Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H10ClN3O3 |
Molecular Weight | 315.711 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C3=C(Cl)C=CC=C3)C=C1
InChI
InChIKey=DGBIGWXXNGSACT-UHFFFAOYSA-N
InChI=1S/C15H10ClN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20)
Molecular Formula | C15H10ClN3O3 |
Molecular Weight | 315.711 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Clonazepam, a benzodiazepine, is used primarily as an anticonvulsant in the treatment of absence seizures, petit mal variant seizures (Lennox-Gastaut syndrome), akinetic and myoclonic seizures, and nocturnal myoclonus. Klonopin is the brand name for Clonazepam, an anxiolytic and anticonvulsant. The precise mechanism by which clonazepam exerts its antiseizure
and antipanic effects is unknown, although it is believed to be related to its ability to
enhance the activity of gamma aminobutyric acid (GABA), the major inhibitory
neurotransmitter in the central nervous system. Allosteric interactions between central benzodiazepine receptors and gamma-aminobutyric acid (GABA) receptors potentiate the effects of GABA. As GABA is an inhibitory neurotransmitter, this results in increased inhibition of the ascending reticular activating system. Benzodiazepines, in this way, block the cortical and limbic arousal that occurs following stimulation of the reticular pathways.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.06 nM [EC50] | |||
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25798598 |
57.0 µM [EC50] | ||
Target ID: CHEMBL2111413 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25798598 |
40.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | KLONOPIN Approved UseINDICATIONS & USAGE Seizure Disorders: Clonazepam tablets, USP are useful alone or as an adjunct in the treatment of the Lennox-Gastaut syndrome (petit mal variant), akinetic and . In patients with absence seizures (petit mal) who have failed to respond to succinimides, clonazepam may be useful. In some studies, up to 30% of patients have shown a loss of anticonvulsant activity, often within 3 months of administration. In some cases, dosage adjustment may reestablish efficacy.
Panic Disorder: Clonazepam tablets, USP are indicated for the treatment of panic disorder, with or without agoraphobia, as defined in DSM-IV. Panic disorder is characterized by the occurrence of unexpected panic attacks and associated concern about having additional attacks, worry about the implications or consequences of the attacks, and/or a significant change in behavior related to the attacks. The efficacy of clonazepam was established in two 6- to 9-week trials in panic disorder patients whose diagnoses corresponded to the DSM-IIIR category of panic disorder. Panic disorder (DSM-IV) is characterized by recurrent unexpected panic attacks, ie, a discrete period of intense fear or discomfort in which four (or more) of the following symptoms develop abruptly and reach a peak within 10 minutes: (1) palpitations, pounding heart or accelerated heart rate; (2) sweating; (3) trembling or shaking; (4) sensations of shortness of breath or smothering; (5) feeling of choking; (6) chest pain or discomfort; (7) nausea or abdominal distress; (8) feeling dizzy, unsteady, lightheaded or faint; (9) derealization (feelings of unreality) or depersonalization (being detached from oneself); (10) fear of losing control; (11) fear of dying; (12) paresthesias (numbness or tingling sensations); (13) chills or hot flushes. The effectiveness of clonazepam in long-term use, that is, for more than 9 weeks, has not been systematically studied in controlled clinical trials. The physician who elects to use clonazepam for extended periods should periodically reevaluate the long-term usefulness of the drug for the individual patient. Launch Date1.71071996E11 |
|||
Primary | KLONOPIN Approved UseINDICATIONS & USAGE Seizure Disorders: Clonazepam tablets, USP are useful alone or as an adjunct in the treatment of the Lennox-Gastaut syndrome (petit mal variant), akinetic and . In patients with absence seizures (petit mal) who have failed to respond to succinimides, clonazepam may be useful. In some studies, up to 30% of patients have shown a loss of anticonvulsant activity, often within 3 months of administration. In some cases, dosage adjustment may reestablish efficacy.
