Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H13N |
Molecular Weight | 135.2066 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(Cc1ccccc1)N
InChI
InChIKey=KWTSXDURSIMDCE-UHFFFAOYSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
Molecular Formula | C9H13N |
Molecular Weight | 135.2066 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment:: description was created based on several sources, including
https://www.caremark.com/portal/asset/FEP_Rationale_Amphetamine.pdf
https://www.ncbi.nlm.nih.gov/pubmed/23539642
http://www.cesar.umd.edu/cesar/drugs/amphetamines.asp
Curator's Comment:: description was created based on several sources, including
https://www.caremark.com/portal/asset/FEP_Rationale_Amphetamine.pdf
https://www.ncbi.nlm.nih.gov/pubmed/23539642
http://www.cesar.umd.edu/cesar/drugs/amphetamines.asp
Amphetamine is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. The mode of therapeutic action in ADHD is not known. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT. Several currently prescribed amphetamine formulations contain both enantiomers, including Adderall, Dyanavel XR, and Evekeo, the last of which is racemic amphetamine sulfate. Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine.
CNS Activity
Sources: https://nootropicscity.com/comprehensive-write-amphetamines-adderall-ritalin-vyvanse-concerta/
Curator's Comment:: Amphetamines readily cross the blood-brain barrier to reach their primary sites of action in the brain. The acute administration of amphetamine produces a wide range of dose-dependent behavioral changes, including increased arousal or wakefulness, anorexia, hyperactivity, perseverative movements, and, in particular, a state of pleasurable affect, elation, and euphoria, which can lead to the abuse of the drug.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7751968 |
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Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=15602501 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DYANAVEL XR Approved UseINDICATIONS Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and Narcolepsy. Attention Deficit Hyperactivity Disorder (ADHD) A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV®) implies the presence of hyperactive-impulsive or inattentive symptoms that caused impairment and were present before age 7 years. The symptoms must cause clinically significant impairment, e.g., in social, academic, or occupational functioning, and be present in two or more settings, e.g., school (or work) and at home. The symptoms must not be better accounted for by another mental disorder. For the Inattentive Type, at least six of the following symptoms must have persisted for at least 6 months: lack of attention to details/careless mistakes; lack of sustained attention; poor listener; failure to follow through on tasks; poor organization; avoids tasks requiring sustained mental effort; loses things; easily distracted; forgetful. For the Hyperactive-Impulsive Type, at least six of the following symptoms must have persisted for at least 6 months: fidgeting/squirming; leaving seat; inappropriate running/climbing; difficulty with quiet activities; “on the go;” excessive talking; blurting answers; can't wait turn; intrusive. The Combined Type requires both inattentive and hyperactive-impulsive criteria to be met. Special Diagnostic Considerations: Specific etiology of this syndrome is unknown, and there is no single diagnostic test. Adequate diagnosis requires the use not only of medical but of special psychological, educational, and social resources. Learning may or may not be impaired. The diagnosis must be based upon a complete history and evaluation of the child and not solely on the presence of the required number of DSM-IV® characteristics. Need for Comprehensive Treatment Program: Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets is indicated as an integral part of a total treatment program for ADHD that may include other measures (psychological, educational, social) for patients with this syndrome. Drug treatment may not be indicated for all children with this syndrome. Stimulants are not intended for use in the child who exhibits symptoms secondary to environmental factors and/or other primary psychiatric disorders, including psychosis. Appropriate educational placement is essential and psychosocial intervention is often helpful. When remedial measures alone are insufficient, the decision to prescribe stimulant medication will depend upon the physician's assessment of the chronicity and severity of the child's symptoms. Long-Term Use: The effectiveness of Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets for long-term use has not been systematically evaluated in controlled trials. Therefore, the physician who elects to use Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets for extended periods should periodically re-evaluate the long-term usefulness of the drug for the individual patient. Launch Date1.44521285E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
120 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1727 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
Title | Date | PubMed |
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Acute subarachnoid hemorrhage. | 1975 Jul 7 |
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[Amphetamine-induced psychosis]. | 1998 |
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Behavioral studies of the effects of moderate oligemic hypoxia caused by bilateral clamping of carotid arteries in mice. Impairment of spatial working memory. | 1998 Jul-Oct |
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[Intracerebral hemorrhage following amphetamine use]. | 1998 Nov-Dec |
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The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved? | 1999 |
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HPLC with fluorescence detection of methamphetamine and amphetamine in segmentally analyzed human hair. | 1999 Apr |
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Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice. | 1999 Aug |
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Cocaine-seeking produced by experimenter-administered drug injections: dose-effect relationships in rats. | 1999 Dec |
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Enantiomer-specific high-performance liquid chromatography with fluorescence detection of methamphetamines in abusers' hair and urine. | 1999 Dec |
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The promotion effect of anorectic drugs on aflatoxin B(1)-induced hepatic preneoplastic foci. | 1999 Sep |
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Differential regulation of calmodulin content and calmodulin messenger RNA levels by acute and repeated, intermittent amphetamine in dopaminergic terminal and midbrain areas. | 2000 |
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Profiles of cognitive dysfunction in chronic amphetamine and heroin abusers. | 2000 Aug |
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[Fatal intracerebral hemorrhage after amphetamine intake]. | 2000 Jul 31 |
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Effect of dopamine agonists and antagonists on the lorazepam withdrawal syndrome in rats. | 2000 Mar |
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Effects of repeated withdrawal from continuous amphetamine administration on brain reward function in rats. | 2000 Nov |
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Evaluation of the alpha2C-adrenoceptor as a neuropsychiatric drug target studies in transgenic mouse models. | 2001 Apr 6 |
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Attention-deficit/hyperactivity disorder in adults: beyond controversy. | 2001 Aug |
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Developmental aspects of psychostimulant treatment in children and adolescents with attention-deficit/hyperactivity disorder. | 2001 Dec |
