Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H21N3O |
Molecular Weight | 307.3895 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C3=CC=C(C)C=C3
InChI
InChIKey=ZAFYATHCZYHLPB-UHFFFAOYSA-N
InChI=1S/C19H21N3O/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19/h5-10,12H,11H2,1-4H3
Molecular Formula | C19H21N3O |
Molecular Weight | 307.3895 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Zolpidem is usually used for the treatment of insomnia as a hypnotic drug. It was also suggested to be effective in the treatment of dystonia in some studies. Zolpidem can be one of useful alternative pharmacological treatments for blepharospasm. Zolpidem interacts with a GABA-BZ receptor complex and shares some of the pharmacological properties of the benzodiazepines. In contrast to the benzodiazepines, which non-selectively bind to and activate all BZ receptor subtypes, zolpidem in vitro binds the BZ1 receptor preferentially with a high affinity ratio of the α1/α5 subunits. This selective binding of zolpidem on the BZ1 receptor is not absolute, but it may explain the relative absence of myorelaxant and anticonvulsant effects in animal studies as well as the preservation of deep sleep in human studies of zolpidem tartrate at hypnotic doses.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22922343 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMBIEN Approved UseAmbien (zolpidem tartrate) is indicated for the short-term treatment of insomnia characterized by difficulties with sleep initiation. Ambien has been shown to decrease sleep latency for up to 35 days in controlled clinical studies [see Clinical Studies (14) Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
59 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
121 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2.5 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.5% |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
7.5% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years Health Status: unhealthy Age Group: 2 - 12 years Sex: M+F Sources: |
Other AEs: Psychiatric symptom, Gastrointestinal disorder (NOS)... Other AEs: Psychiatric symptom (6 patients) Sources: Gastrointestinal disorder (NOS) (6 patients) Nervous system disorder NOS (5 patients) |
300 mg single, oral Overdose |
unhealthy, 68 years |
Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Drowsiness, Vertigo... AEs leading to discontinuation/dose reduction: Drowsiness (1.1%) Sources: Vertigo (0.8%) Amnesia (0.5%) Nausea (0.5%) Headache (0.4%) Fall (0.4%) |
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Drowsiness, Dizziness... AEs leading to discontinuation/dose reduction: Drowsiness (0.5%) Sources: Dizziness (0.4%) Headache (0.5%) Nausea (0.6%) Vomiting (0.5%) |
600 mg single, oral Overdose |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 10 patients) Sources: |
600 mg single, oral Overdose |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Somnolence, Coma... AEs leading to discontinuation/dose reduction: Somnolence (100%) Sources: Coma (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nervous system disorder NOS | 5 patients | 0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years Health Status: unhealthy Age Group: 2 - 12 years Sex: M+F Sources: |
Gastrointestinal disorder (NOS) | 6 patients | 0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years Health Status: unhealthy Age Group: 2 - 12 years Sex: M+F Sources: |
Psychiatric symptom | 6 patients | 0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years Health Status: unhealthy Age Group: 2 - 12 years Sex: M+F Sources: |
Death | grade 5, 1 patient Disc. AE |
300 mg single, oral Overdose |
unhealthy, 68 years |
Fall | 0.4% Disc. AE |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 0.4% Disc. AE |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Amnesia | 0.5% Disc. AE |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Nausea | 0.5% Disc. AE |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Vertigo | 0.8% Disc. AE |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Drowsiness | 1.1% Disc. AE |
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dizziness | 0.4% Disc. AE |
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Drowsiness | 0.5% Disc. AE |
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 0.5% Disc. AE |
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Vomiting | 0.5% Disc. AE |
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Nausea | 0.6% Disc. AE |
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Death | grade 5, 10 patients Disc. AE |
600 mg single, oral Overdose |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Coma | 1 patient Disc. AE |
600 mg single, oral Overdose |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Somnolence | 100% Disc. AE |
