A cardioselective beta-adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm as well as weak inherent sympathomimetic action.

Structure

Similar Structures

Synonyms

(±)-acebutolol
3'-acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide
5'-butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone
Acebutolol
Acebutololum
Acetobutolol
N-(3-acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide
N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Acebutolol Hydrochloride	B025Y34C54	34381-68-5	KTUFKADDDORSSI-UHFFFAOYSA-N

Prescription Products

Name	Dosage	Route	Labeller	Marketing Start	Marketing End
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Acebutolol	Tablet	Oral	Sanis Health Inc	2010-02-25	2018-07-16
Acebutolol	Tablet	Oral	Sanis Health Inc	2010-02-25	2018-07-16
Acebutolol	Tablet	Oral	Sanis Health Inc	2010-02-25	2018-07-16
Acebutolol - 400	Tablet	Oral	Pro Doc Limitee	1996-12-31	Not applicable
Acebutolol-100	Tablet	Oral	Pro Doc Limitee	1996-12-31	Not applicable
Acebutolol-200	Tablet	Oral	Pro Doc Limitee	1996-12-31	Not applicable
Monitan 100	Tablet	Oral	Wyeth Ltd.	1995-12-31	2004-09-13
Monitan 200	Tablet	Oral	Wyeth Ltd.	1995-12-31	2007-01-22
Monitan 400	Tablet	Oral	Wyeth Ltd.	1994-12-31	2007-01-22
Monitan Tab 200mg	Tablet	Oral	Wyeth Ltd.	1987-12-31	1996-09-10

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Acebutolol Hydrochloride	Capsule	400 mg/1	Oral	Amneal Pharmaceuticals LLC	2009-12-01	Not applicable
Acebutolol Hydrochloride	Capsule	400 mg/1	Oral	Physicians Total Care, Inc.	2005-04-22	Not applicable
Acebutolol Hydrochloride	Capsule	200 mg/1	Oral	AvPAK	2010-09-16	Not applicable
Acebutolol Hydrochloride	Capsule	400 mg/1	Oral	Mylan Pharmaceuticals Inc.	1995-04-24	Not applicable
Acebutolol Hydrochloride	Capsule	200 mg/1	Oral	Amneal Pharmaceuticals LLC	2009-12-01	Not applicable
Acebutolol Hydrochloride	Capsule	200 mg/1	Oral	Physicians Total Care, Inc.	2006-02-01	2012-06-30
Acebutolol Hydrochloride	Capsule	200 mg/1	Oral	bryant ranch prepack	2009-12-01	2010-06-01
Acebutolol Hydrochloride	Capsule	200 mg/1	Oral	Mylan Pharmaceuticals Inc.	1995-04-24	Not applicable
Acebutolol Hydrochloride	Capsule	400 mg/1	Oral	Amneal Pharmaceuticals of New York Llc	2009-12-01	Not applicable
Acebutolol Hydrochloride	Capsule	200 mg/1	Oral	Major	2009-12-01	2018-09-13

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands

Prent (Bayer)

Categories

UNII

67P356D8GH

CAS number

37517-30-9

Weight

Average: 336.4259
Monoisotopic: 336.204907394

Chemical Formula

C₁₈H₂₈N₂O₄

InChI Key

GOEMGAFJFRBGGG-UHFFFAOYSA-N

InChI

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)

IUPAC Name

N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide

SMILES

CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1

Pharmacology

Indication

For the management of hypertension and ventricular premature beats in adults.

Associated Conditions

Pharmacodynamics

Acebutolol is a cardioselective, beta-adrenoreceptor blocking agent, which possesses mild intrinsic sympathomimetic activity (ISA) in its therapeutically effective dose range. In general, beta-blockers reduce the work the heart has to do and allow it to beat more regularly. Acebutolol has less antagonistic effects on peripheral vascular ß2-receptors at rest and after epinephrine stimulation than nonselective beta-antagonists. Low doses of acebutolol produce less evidence of bronchoconstriction than nonselective agents like propranolol but more than atenolol.

Mechanism of action

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.

Target	Actions	Organism
ABeta-1 adrenergic receptor	partial agonist	Humans
UBeta-2 adrenergic receptor	partial agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Well absorbed from the Gl tract with an absolute bioavailability of approximately 40% for the parent compound. In

Volume of distribution

Not Available

Protein binding

26%

Metabolism

Subject to extensive first-pass hepatic biotransformation (primarily to diacetolol).