Panic Disorder: Clonazepam tablets, USP are indicated for the treatment of panic disorder, with or without agoraphobia, as defined in DSM-IV. Panic disorder is characterized by the occurrence of unexpected panic attacks and associated concern about having additional attacks, worry about the implications or consequences of the attacks, and/or a significant change in behavior related to the attacks. The efficacy of clonazepam was established in two 6- to 9-week trials in panic disorder patients whose diagnoses corresponded to the DSM-IIIR category of panic disorder. Panic disorder (DSM-IV) is characterized by recurrent unexpected panic attacks, ie, a discrete period of intense fear or discomfort in which four (or more) of the following symptoms develop abruptly and reach a peak within 10 minutes: (1) palpitations, pounding heart or accelerated heart rate; (2) sweating; (3) trembling or shaking; (4) sensations of shortness of breath or smothering; (5) feeling of choking; (6) chest pain or discomfort; (7) nausea or abdominal distress; (8) feeling dizzy, unsteady, lightheaded or faint; (9) derealization (feelings of unreality) or depersonalization (being detached from oneself); (10) fear of losing control; (11) fear of dying; (12) paresthesias (numbness or tingling sensations); (13) chills or hot flushes. The effectiveness of clonazepam in long-term use, that is, for more than 9 weeks, has not been systematically studied in controlled clinical trials. The physician who elects to use clonazepam for extended periods should periodically reevaluate the long-term usefulness of the drug for the individual patient. Launch Date1.71071996E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.3 ng/mL |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLONAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3 ng/mL |
0.5 mg 3 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CLONAZEPAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
102 ng × h/mL |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLONAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
339 ng × h/mL |
0.5 mg 3 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CLONAZEPAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40 h |
0.5 mg 3 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CLONAZEPAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15% |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLONAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 mg single, intramuscular Dose: 2 mg Route: intramuscular Route: single Dose: 2 mg Sources: |
healthy, 30 years (range: 23–50 years) n = 12 Health Status: healthy Age Group: 30 years (range: 23–50 years) Sex: M+F Population Size: 12 Sources: |
|
2 mg single, intravenous Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: |
healthy, 30 years (range: 23–50 years) n = 12 Health Status: healthy Age Group: 30 years (range: 23–50 years) Sex: M+F Population Size: 12 Sources: |
|
2 mg single, oral |
healthy, 30 years (range: 23–50 years) n = 12 Health Status: healthy Age Group: 30 years (range: 23–50 years) Sex: M+F Population Size: 12 Sources: |
|
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Disc. AE: Somnolence, Depression... AEs leading to discontinuation/dose reduction: Somnolence (7%) Sources: Depression (4%) Nervousness (1%) Dizziness (1%) Ataxia (1%) Intellectual disability (1%) |
6 mg 1 times / day steady, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: steady Dose: 6 mg, 1 times / day Sources: |
unhealthy |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Ataxia | 1% Disc. AE |
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Dizziness | 1% Disc. AE |
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Intellectual disability | 1% Disc. AE |
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Nervousness | 1% Disc. AE |
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Depression | 4% Disc. AE |
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Somnolence | 7% Disc. AE |
1.5 mg 1 times / day multiple, oral Recommended Dose: 1.5 mg, 1 times / day Route: oral Route: multiple Dose: 1.5 mg, 1 times / day Sources: |
unhealthy n = 574 Health Status: unhealthy Condition: seizure disorders Population Size: 574 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
weak | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Page: 2.0 |
yes | |||
yes | yes (pharmacogenomic study) Comment: The statistical analysis displayed significant association between the patients’ CYP3A4 expression and the stable plasma concentrations of clonazepam normalized by the dose and the patient’s bodyweight. |
PubMed
Title | Date | PubMed |
---|---|---|
Letter: Clonazepam in the treatment of drug-induced dyskinesia. | 1975 Feb 1 |
|
