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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H29NO2
Molecular Weight 291.429
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENBUTOLOL

SMILES

CC(C)(C)NC[C@@]([H])(COc1ccccc1C2CCCC2)O

InChI

InChIKey=KQXKVJAGOJTNJS-HNNXBMFYSA-N
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

HIDE SMILES / InChI
Penbutolol is a new beta-adrenergic blocking drug approved for the treatment of hypertension. It is a noncardioselective beta-blocker and has intrinsic sympathomimetic activity. Penbutolol is marketed under the trade names Levatol, Levatolol, Lobeta, Paginol, Hostabloc, Betapressin. Penbutolol acts on the β1 adrenergic receptors in both the heart and the kidney. When β1 receptors are activated by catecholamines, they stimulate a coupled G protein that leads to the conversion of adenosine triphosphate (ATP) to cyclic adenosine monophosphate (cAMP). The increase in cAMP leads to activation of protein kinase A (PKA), which alters the movement of calcium ions in heart muscle and increases the heart rate. Penbutolol blocks the catecholamine activation of β1 adrenergic receptors and decreases heart rate, which lowers blood pressure. Levatol (Penbutolol) is indicated in the treatment of mild to moderate arterial hypertension. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LEVATOL

Approved Use

Levatol® is indicated in the treatment of mild to moderate arterial hypertension. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.

Launch Date

5.6782081E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
285 μg/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENBUTOLOL blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.21 h
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENBUTOLOL blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENBUTOLOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 mg 1 times / day single, intravenous
Studied dose
Dose: 4 mg, 1 times / day
Route: intravenous
Route: single
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 33- 62 years
n = 10
Health Status: unhealthy
Condition: ANGINA PECTORIS
Age Group: 33- 62 years
Sex: M
Population Size: 10
Sources:
120 mg 1 times / day steady, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: steady
Dose: 120 mg, 1 times / day
Sources:
unhealthy, 55.7 years (range: 43-64 years)
n = 8
Health Status: unhealthy
Age Group: 55.7 years (range: 43-64 years)
Sex: M+F
Population Size: 8
Sources:
40 mg 1 times / day steady, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, adult
n = 628
Health Status: unhealthy
Age Group: adult
Population Size: 628
Sources:
Disc. AE: Asthenia, Nausea...
AEs leading to
discontinuation/dose reduction:
Asthenia (0.6%)
Nausea (0.8%)
Depression (0.6%)
Dizziness (0.6%)
Headache (0.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Asthenia 0.6%
Disc. AE
40 mg 1 times / day steady, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, adult
n = 628
Health Status: unhealthy
Age Group: adult
Population Size: 628
Sources:
Depression 0.6%
Disc. AE
40 mg 1 times / day steady, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, adult
n = 628
Health Status: unhealthy
Age Group: adult
Population Size: 628
Sources:
Dizziness 0.6%
Disc. AE
40 mg 1 times / day steady, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, adult
n = 628
Health Status: unhealthy
Age Group: adult
Population Size: 628
Sources:
Headache 0.6%
Disc. AE
40 mg 1 times / day steady, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, adult
n = 628
Health Status: unhealthy
Age Group: adult
Population Size: 628
Sources:
Nausea 0.8%
Disc. AE
40 mg 1 times / day steady, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, adult
n = 628
Health Status: unhealthy
Age Group: adult
Population Size: 628
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The effect of clonidine and penbutolol, respectively on catecholamines in blood and urine, plasma renin activity and urinary aldosterone in hypertensive patients.
1975 Feb
Effect of oral penbutolol on renal haemodynamics of hypertensive patients with renal insufficiency.
1985 Aug 28
[Validity of the use of penbutolol in essential arterial hypertension].
1990 Jun
Decrease in penbutolol central response as a cause of changes in its serum protein binding.
1990 Mar
Penbutolol and carteolol: two new beta-adrenergic blockers with partial agonism.
1990 May
Decrease in penbutolol protein binding as a consequence of treatment with some alkylating agents.
1994
Thermotropic liquid crystalline drugs.
2005 Jul
Clinical review: aggressive management and extracorporeal support for drug-induced cardiotoxicity.
2007
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Patents

Sample Use Guides

The usual starting and maintenance dose of Levatol (Penbutolol), used alone or in combination with other antihypertensive agents, such as thiazide-type diuretics, is 20 mg given once daily. Doses of 40 mg and 80 mg have been well-tolerated but have not been shown to give a greater antihypertensive effect. The full effect of a 20- or 40-mg dose is seen by the end of 2 weeks. A dose of 10 mg also lowers blood pressure, but the full effect is not seen for 4 to 6 weeks.
Route of Administration: Oral
In Vitro Use Guide
Penbutolol (20 uM) significantly inhibited both the increase in [Ca2+]i and the cell-shape change induced by 15 uM LPC in rat isolated cardiomyocytes..
Name Type Language
PENBUTOLOL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
2-PROPANOL, 1-(2-CYCLOPENTYLPHENOXY)-3-((1,1-DIMETHYLETHYL)AMINO)-, (2S)-
Systematic Name English
PENBUTOLOL [VANDF]
Common Name English
PENBUTOLOL [MI]
Common Name English
(-)-1-TERT-BUTYLAMINO-2-HYDROXY-3-(2'-CYCLOPENTYLPHENOXY)PROPANE
Common Name English
PENBUTOLOL [WHO-DD]
Common Name English
PENBUTOLOL [INN]
Common Name English
(2S)-1-(TERT-BUTYLAMINO)-3-(2-CYCLOPENTYLPHENOXY)PROPAN-2-OL
Systematic Name English
Classification Tree Code System Code
WHO-ATC C07AA23
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
WHO-VATC QC07AA23
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
NDF-RT N0000175556
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
WHO-ATC C07CA23
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
LIVERTOX 751
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
NDF-RT N0000000161
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
WHO-VATC QC07CA23
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
Code System Code Type Description
PUBCHEM
37464
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
FDA UNII
78W62V43DY
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL1290
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
EVMPD
SUB09660MIG
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
LACTMED
Penbutolol
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
WIKIPEDIA
PENBUTOLOL
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
DRUG CENTRAL
2078
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
CAS
38363-40-5
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
RXCUI
7973
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY RxNorm
INN
3017
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
EPA CompTox
38363-40-5
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
IUPHAR
7263
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
DRUG BANK
DB01359
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
MESH
D010394
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY
MERCK INDEX
M8461
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C66336
Created by admin on Sat Jun 26 09:27:50 UTC 2021 , Edited by admin on Sat Jun 26 09:27:50 UTC 2021
PRIMARY