Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H28N2O4 |
Molecular Weight | 336.4266 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC(=Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)C)O)O
InChI
InChIKey=GOEMGAFJFRBGGG-UHFFFAOYSA-N
InChI=1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)
Molecular Formula | C18H28N2O4 |
Molecular Weight | 336.4266 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Acebutolol is a cardioselective, beta-adrenoreceptor blocking agent, which possesses mild intrinsic sympathomimetic activity (ISA) in its therapeutically effective dose range. Acebutolol is marketed under the trade names Sectral, Prent. Acebutolol is indicated for the management of hypertension in adults. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. Acebutolol is also indicated in the management of ventricular premature beats; it reduces the total number of premature beats, as well as the number of paired and multiform ventricular ectopic beats, and R-on-T beats. Acebutolol is a selective β1-receptor antagonist. Activation of β1-receptors by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Acebutolol blocks these receptors, lowering the heart rate and blood pressure. This drug then has the reverse effect of epinephrine. In addition, beta blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2859774
Curator's Comment:: Acebutolol is relatively hydrophilic and does not readily cross the blood-brain barrier, a fact that may be clinically significant in reducing the frequency and severity of central nervous system adverse effects.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
741.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SECTRAL Approved UseINDICATIONS & USAGE HYPERTENSION: Acebutolol hydrochloride capsules are indicated for the management of hypertension in adults. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. VENTRICULAR ARRHYTHMIAS: Acebutolol hydrochloride capsules are indicated in the management of ventricular premature beats; it reduces the total number of premature beats, as well as the number of paired and multiform ventricular ectopic beats, and R-on-T beats. Launch Date4.73039995E11 |
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Primary | SECTRAL Approved UseINDICATIONS & USAGE HYPERTENSION: Acebutolol hydrochloride capsules are indicated for the management of hypertension in adults. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. VENTRICULAR ARRHYTHMIAS: Acebutolol hydrochloride capsules are indicated in the management of ventricular premature beats; it reduces the total number of premature beats, as well as the number of paired and multiform ventricular ectopic beats, and R-on-T beats. Launch Date4.73039995E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
92 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6884417/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEBUTOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4492 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6884417/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACEBUTOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4 h |
unknown, oral |
ACEBUTOLOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
74% |
unknown, oral |
ACEBUTOLOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
Other AEs: Breathing shallow, Nausea... Other AEs: Breathing shallow Sources: Nausea Pulse thready Tachycardia Bradycardia Asystole Death (grade 5) Blood pressure low |
9.2 g 1 times / day single, oral Overdose Dose: 9.2 g, 1 times / day Route: oral Route: single Dose: 9.2 g, 1 times / day Sources: |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
Other AEs: Blood pressure low, Heart rate low... Other AEs: Blood pressure low Sources: Heart rate low Necrosis bowel Muscle tone flaccid |
0.8 g 2 times / day multiple, oral Highest studied dose Dose: 0.8 g, 2 times / day Route: oral Route: multiple Dose: 0.8 g, 2 times / day Sources: |
unhealthy, 31-63 n = 11 Health Status: unhealthy Condition: hypertension Age Group: 31-63 Sex: M+F Population Size: 11 Sources: |
Disc. AE: Antinuclear antibody... AEs leading to discontinuation/dose reduction: Antinuclear antibody (3 patients) Sources: |
4 g 1 times / day single, oral Overdose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: |
healthy, 43 n = 1 Health Status: healthy Age Group: 43 Sex: F Population Size: 1 Sources: |
Other AEs: Blood pressure low, Ventricular tachycardia... Other AEs: Blood pressure low Sources: Ventricular tachycardia Death (grade 5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Asystole | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Blood pressure low | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Bradycardia | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Breathing shallow | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Nausea | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Pulse thready | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Tachycardia | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
|
Death | grade 5 | 6 g 1 times / day single, oral Overdose Dose: 6 g, 1 times / day Route: oral Route: single Dose: 6 g, 1 times / day Sources: |
healthy, 16 n = 1 Health Status: healthy Age Group: 16 Sex: F Population Size: 1 Sources: |
