Details of the Drug

General Information of Drug (ID: DM4ES8F)

Drug Name

Penbutolol

Synonyms

Betapressin; Levatol; Levatolol; Levopenbutol; Lobeta; Paginol; Penbutololum; PENBUTOLOL SULFATE; HOE 893; HOE 893d; Betapressin (TN); Hostabloc (TN); L-Penbutolol; Levatol (TN); Levatolol (TN); Lobeta (TN); Paginol (TN); Penbutolol (INN); Penbutolol [INN:BAN]; Penbutololum [INN-Latin]; Penbutolol Sulfate (2:1); S(-)-Penbutolol; (-)-Penbutolol; (2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol; 1-(tert-Butylamino)-3-(o-cyclopentylphenoxy)propan-2-ol

Indication

Disease Entry	ICD 11	Status	REF
Hypertension	BA00-BA04	Approved	[1]
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Therapeutic Class

Antihypertensive Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

291.4

Logarithm of the Partition Coefficient (xlogp)

4.2

Rotatable Bond Count (rotbonds)

7

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

3

ADMET Property

Absorption: The absorption of drug is more than 92% []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Bioavailability: 93% of drug becomes completely available to its intended biological destination(s) [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 20 hours (in healthy persons), 25 hours (in healthy elderly persons), and 100 hours (in patients on renal dialysis) [4]
Metabolism: The drug is metabolized via the liver []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.9214 micromolar/kg/day [5]

Chemical Identifiers

Formula: C18H29NO2
IUPAC Name: (2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
Canonical SMILES: CC(C)(C)NC[C@@H](COC1=CC=CC=C1C2CCCC2)O
InChI: InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
InChIKey: KQXKVJAGOJTNJS-HNNXBMFYSA-N

Cross-matching ID

PubChem CID: 37464
ChEBI ID: CHEBI:7954
CAS Number: 38363-40-5
DrugBank ID: DB01359
TTD ID: D0W8SB
INTEDE ID: DR1249
ACDINA ID: D00513

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Antagonist	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Antileukoproteinase (SLPI)	OTUNFUU8	SLPI_HUMAN	Gene/Protein Processing	[8]
Bone morphogenetic protein 6 (BMP6)	OT9WN536	BMP6_HUMAN	Gene/Protein Processing	[8]
Cystine/glutamate transporter (SLC7A11)	OTKJ6PXW	XCT_HUMAN	Gene/Protein Processing	[8]
Hepatocyte growth factor receptor (MET)	OT7K55MU	MET_HUMAN	Gene/Protein Processing	[8]
Interleukin-1 alpha (IL1A)	OTPSGILV	IL1A_HUMAN	Gene/Protein Processing	[8]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[8]
Interleukin-24 (IL24)	OT4VUWH1	IL24_HUMAN	Gene/Protein Processing	[8]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[8]
Phosphatidylcholine translocator ABCB4 (ABCB4)	OTE6PY83	MDR3_HUMAN	Gene/Protein Processing	[9]
Proepiregulin (EREG)	OTRM4NQY	EREG_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Penbutolol