Route of elimination

Elimination via renal excretion is approximately 30% to 40% and by non-renal mechanisms 50% to 60%, which includes excretion into the bile and direct passage through the intestinal wall.

Half life

The plasma elimination half-life is approximately 3 to 4 hours. The half-life of its metabolite, diacetolol, is 8 to 13 hours.

Clearance

Not Available

Toxicity

Symptoms of overdose include extreme bradycardia, advanced atrioventricular block, intraventricular conduction defects, hypotension, severe congestive heart failure, seizures, and in susceptible patients, bronchospasm, and hypoglycemia.

Affected organisms

Humans and other mammals

Pathways

Pathway	Category
Acebutolol Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Unlock Additional Data
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine	The metabolism of Acebutolol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Acebutolol.
1-benzylimidazole	1-benzylimidazole may decrease the antihypertensive activities of Acebutolol.
1,10-Phenanthroline	1,10-Phenanthroline may increase the bradycardic activities of Acebutolol.
2,4-thiazolidinedione	The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Acebutolol.
2,5-Dimethoxy-4-ethylamphetamine	The therapeutic efficacy of Acebutolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The therapeutic efficacy of Acebutolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
25-desacetylrifapentine	The metabolism of Acebutolol can be increased when combined with 25-desacetylrifapentine.
3-isobutyl-1-methyl-7H-xanthine	The risk or severity of adverse effects can be increased when Acebutolol is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acid	The risk or severity of adverse effects can be increased when Acebutolol is combined with 3,5-diiodothyropropionic acid.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Take without regard to meals; absorption rate and maximal concentration are slightly reduced but the extent of absorption is not affected.

References

Synthesis Reference

US3857952

General References

Not Available

External Links

Human Metabolome Database: HMDB0015324
KEGG Drug: D02338
KEGG Compound: C06803
PubChem Compound: 1978
PubChem Substance: 46509113
ChemSpider: 1901
BindingDB: 25755
ChEBI: 2379
ChEMBL: CHEMBL642
Therapeutic Targets Database: DAP000484
PharmGKB: PA448011
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Acebutolol

ATC Codes

C07AB04 — Acebutolol

C07BB04 — Acebutolol and thiazides

AHFS Codes

24:24.00 — Beta-adrenergic Blocking Agents

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Completed	Treatment	Cardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases	1
3	Terminated	Treatment	Hemangiomas	1
4	Completed	Treatment	Healthy Volunteers	1
Not Available	Completed	Treatment	Arrhythmia / Atrial Fibrillation (AF)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Alphapharm Party Ltd.
Amneal Pharmaceuticals
Bryant Ranch Prepack
Caremark LLC
Kaiser Foundation Hospital
Major Pharmaceuticals
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Patheon Inc.
Pharmaceutical Utilization Management Program VA Inc.
Physicians Total Care Inc.
Professional Co.
Promius Pharma

Dosage forms

Form	Route	Strength
Capsule	Oral	200 mg/1
Capsule	Oral	400 mg/1
Tablet	Oral
Tablet	Oral	100 mg
Tablet	Oral	200 mg
Tablet	Oral	400 mg

Prices

Unit description	Cost	Unit
Acebutolol hcl powder	7.08USD	g
Sectral 400 mg capsule	4.48USD	capsule
Sectral 200 mg capsule	3.37USD	capsule
Acebutolol HCl 400 mg capsule	1.39USD	capsule
Acebutolol 400 mg capsule	1.34USD	capsule
Sectral 400 mg Tablet	1.11USD	tablet
Acebutolol HCl 200 mg capsule	1.05USD	capsule
Acebutolol 200 mg capsule	1.01USD	capsule
Sectral 200 mg Tablet	0.56USD	tablet
Acebutolol 400 mg Tablet	0.51USD	tablet
Apo-Acebutolol 400 mg Tablet	0.51USD	tablet
Mylan-Acebutolol (Type S) 400 mg Tablet	0.51USD	tablet
Mylan-Acebutolol 400 mg Tablet	0.51USD	tablet
Novo-Acebutolol 400 mg Tablet	0.51USD	tablet
Nu-Acebutolol 400 mg Tablet	0.51USD	tablet
Rhotral 400 mg Tablet	0.51USD	tablet
Sectral 100 mg Tablet	0.37USD	tablet
Acebutolol 200 mg Tablet	0.26USD	tablet
Apo-Acebutolol 200 mg Tablet	0.26USD	tablet
Mylan-Acebutolol (Type S) 200 mg Tablet	0.26USD	tablet
Mylan-Acebutolol 200 mg Tablet	0.26USD	tablet
Novo-Acebutolol 200 mg Tablet	0.26USD	tablet
Nu-Acebutolol 200 mg Tablet	0.26USD	tablet
Rhotral 200 mg Tablet	0.26USD	tablet
Acebutolol 100 mg Tablet	0.17USD	tablet
Apo-Acebutolol 100 mg Tablet	0.17USD	tablet
Mylan-Acebutolol (Type S) 100 mg Tablet	0.17USD	tablet
Mylan-Acebutolol 100 mg Tablet	0.17USD	tablet
Novo-Acebutolol 100 mg Tablet	0.17USD	tablet
Nu-Acebutolol 100 mg Tablet	0.17USD	tablet
Rhotral 100 mg Tablet	0.17USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	136-138	Merck Index 13
water solubility	259 mg/L	Not Available
logP	1.71	HANSCH,C ET AL. (1995)
Caco2 permeability	-5.83	ADME Research, USCD