The role of gamma-aminobutyric acid (GABA)-benzodiazepine neurotransmission in an animal model of methamphetamine-induced psychosis. | 1999 Mar |
|
Interstrain differences in cognitive functions in rats in relation to status epilepticus. | 2000 Jul |
|
Gabapentin prophylaxis of clozapine-induced seizures. | 2000 Mar |
|
Pharmacological options for the treatment of Tourette's disorder. | 2001 |
|
LSD-induced Hallucinogen Persisting Perception Disorder treated with clonazepam: two case reports. | 2001 |
|
[Clonazepam in the treatment of labile arterial hypertension in the elderly]. | 2001 |
|
[Clonazepam in therapy of neurogenic syncopal states]. | 2001 |
|
Benzodiazepines and anticonvulsants for social phobia (social anxiety disorder). | 2001 |
|
Expression of the peripheral-type benzodiazepine receptor and apoptosis induction in hepatic stellate cells. | 2001 Apr |
|
Nonconvulsive status epilepticus associated with cephalosporins in patients with renal failure. | 2001 Aug |
|
Smoking and panic disorder. | 2001 Aug |
|
Gamma irradiation effects on stability of poly(lactide-co-glycolide) microspheres containing clonazepam. | 2001 Aug 10 |
|
[Primary orthostatic tremor: slow harmonic component as responsible of inestability]. | 2001 Aug-Sep |
|
Pharmacoepidemiologic investigation of a clonazepam-carbamazepine interaction by mixed effect modeling using routine clinical pharmacokinetic data in Japanese patients. | 2001 Dec |
|
Pharmacological characterization of the 6 Hz psychomotor seizure model of partial epilepsy. | 2001 Dec |
|
Direct LC analysis of five benzodiazepines in human urine and plasma using an ADS restricted access extraction column. | 2001 Dec |
|
Roles for mitochondrial and reverse mode Na+/Ca2+ exchange and the plasmalemma Ca2+ ATPase in post-tetanic potentiation at crayfish neuromuscular junctions. | 2001 Dec 15 |
|
Sleep disorders. | 2001 Feb |
|
Focal stiff-person syndrome. | 2001 Feb |
|
Results of intensive chemotherapy followed by hematopoietic stem-cell rescue in 22 patients with refractory or recurrent primary CNS lymphoma or intraocular lymphoma. | 2001 Feb 1 |
|
[Antiepileptic drugs and neuropathic pain]. | 2001 Feb 16-28 |
|
Evaluation of native GABA(A) receptors containing an alpha 5 subunit. | 2001 Feb 9 |
|
Treatment of bipolar depression with twice-weekly fluoxetine: management of antidepressant-induced mania. | 2001 Jan |
|
Infantile status epilepticus in Tunisia. Clinical, etiological and prognostic aspects. | 2001 Jul |
|
[Piracetam in the treatment of a patient with idiopathic cortical myoclonus]. | 2001 Jul 16-31 |
|
Burning mouth syndrome after taking clonazepam. | 2001 Jul-Aug |
|
Peripheral-type benzodiazepine receptor ligands: mitochondrial permeability transition induction in rat cardiac tissue. | 2001 Mar 15 |
|
Interaction of GYKI 52466, a selective non-competitive antagonist of AMPA/kainate receptors, with conventional antiepileptic drugs in amygdala-kindled seizures in rats. | 2001 Mar-Apr |
|
[3H]Flunitrazepam binding to recombinant alpha1beta2gamma2S GABAA receptors stably expressed in HEK 293 cells. | 2001 May |
|
Behavioral effects of agents active at the gamma-aminobutyric acid receptor complex in the staircase paradigm. | 2001 May 18 |
|
Obstetrical and neonatal outcome following clonazepam use during pregnancy: a case series. | 2001 May-Jun |
|
Stiff leg syndrome: case report. | 2001 Nov |
|
Fast orthostatic tremor in Parkinson's disease mimicking primary orthostatic tremor. | 2001 Nov |
|
Selective, high-resolution fluorescence imaging of mitochondrial Ca2+ concentration. | 2001 Nov |
|
West syndrome: the Philippine experience. | 2001 Nov |
|
Kinetic and pharmacological properties of GABA(A) receptors in single thalamic neurons and GABA(A) subunit expression. | 2001 Nov |
|
Increased [Mg2+]o reduces Ca2+ influx and disruption of mitochondrial membrane potential during reoxygenation. | 2001 Nov |
|
Successful use of methadone in the treatment of chronic neuropathic pain arising from burn injuries: a case-study. | 2001 Nov |
|
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column. | 2001 Nov 15 |
|
Population pharmacokinetic analysis resulting in a tool for dose individualization of busulphan in bone marrow transplantation recipients. | 2001 Oct |
|
Influence of age and comedication on steady-state clonazepam serum level-dose ratios in Japanese epileptic patients. | 2001 Oct |
|
2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands. | 2001 Oct |
|
Nutritional parameters modify muricidal behavior of male Wistar rats: preventive effects of amino acids and 4' Cl diazepam. | 2001 Oct 26 |
|
Evaluation of in vitro percutaneous absorption of lorazepam and clonazepam from hydro-alcoholic gel formulations. | 2001 Oct 9 |
|