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Levamlodipine	DM92S6N	Moderate	Increased risk of cardiac depression by the combination of Penbutolol and Levamlodipine.	Hypertension [BA00-BA04]	[10]
Clevidipine butyrate	DMW4M97	Moderate	Increased risk of cardiac depression by the combination of Penbutolol and Clevidipine butyrate.	Hypertension [BA00-BA04]	[10]
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Coadministration of a Drug Treating the Disease Different from Penbutolol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Cariprazine	DMJYDVK	Moderate	Additive hypotensive effects by the combination of Penbutolol and Cariprazine.	Bipolar disorder [6A60]	[11]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Penbutolol and Atracurium.	Corneal disease [9A76-9A78]	[12]
Pasireotide	DMHM7JS	Moderate	Increased risk of atrioventricular block by the combination of Penbutolol and Pasireotide.	Cushing syndrome [5A70]	[13]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Penbutolol and OPC-34712.	Depression [6A70-6A7Z]	[11]
Mepenzolate	DM8YU2F	Moderate	Antagonize the effect of Penbutolol when combined with Mepenzolate.	Digestive system disease [DE2Z]	[14]
Belladonna	DM2RBWK	Moderate	Antagonize the effect of Penbutolol when combined with Belladonna.	Infectious gastroenteritis/colitis [1A40]	[15]
ITI-007	DMUQ1DO	Moderate	Additive hypotensive effects by the combination of Penbutolol and ITI-007.	Insomnia [7A00-7A0Z]	[11]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Penbutolol due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[13]
Siponimod	DM2R86O	Major	Increased risk of bradycardia by the combination of Penbutolol and Siponimod.	Multiple sclerosis [8A40]	[16]
Fingolimod	DM5JVAN	Major	Increased risk of bradycardia by the combination of Penbutolol and Fingolimod.	Multiple sclerosis [8A40]	[17]
Ozanimod	DMT6AM2	Moderate	Increased risk of bradycardia by the combination of Penbutolol and Ozanimod.	Multiple sclerosis [8A40]	[18]
Methylscopolamine	DM5VWOB	Moderate	Antagonize the effect of Penbutolol when combined with Methylscopolamine.	Peptic ulcer [DA61]	[15]
Silodosin	DMJSBT6	Moderate	Additive hypotensive effects by the combination of Penbutolol and Silodosin.	Prostate hyperplasia [GA90]	[19]
Iloperidone	DM6AUFY	Moderate	Additive hypotensive effects by the combination of Penbutolol and Iloperidone.	Schizophrenia [6A20]	[11]
Molindone	DMAH70G	Moderate	Additive hypotensive effects by the combination of Penbutolol and Molindone.	Schizophrenia [6A20]	[11]
Thiothixene	DMDINC4	Moderate	Additive hypotensive effects by the combination of Penbutolol and Thiothixene.	Schizophrenia [6A20]	[11]
Amisulpride	DMSJVAM	Moderate	Additive hypotensive effects by the combination of Penbutolol and Amisulpride.	Schizophrenia [6A20]	[11]
Asenapine	DMSQZE2	Moderate	Additive hypotensive effects by the combination of Penbutolol and Asenapine.	Schizophrenia [6A20]	[11]
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⏷ Show the Full List of 18 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Quinoline yellow WS	E00309	24671	Colorant
Simethicone	E00575	6433516	Antifoaming agent; Diluent; Water-repelling agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Ferric oxide black	E00522	16211978	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Hypromellose	E00634	Not Available	Coating agent
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Pregelatinized starch	E00674	Not Available	Binding agent; Diluent; Disintegrant
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⏷ Show the Full List of 12 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Penbutolol 20 mg tablet	20 mg	Oral Tablet	Oral
Penbutolol Sulfate 10mg tablet	10mg	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7263).
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	beta-Adrenergic receptor blockers--a group of chiral drugs: different effects of each enantiomer. Ceska Slov Farm. 2002 May;51(3):121-8.
7	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.
8	An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
9	Evaluating the Role of Multidrug Resistance Protein 3 (MDR3) Inhibition in Predicting Drug-Induced Liver Injury Using 125 Pharmaceuticals. Chem Res Toxicol. 2017 May 15;30(5):1219-1229. doi: 10.1021/acs.chemrestox.7b00048. Epub 2017 May 4.
10	Anastassiades CJ "Nifedipine and beta-blocker drugs." Br Med J 281 (1980): 1251-2. [PMID: 6107167]
11	Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
12	Chapple DJ, Clark JS, Hughes R "Interaction between atracurium and drugs used in anaesthesia." Br J Anaesth 55 Suppl 1 (1983): s17-22. [PMID: 6688011]
13	Canadian Pharmacists Association.
14	Briant RH, Dorrington RE, Ferry DG, Paxton JW "Bioavailability of metoprolol in young adults and the elderly, with additional studies on the effects of metoclopramide and probanthine." Eur J Clin Pharmacol 25 (1983): 353-6. [PMID: 6628522]
15	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
16	Cerner Multum, Inc. "Australian Product Information.".
17	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
18	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
19	Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]