Blood pressure low | 9.2 g 1 times / day single, oral Overdose Dose: 9.2 g, 1 times / day Route: oral Route: single Dose: 9.2 g, 1 times / day Sources: |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
|
Heart rate low | 9.2 g 1 times / day single, oral Overdose Dose: 9.2 g, 1 times / day Route: oral Route: single Dose: 9.2 g, 1 times / day Sources: |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
|
Muscle tone flaccid | 9.2 g 1 times / day single, oral Overdose Dose: 9.2 g, 1 times / day Route: oral Route: single Dose: 9.2 g, 1 times / day Sources: |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
|
Necrosis bowel | 9.2 g 1 times / day single, oral Overdose Dose: 9.2 g, 1 times / day Route: oral Route: single Dose: 9.2 g, 1 times / day Sources: |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
|
Antinuclear antibody | 3 patients Disc. AE |
0.8 g 2 times / day multiple, oral Highest studied dose Dose: 0.8 g, 2 times / day Route: oral Route: multiple Dose: 0.8 g, 2 times / day Sources: |
unhealthy, 31-63 n = 11 Health Status: unhealthy Condition: hypertension Age Group: 31-63 Sex: M+F Population Size: 11 Sources: |
Blood pressure low | 4 g 1 times / day single, oral Overdose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: |
healthy, 43 n = 1 Health Status: healthy Age Group: 43 Sex: F Population Size: 1 Sources: |
|
Ventricular tachycardia | 4 g 1 times / day single, oral Overdose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: |
healthy, 43 n = 1 Health Status: healthy Age Group: 43 Sex: F Population Size: 1 Sources: |
|
Death | grade 5 | 4 g 1 times / day single, oral Overdose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: |
healthy, 43 n = 1 Health Status: healthy Age Group: 43 Sex: F Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[Pharmacology of acebutolol in animals]. | 1975 Dec 31 |
|
Acebutolol-induced ventricular tachycardia reversed with sodium bicarbonate. | 1999 |
|
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites. | 2000 Apr |
|
Evidence towards the role of arylamine N-acetyltransferase in Mycobacterium smegmatis and development of a specific antiserum against the homologous enzyme of Mycobacterium tuberculosis. | 2001 Dec |
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Comparison of the effect of perindopril and acebutolol on cerebral hemodynamics in hypertensive patients. | 2001 Jan |
|
Effect of lipophilicity on in vivo iontophoretic delivery. II. Beta-blockers. | 2001 Jun |
|
Cardioselective beta-blockers for reversible airway disease. | 2002 |
|
Pharmacokinetics of acebutolol and its main metabolite, diacetolol after oral administration of acebutolol in rabbits with carbon tetrachloride-induced hepatic failure. | 2002 Aug |
|
Beta-adrenergic blockade during severe ischemia. | 2002 Dec |
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Beta-adrenergic-receptor blockade and myocardial ischemia: something old, something new. | 2002 Dec |
|
The effect of selective beta1-blockade on EMG signal characteristics during progressive endurance exercise. | 2002 Dec |
|
Electrocardiographic changes associated with beta-blocker toxicity. | 2002 Dec |
|
Screening drugs for metabolic stability using pulsed ultrafiltration mass spectrometry. | 2002 Feb |
|
Isolation and properties of genetically defined strains of the methylotrophic yeast Hansenula polymorpha CBS4732. | 2002 Feb |
|
[Acebutolol in the treatment of arterial hypertension in pregnancy--comparison with commonly used hypertensive agents]. | 2002 Jan |
|
Mutations of muscle glycogen synthase that disable activation by glucose 6-phosphate. | 2002 Jan 15 |
|
Influence of cimetidine co-administration on the pharmacokinetics of acebutolol enantiomers and its metabolite diacetolol in a rat model: the effect of gastric pH on double-peak phenomena. | 2003 Apr 14 |
|
Changes in serum lipids and antioxidant status in west Algerian patients with essential hypertension treated with acebutolol compared to healthy subjects. | 2003 Aug |
|
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. | 2003 Aug |
|
Sleep-deprived mice show altered cytokine production manifest by perturbations in serum IL-1ra, TNFa, and IL-6 levels. | 2003 Dec |
|
Beta 1-adrenergic antagonists and melatonin reset the clock and restore sleep in a circadian disorder, Smith-Magenis syndrome. | 2003 Jan |
|
Atrial fibrillation in chronic dialysis patients in the United States: risk factors for hospitalization and mortality. | 2003 Jan 24 |
|
Pharmacokinetic changes of acebutolol after oral administration in rabbits with diabetes mellitus induced by alloxan. | 2003 Jun |
|
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor. | 2003 Jun |
|
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
|
Evaluation of teicoplanin chiral stationary phases of 3.5 and 5 microm inside diameter silica microparticles by polar-organic mode capillary electrochromatography. | 2003 Sep |
|
Nodal and BMP2/4 signaling organizes the oral-aboral axis of the sea urchin embryo. | 2004 Mar |
|
Effects of grapefruit juice on the pharmacokinetics of acebutolol. | 2005 Dec |
|
Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. | 2005 Oct |
|
Acebutolol-induced subacute cutaneous lupus erythematosus. | 2005 Sep-Oct |
|
Transport of acebutolol through rabbit corneal epithelium. | 2006 Apr |
|
UPLC/MS for the identification of beta-blockers. | 2006 Feb 24 |
