Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H28N2O4.ClH |
Molecular Weight | 372.887 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1
InChI
InChIKey=KTUFKADDDORSSI-UHFFFAOYSA-N
InChI=1S/C18H28N2O4.ClH/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);1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H28N2O4 |
Molecular Weight | 336.4259 |
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 |
|||
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 |
|
Autoantibodies associated with lupus induced by diverse drugs target a similar epitope in the (H2A-H2B)-DNA complex. | 1992 Jul |
|
Acebutolol-induced ventricular tachycardia reversed with sodium bicarbonate. | 1999 |
|
[The comparison of clinical effectiveness of perindopril and acebutolol in the primary hypertension treatment]. | 2001 |
|
Cardioselective beta-blocker use in patients with reversible airway disease. | 2001 |
|
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 |
|
First derivative spectrophotometric, TLC-densitometric, and HPLC determination of acebutolol HCL in presence of its acid-induced degradation product. | 2001 Feb |
|
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 |
|
Influence of carvedilol on the benefits of physical training in patients with moderate chronic heart failure. | 2001 Jun |
|
Effect of an alpha-blocker (Nicergoline) and of a beta-blocker (Acebutolol) on the in vitro biosynthesis of vascular extracellular matrix. | 2001 May |
|
[Interaction between melilot and acenocoumarol? (Melilotruscus aculeatus)]. | 2001 May-Jun |
|
beta-Adrenoceptor blockade enhances the anticonvulsant effect of glutamate receptor antagonists against maximal electroshock. | 2001 Nov 16 |
|
beta(1)-adrenergic antagonists improve sleep and behavioural disturbances in a circadian disorder, Smith-Magenis syndrome. | 2001 Sep |
|
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 |
|
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 |
|
Propranolol and metoprolol enhance the anticonvulsant action of valproate and diazepam against maximal electroshock. | 2002 Jan-Feb |
|
[Acute poisoning with nifedipine and acebutol: two cases]. | 2003 |
|
Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers. | 2003 Aug |
|
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
|
Evaluation of an immortalized retinal endothelial cell line as an in vitro model for drug transport studies across the blood-retinal barrier. | 2003 Sep |
|
Isotachophoresis of beta-blockers in a capillary and on a poly(methyl methacrylate) chip. | 2004 Jun |
|
Assay of acebutolol in pharmaceuticals by analytical capillary isotachophoresis. | 2005 Jul 15 |
|
Smith-Magenis syndrome: a case report of improved sleep after treatment with beta1-adrenergic antagonists and melatonin. | 2006 Sep |
|
[Interrelationship between changes of rate and variability of cardiac rhythm under influence of beta-adrenoblockers]. | 2007 |
|
Evaluation of chromatographic descriptors for the prediction of gastro-intestinal absorption of drugs. | 2007 Jan 5 |
|
Comparison of the analysis of beta-blockers by different techniques. | 2009 Dec 1 |
|
Determination of selected beta-receptor antagonists in biological samples by solid-phase extraction with cholesterolic phase and LC/MS. | 2009 Jan |
|
Beta-blocking agent for treatment of infantile hemangioma. | 2009 Jun |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
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
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on
Edited
Wed Jul 05 23:06:29 UTC 2023
by
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Record UNII |
B025Y34C54
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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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NCI_THESAURUS |
C29576
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EU-Orphan Drug |
EU/3/16/1742
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251-980-3
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36816
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100000091380
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DTXSID5045461
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CHEMBL642
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142130
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C28806
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6524
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2380
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B025Y34C54
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DBSALT000192
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1000601
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34381-68-5
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757412
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B025Y34C54
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SUB00240MIG
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M1290
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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RACEMATE -> ENANTIOMER | |||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |