibrosis airway epithelia. | 2001 Jul |
|
Genetic repeat polymorphism in the regulating region of CYP2E1: frequency and relationship with enzymatic activity in alcoholics. | 2001 Jun |
|
Identification of multiple constitutive and inducible hepatic cytochrome P450 enzymes in market weight swine. | 2001 Jun |
|
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline. | 2001 Mar |
|
Cytochrome P450 expression and related metabolism in human buccal mucosa. | 2001 Mar |
|
Cytochrome p450-dependent metabolism of trichloroethylene in rat kidney. | 2001 Mar |
|
Modulation of recombinant small-conductance Ca(2+)-activated K(+) channels by the muscle relaxant chlorzoxazone and structurally related compounds. | 2001 Mar |
|
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 |
|
A comparison of aroclor 1254-induced and uninduced rat liver microsomes to human liver microsomes in phenytoin O-deethylation, coumarin 7-hydroxylation, tolbutamide 4-hydroxylation, S-mephenytoin 4'-hydroxylation, chloroxazone 6-hydroxylation and testosterone 6beta-hydroxylation. | 2001 May 16 |
|
In vitro evaluation of valproic acid as an inhibitor of human cytochrome P450 isoforms: preferential inhibition of cytochrome P450 2C9 (CYP2C9). | 2001 Nov |
|
Contribution of CYP1A2 in the hepatic metabolism of melatonin: studies with isolated microsomal preparations and liver slices. | 2001 Nov |
|
Low doses of nicotine and ethanol induce CYP2E1 and chlorzoxazone metabolism in rat liver. | 2001 Nov |
|
Mechanism of aerobic transformation of carbon tetrachloride by poplar cells. | 2002 |
|
Effect of methacrylonitrile on cytochrome P-450 2E1 (CYP2E1) expression in male F344 rats. | 2002 Apr 12 |
|
Validated HPLC method for determination of chlorzoxazone in human serum and its application in a clinical pharmacokinetic study. | 2002 Dec |
|
The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. | 2002 Mar |
|
Plasma levels of TNF-alpha and IL-6 are inversely related to cytochrome P450-dependent drug metabolism in patients with congestive heart failure. | 2002 Oct |
|
Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption. | 2002 Oct |
|
Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. | 2002 Oct 1 |
|
Cytochrome P450 2E1 and 3A activities do not differ between Mexicans and European Americans. | 2002 Sep |
|
Characterization of vectorial chloride transport pathways in the human pancreatic duct adenocarcinoma cell line HPAF. | 2003 Aug |
|
Simultaneous determination of aspirin and isosorbide 5-mononitrate in formulation by reversed phase high pressure liquid chromatography. | 2003 Aug 21 |
|
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 |
|
Functional characterization of three human cytochrome p450 2E1 variants with amino acid substitutions. | 2003 Jun |
|
Cytochrome P450 expression and testosterone metabolism in the liver of deer. | 2003 May 1 |
|
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
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on
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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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100000081896
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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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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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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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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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