600 mg single, oral Overdose |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 99 uM] | ||||
weak | ||||
weak |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | yes (co-administration study) Comment: A single-dose interaction study with zolpidem tartrate 10 mg and rifampin (CYP3A4 inducer) 600 mg at steady-state levels in female subjects showed significant reductions of the AUC (-73%), Cmax (-58%), and T1/2 (-36 %) of zolpidem together |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
|
Development and modulation of GABA(A) receptor-mediated neurotransmission in the CA1 region of prenatally protein malnourished rats. | 2001 |
|
[Zolpidem (ivadal) treatment of sleep disorders]. | 2001 |
|
Future directions in the management of insomnia. | 2001 |
|
Consequences of insomnia and its therapies. | 2001 |
|
A psychiatric perspective on insomnia. | 2001 |
|
Melatonin for preventing and treating jet lag. | 2001 |
|
Ribozyme-mediated reduction of the GABA(A) receptor alpha1 subunit. | 2001 Aug 15 |
|
Zolpidem use and hip fractures in older people. | 2001 Dec |
|
[Drug for the treatment of sleep disorders--review]. | 2001 Jan |
|
[Homeopathic specialties as substitutes for benzodiazepines: double-blind vs. placebo study]. | 2001 Jul-Aug |
|
A double-blind, randomized and placebo-controlled study on the polysomnographic withdrawal effects of zopiclone, zolpidem and triazolam in healthy subjects. | 2001 Jun |
|
gamma-Aminobutyric acid(A) receptor subunit expression predicts functional changes in hippocampal dentate granule cells during postnatal development. | 2001 Jun |
|
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus. | 2001 Mar |
|
Effect of alpha subunit on allosteric modulation of ion channel function in stably expressed human recombinant gamma-aminobutyric acid(A) receptors determined using (36)Cl ion flux. | 2001 May |
|
A double-blind comparative study of zolpidem versus zopiclone in the treatment of chronic primary insomnia. | 2001 May-Jun |
|
Toxicity of alpidem, a peripheral benzodiazepine receptor ligand, but not zolpidem, in rat hepatocytes: role of mitochondrial permeability transition and metabolic activation. | 2001 Nov |
|
Prevalence between different alpha subunits performing the benzodiazepine binding sites in native heterologous GABA(A) receptors containing the alpha2 subunit. | 2001 Oct |
|
Insomnia: therapeutic approach. | 2001 Sep |
|
Potency of positive gamma-aminobutyric acid(A) modulators to substitute for a midazolam discriminative stimulus in untreated monkeys does not predict potency to attenuate a flumazenil discriminative stimulus in diazepam-treated monkeys. | 2001 Sep |
|
Zolpidem in restless legs syndrome. | 2002 |
|
Tolerability of hypnosedatives in older patients. | 2002 |
|
Hallucinations and Zolpidem. | 2002 Aug |
|
Severe impairment of NMDA receptor function in mice carrying targeted point mutations in the glycine binding site results in drug-resistant nonhabituating hyperactivity. | 2002 Aug 1 |
|
The heterogeneity of central benzodiazepine receptor subtypes in the human hippocampal formation, frontal cortex and cerebellum using [3H]flumazenil and zolpidem. | 2002 Aug 15 |
|
[Pharmacological profile and clinical effect of zolpidem (Myslee tablets), a hypnotic agent]. | 2002 Feb |
|
Mechanism of alpha-subunit selectivity of benzodiazepine pharmacology at gamma-aminobutyric acid type A receptors. | 2002 Feb 15 |
|
Zolpidem improves dystonia in "Lubag" or X-linked dystonia-parkinsonism syndrome. | 2002 Feb 26 |
|
Fibromyalgia: patient perspectives on symptoms, symptom management, and provider utilization. | 2002 Jan |
|
Comparative meta-analysis of pharmacotherapy and behavior therapy for persistent insomnia. | 2002 Jan |
|
Imaging the GABA-benzodiazepine receptor subtype containing the alpha5-subunit in vivo with [11C]Ro15 4513 positron emission tomography. | 2002 Jul |
|
[Abuse, tolerance and dependence of zolpidem: three case reports]. | 2002 Jul-Aug |
|
Zolpidem, vascular headache, and hallucinations in an adolescent. | 2002 Jun |
|
Soyka M, Bottlender R, Möller H-J; Epidemiological evidence for a low abuse potential of zolpidem; Pharmacopsychiatry 2000, 33: 138 - 141. | 2002 Mar |
|
Selective actions on sleep or anxiety by exploiting GABA-A/benzodiazepine receptor subtypes. | 2002 Mar |
|
Zolpidem in progressive supranuclear palsy. | 2002 Mar |
|
Sleep disorders and daytime sleepiness in state police shiftworkers. | 2002 Mar-Apr |
|
Clinical syndrome associated with zolpidem ingestion in dogs: 33 cases (January 1998-July 2000). | 2002 Mar-Apr |
|
Anxiolytic-like effects of acute and chronic GABA transporter inhibition in rats. | 2002 May |
|
Selective modulation of tonic and phasic inhibitions in dentate gyrus granule cells. | 2002 May |
|
GABAA-benzodiazepine receptor complex ligands and stress-induced hyperthermia in singly housed mice. | 2002 May |
|