|
Spectrophotometric and spectrofluorimetric methods for analysis of acyclovir and acebutolol hydrochloride. | 2006 Nov |
|
Analysis of neutral and basic pharmaceuticals in sewage treatment plants and in recipient rivers using solid phase extraction and liquid chromatography-tandem mass spectrometry detection. | 2006 Nov 17 |
|
[Interrelationship between changes of rate and variability of cardiac rhythm under influence of beta-adrenoblockers]. | 2007 |
|
Clinical review: aggressive management and extracorporeal support for drug-induced cardiotoxicity. | 2007 |
|
Antihypertensive and antioxidant action of amlodipine and vitamin C in patients of essential hypertension. | 2007 Mar |
|
Stability of chosen beta-adrenolytic drugs of different polarity in basic environment. | 2008 Mar-Apr |
|
Involvement of influx and efflux transport systems in gastrointestinal absorption of celiprolol. | 2009 Jul |
|
Application of ionic liquids in high performance reversed-phase chromatography. | 2009 Jun 4 |
|
[Beta blockers in migraine prophylaxis]. | 2009 Oct |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Medicinal chemistry of drugs used in diabetic cardiomyopathy. | 2010 |
|
Correlation effect of EGFR and CXCR4 and CCR7 chemokine receptors in predicting breast cancer metastasis and prognosis. | 2010 Feb 24 |
|
Principal component analysis of HPLC retention data and molecular modeling structural parameters of cardiovascular system drugs in view of their pharmacological activity. | 2010 Jul 9 |
|
Occurrence and removal of estrogens and beta blockers by various processes in wastewater treatment plants. | 2010 Sep 1 |
Sample Use Guides
Hypertension
The initial dosage of acebutolol in uncomplicated mild-to-moderate hypertension is 400 mg. This can be given as a single daily dose, but in occasional patients twice daily dosing may be required for adequate 24-hour blood-pressure control. An optimal response is usually achieved with dosages of 400 to 800 mg per day, although some patients have been maintained on as little as 200 mg per day. Patients with more severe hypertension or who have demonstrated inadequate control may respond to a total of 1200 mg daily (administered b.i.d.), or to the addition of a second antihypertensive agent. Beta-1 selectivity diminishes as dosage is increased.
Ventricular Arrhythmia
The usual initial dose of acebutolol is 400 mg daily given as 200 mg b.i.d. Dosage should be increased gradually until an optimal clinical response is obtained, generally at 600 to 1200 mg per day. If treatment is to be discontinued, the dosage should be reduced gradually over a period of about two weeks.
Use in Older Patients
Older patients have an approximately 2-fold increase in bioavailability and may require lower maintenance doses. Doses above 800 mg/day should be avoided in the elderly.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6115715
Two adrenergic receptor antagonists, acebutolol and propranolol, were observed to depress rabbit heart contractile force and adrenaline-stimulated adenylate cyclase activity at 1 X 10-(5) to 1 X 10-(3) M and 1 X 10-(6) to 1 X 10-(3) M concentrations, respectively. Acebutolol depressed sarcoplasmic reticular and mitochondrial calcium uptake at 5 X 10-(3) to 10-(2) M concentrations.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 12:36:14 UTC 2021
by
admin
on
Sat Jun 26 12:36:14 UTC 2021
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Record UNII |
67P356D8GH
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
C07AB04
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NDF-RT |
N0000175556
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NDF-RT |
N0000000161
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WHO-VATC |
QC07AB04
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LIVERTOX |
7
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WHO-ATC |
C07BB04
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NCI_THESAURUS |
C29576
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3295
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D000070
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C61525
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1978
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253-539-0
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DB01193
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149
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SUB07371MIG
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M1290
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Acebutolol
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67P356D8GH
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37517-30-9
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37517-30-9
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CHEMBL642
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40
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ACEBUTOLOL
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7107
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
SHORT-ACTING
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE ACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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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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