Effect of midazolam on interleukin-6 mRNA expression in human peripheral blood mononuclear cells in the absence of lipopolysaccharide. | 2001 Sep 21 |
|
[Treatment and long-term follow-up of post-anoxic myoclonus]. | 2001 Sep 23 |
|
Burning mouth syndrome. | 2001 Summer |
|
Effects of commonly used benzodiazepines on the fetus, the neonate, and the nursing infant. | 2002 Jan |
|
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine. | 2002 Jan 1 |
Patents
Sample Use Guides
Seizure Disorders: Adults: The initial dose for adults with seizure disorders should not
exceed 1.5 mg/day divided into three doses. Dosage may be increased in increments of
0.5 to 1 mg every 3 days until seizures are adequately controlled or until side effects
preclude any further increase. Maintenance dosage must be individualized for each
patient depending upon response. Maximum recommended daily dose is 20 mg. Clonazepam is available as a tablet or an orally disintegrating tablet (wafer). The tablets
should be administered with water by swallowing the tablet whole. The orally
disintegrating tablet should be administered as follows: After opening the pouch, peel
back the foil on the blister. Do not push tablet through foil. Immediately upon opening
the blister, using dry hands, remove the tablet and place it in the mouth. Tablet
disintegration occurs rapidly in saliva so it can be easily swallowed with or without water.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11698521
Clonazepam (100 nM) increased inhibitory postsynaptic current (IPSC) decay time constants in rat thalamic nuclei-the reticular nucleus (nRt) (from 44.3 to 77.9 ms, P < 0.01) but not in the ventrobasal (VB) complex..
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:21:19 UTC 2023
by
admin
on
Thu Jul 06 22:21:19 UTC 2023
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Record UNII |
5PE9FDE8GB
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Record Status |
Validated (UNII)
|
Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175694
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WHO-VATC |
QN03AE01
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NCI_THESAURUS |
C264
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FDA ORPHAN DRUG |
243507
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WHO-ATC |
N03AE01
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NDF-RT |
N0000007542
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NCI_THESAURUS |
C1012
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DEA NO. |
2737
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LIVERTOX |
NBK548030
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FDA ORPHAN DRUG |
82794
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2802
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CLONAZEPAM
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100000084528
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2598
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703
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179913
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Clonazepam
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5PE9FDE8GB
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DB01068
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1622-61-3
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D002998
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1140305
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3756
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M3649
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PRIMARY | Merck Index | ||
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216-596-2
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DTXSID1022845
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2765
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C28935
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5PE9FDE8GB
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SUB06728MIG
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CHEMBL452
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3265
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6963
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TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM) |
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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BINDING
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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Biological Half-life | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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PROTEIN BINDING | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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