Rifampin and rifabutin drug interactions: an update. | 2002 May 13 |
|
Long term benzodiazepine use for insomnia in patients over the age of 60: discordance of patient and physician perceptions. | 2002 May 8 |
|
Relation between discriminative and reinforcing effects of midazolam, pentobarbital, chlordiazepoxide, zolpidem, and imidazenil in baboons. | 2002 Oct |
|
Functional characterization of GABA(A) receptors in neonatal hypothalamic brain slice. | 2002 Oct |
|
Zolpidem pharmacokinetic properties in young females: influence of smoking and oral contraceptive use. | 2002 Oct |
|
Relative picrotoxin insensitivity distinguishes ionotropic GABA receptor-mediated IPSCs in hippocampal interneurons. | 2002 Sep |
|
GABA(A) receptor alpha-1 subunit deletion alters receptor subtype assembly, pharmacological and behavioral responses to benzodiazepines and zolpidem. | 2002 Sep |
|
Mechanisms of anabolic androgenic steroid modulation of alpha(1)beta(3)gamma(2L) GABA(A) receptors. | 2002 Sep |
|
Comparison of the effects of zaleplon, zolpidem, and triazolam at various GABA(A) receptor subtypes. | 2002 Sep 13 |
Patents
Sample Use Guides
Dosage in Adults: the recommended initial dose is 5 mg for women and either 5 or 10 mg for men, taken only once per night immediately before bedtime with at least 7-8 hours remaining before the planned time of awakening. If the 5 mg dose is not effective, the dose can be increased to 10 mg. In some patients, the higher morning blood levels following use of the 10 mg dose increase the risk of next day impairment of driving and other activities that require full alertness. The total dose of AMBIEN (zolpidem tartrate) should not exceed 10 mg once daily immediately before bedtime. Ambien should be taken as a single dose and should not be readministered during the same night.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22922343
Human embryonic kidney (HEK) 293 cells stably expressing recombinant α1β2γ2s GABA(A) receptors were exposed to zolpidem (1 and 10 μmol/L) for short-term (2 h daily for 1, 2, or 3 consecutive days) or long-term (continuously for 48 h). Radioligand binding studies were used to determine the parameters of [(3)H]flunitrazepam binding sites. A single (2 h) or repeated (2 h daily for 2 or 3 d) short-term exposure to zolpidem affected neither the maximum number of [(3)H]flunitrazepam binding sites nor the affinity. In both control and short-term zolpidem treated groups, addition of GABA (1 nmol/L-1 mmol/L) enhanced [(3)H]flunitrazepam binding in a concentration-dependent manner. The maximum enhancement of [(3)H]flunitrazepam binding in short-term zolpidem treated group was not significantly different from that in the control group. In contrast, long-term exposure to zolpidem resulted in significantly increase in the maximum number of [(3)H]flunitrazepam binding sites without changing the affinity. Furthermore, long-term exposure to zolpidem significantly decreased the ability of GABA to stimulate [(3)H]flunitrazepam binding.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:07:37 GMT 2025
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on
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Record UNII |
7K383OQI23
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QN05CF02
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NDF-RT |
N0000175759
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DEA NO. |
2783
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WHO-ATC |
N05CF02
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NCI_THESAURUS |
C29756
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LIVERTOX |
NBK547962
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ZOLPIDEM
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m11661
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N0000007570
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PRIMARY | Pyridines [Chemical/Ingredient] | ||
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C62000
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TRANSPORTER -> NON-INHIBITOR |
IC50
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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METABOLITE -> 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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Route of Elimination | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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ORAL SPRAY, SL TABLET |
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Route of Elimination | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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SPECIAL POPULATIONS PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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SPECIAL POPULATIONS PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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