Predicted Properties

Property	Value	Source
Water Solubility	0.172 mg/mL	ALOGPS
logP	1.43	ALOGPS
logP	1.53	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	87.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	94.87 m³·mol^-1	ChemAxon
Polarizability	38.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9156
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.8957
P-glycoprotein substrate	Substrate	0.7378
P-glycoprotein inhibitor I	Non-inhibitor	0.8557
P-glycoprotein inhibitor II	Non-inhibitor	0.8664
Renal organic cation transporter	Non-inhibitor	0.9466
CYP450 2C9 substrate	Non-substrate	0.8102
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.5752
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.8721
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9639
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.849
Biodegradation	Not ready biodegradable	0.8538
Rat acute toxicity	2.0487 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9821
hERG inhibition (predictor II)	Non-inhibitor	0.8555

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom: Organic compounds
Super Class: Organic oxygen compounds
Class: Organooxygen compounds
Sub Class: Carbonyl compounds
Direct Parent: Alkyl-phenylketones
Alternative Parents: Acetophenones / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Aryl alkyl ketones / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds / Dialkylamines
show 4 more
Substituents: Alkyl-phenylketone / Acetophenone / Benzoyl / Phenol ether / Aryl alkyl ketone / Phenoxy compound / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / 1,2-aminoalcohol
show 16 more
Molecular Framework: Aromatic homomonocyclic compounds
External Descriptors: monocarboxylic acid amide, secondary amino compound, ether, aromatic amide, ethanolamines, propanolamine (CHEBI:2379)

Targets

Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	347	7.4	37	15655528

Details1. Beta-1 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Partial agonist

General Function: Receptor signaling protein activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name: ADRB1
Uniprot ID: P08588
Uniprot Name: Beta-1 adrenergic receptor
Molecular Weight: 51322.1 Da

References

van den Meiracker AH, Man in 't Veld AJ, Fischberg DJ, Molinoff PB, van Eck HJ, Boomsma F, Derkx FH, Schalekamp MA: Acute and long-term effects of acebutolol on systemic and renal hemodynamics, body fluid volumes, catecholamines, active renin, aldosterone, and lymphocyte beta-adrenoceptor density. J Cardiovasc Pharmacol. 1988 Apr;11(4):413-23. [PubMed:2453744]
Abrahamsson T: Characterization of the beta 1-adrenoceptor stimulatory effects of the partial beta 1-agonists acebutolol, xamoterol, H142/08 and H201/70. Eur J Pharmacol. 1989 May 2;164(1):121-8. [PubMed:2568935]
Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [PubMed:16268148]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details2. Beta-2 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Partial agonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name: ADRB2
Uniprot ID: P07550
Uniprot Name: Beta-2 adrenergic receptor
Molecular Weight: 46458.32 Da

References

Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [PubMed:16268148]
Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496]
Lima JJ: Relationship between beta adrenoceptor occupancy and receptor down-regulation induced by beta antagonists with intrinsic sympathomimetic activity. J Recept Signal Transduct Res. 1996 Sep-Nov;16(5-6):357-72. [PubMed:8968966]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [PubMed:27836712]
Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [PubMed:17125412]

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019]
Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [PubMed:8953513]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2019 10:34

Acebutolol

Identification

Structure for Acebutolol (DB01193)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

Enzymes

References

Transporters

References