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Role of hypothalamic neuropeptide Y (NPY) in the change of feeding behavior induced by repeated treatment of amphetamine. | 2001 Dec 7 |
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Placebo-controlled evaluation of amphetamine mixture-dextroamphetamine salts and amphetamine salts (Adderall): efficacy rate and side effects. | 2001 Jan |
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Behavioural and anti-psychotic effects of Ca2+ channel blockers in rhesus monkey. | 2001 Jan 26 |
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Effects of drugs of abuse on response accuracy and bias under a delayed matching-to-sample procedure in squirrel monkeys. | 2001 Jul |
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Adderall and the FDA. | 2001 Jul |
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Acute myocardial infarction caused by amphetamines: a case report and review of the literature. | 2001 Jun |
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Short-term cardiovascular effects of methylphenidate and adderall. | 2001 May |
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Cholecystokinin2 receptor-deficient mice display altered function of brain dopaminergic system. | 2001 Nov |
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Double-blind, placebo-controlled study of single-dose amphetamine formulations in ADHD. | 2001 Nov |
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The effects of delayed rewards, tokens, and stimulant medication on sportsmanlike behavior with ADHD-diagnosed children. | 2002 Apr |
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A randomized, double-blind, placebo-controlled, parallel-group study of SLI381 (Adderall XR) in children with attention-deficit/hyperactivity disorder. | 2002 Aug |
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Synthesis and D(2)-like binding affinity of new derivatives of N-(1-ethyl-2-pyrrolidinylmethyl)-4,5-dihydro-1H-benzo[g]indole-3-carboxamide and related 4H-[1]benzothiopyrano[4,3-b]pyrrole and 5,6-dihydro-4H-benzo[6,7]cyclohepta[b]pyrrole-3-carboxamide analogues. | 2002 Aug |
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Effects of amphetamine on the plus-maze discriminative avoidance task in mice. | 2002 Feb |
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Cocaine and amphetamine depress striatal GABAergic synaptic transmission through D2 dopamine receptors. | 2002 Feb |
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Efficacy of Adderall and methylphenidate in attention deficit hyperactivity disorder: a drug-placebo and drug-drug response curve analysis of a naturalistic study. | 2002 Jun |
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The ability of amphetamine to evoke arc (Arg 3.1) mRNA expression in the caudate, nucleus accumbens and neocortex is modulated by environmental context. | 2002 Mar 15 |
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The neurosteroid 3 alpha-hydroxy-5 alpha-pregnan-20-one affects dopamine-mediated behavior in rodents. | 2002 May |
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Spatial and temporal profile of haloperidol-induced immediate-early gene expression and phosphoCREB binding in the dorsal and ventral striatum of amphetamine-sensitized rats. | 2002 Sep 15 |
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Case series: Adderall augmentation of serotonin reuptake inhibitors in childhood-onset obsessive compulsive disorder. | 2002 Summer |
Sample Use Guides
DYANAVEL XR (R (amphetamine) extended-release oral suspension) should be orally administered once daily in the morning with or without food. The dose should be individualized according to the needs and responses of the patient. Before administering the dose, shake the bottle of DYANAVEL XR.
In children 6 years of age and older, start with 2.5 mg or 5 mg once daily in the morning. The dose may be increase
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24672014
Curator's Comment:: Amph increases the effects induced by βPEA on the LGC-55, indicating that Amph potentiates the effects generated by the biogenic amine βPEA
β-Phenylethylamine (βPEA) activates the amine-gated chloride channel LGC-55 more efficiently than amphetamine (Amph) (Km = 9 and 152 μm, respectively)
Substance Class |
Chemical
Created
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admin
on
Edited
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on
Sat Jun 26 09:16:41 UTC 2021
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Record UNII |
CK833KGX7E
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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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CFR |
21 CFR 250.101
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LIVERTOX |
50
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NDF-RT |
N0000175729
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WHO-VATC |
QN06BA01
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NCI_THESAURUS |
C47795
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DEA NO. |
1100
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WHO-ATC |
N06BA01
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CFR |
21 CFR 862.3100
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FDA ORPHAN DRUG |
405313
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DEA NO. |
7401
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NDF-RT |
N0000175739
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CFR |
21 CFR 310.502
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Code System | Code | Type | Description | ||
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C62006
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PRIMARY | |||
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195
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PRIMARY | |||
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300-62-9
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PRIMARY | |||
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300-62-9
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PRIMARY | |||
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D000661
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PRIMARY | |||
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3287
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AMPHETAMINE
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M1849
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PRIMARY | Merck Index | ||
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DB00182
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4804
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3007
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Amphetamine
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377
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SUB05418MIG
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206-096-2
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CK833KGX7E
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PA 003
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CHEMBL405
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725
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PRIMARY | RxNorm |
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST | |||
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SALT/SOLVATE -> PARENT | |||
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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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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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DERIVATIVE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE |
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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PARENT -> METABOLITE | |||
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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PARENT -> IMPURITY |
UNSPECIFIED
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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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