U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H27NO4
Molecular Weight 309.4006
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METIPRANOLOL

SMILES

CC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C1

InChI

InChIKey=BQIPXWYNLPYNHW-UHFFFAOYSA-N
InChI=1S/C17H27NO4/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-14(6)19)13(5)12(16)4/h7,10,15,18,20H,8-9H2,1-6H3

HIDE SMILES / InChI
Metipranolol is a beta-adrenergic antagonist effective for both beta-1 and beta-2 receptors. It is used as an antiarrhythmic, antihypertensive, and antiglaucoma agent. Metipranolol blocks beta1 and beta2 (non-selective) adrenergic receptors. It does not have significant intrinsic sympathomimetic activity, and has only weak local anesthetic (membrane-stabilizing) and myocardial depressant activity. Orally administered beta-adrenergic blocking agents reduce cardiac output in both healthy subjects and patients with heart disease. In patients with severe impairment of myocardial function, beta-adrenergic receptor antagonists may inhibit the sympathetic stimulatory effect necessary to maintain adequate cardiac output. Metipranolol when applied topically in the eye, has the action of reducing elevated as well as normal intraocular pressure (IOP), whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss. The higher the level of intraocular pressure, the greater the likelihood of glaucomatous visual field loss and optic nerve damage. The primary mechanism of the ocular hypotensive action of Metipranolol is most likely due to reduction in aqueous humor production. A slight increase in outflow may be an additional mechanism. Metipranolol reduces IOP with little or no effect on pupil size or accommodation. Metipranolol is known as the brand OptiPranolol. Brand-name OptiPranolol is manufactured by Bausch & Lomb Incorporated. However, the patents for OptiPranolol have expired, and this medication is currently available in generic form. Generic OptiPranolol eye drops are available in one strength -- metipranolol 0.3 percent solution. It is made by Falcon Pharmaceuticals.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OPTIPRANOLOL

Approved Use

Metipranolol ophthalmic solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open angle glaucoma.

Launch Date

1989
Primary
OPTIPRANOLOL

Approved Use

Metipranolol ophthalmic solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open angle glaucoma.

Launch Date

1989
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
33.8 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESACETYLMETIPRANOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
77.15 μg/L
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESACETYLMETIPRANOLOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
111.4 ng × h/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESACETYLMETIPRANOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
254.4 μg × h/L
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESACETYLMETIPRANOLOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.271 h
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESACETYLMETIPRANOLOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Metipranolol-induced adverse reactions: II. Loss of intraocular pressure control.
1992
Cardiovascular considerations in using topical, oral, and intravenous drugs for the treatment of glaucoma and ocular hypertension: focus on beta-adrenergic blockade.
2001 Nov-Dec
Cost analysis of glaucoma medications: a 3-year review.
2002 Aug
Cationic amphiphilic drugs and platelet phospholipase A(2) (cPLA(2)).
2002 Feb 15
[Treatment of central serous chorioretinopathy with beta blockers].
2002 Nov
The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol.
2003 Apr
Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies.
2003 Aug
Inhibition of neutrophil migration and oxygen free radical release by metipranolol and timolol.
2003 Aug
Zinc and energy requirements in induction of oxidative stress to retinal pigmented epithelial cells.
2003 Oct
Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs.
2003 Oct
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2003 Oct-Dec
Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms.
2003 Sep 26
Two-year follow-up of latanoprost 0.005% monotherapy after changing from previous glaucoma therapies.
2004 Dec
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells.
2007 Jun 11
Patents

Sample Use Guides

Usual Adult Dose for Glaucoma (Open Angle) One drop in the affected eye(s) twice a day Comments: -If intraocular pressure is not at a satisfactory level on this regimen, use of more frequent administration or a larger dose is not known to be of benefit. -Concomitant therapy to lower intraocular pressure can be initiated with pilocarpine, epinephrine, or acetazolamide.
Route of Administration: Topical
Metipranolol 10 (-4) mol/l asignificantly decreased the aggregation response of rat platelets stimulated with collagen after each preincubation time studied.
Name Type Language
METIPRANOLOL
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
METIPRANOLOL [MART.]
Common Name English
(±)-1-(4-HYDROXY-2,3,5-TRIMETHYLPHENOXY)-3-(ISOPROPYLAMINO)-2-PROPANOL 4-ACETATE
Common Name English
BM01.004
Code English
METIPRANOLOL [MI]
Common Name English
VUAB-6453
Code English
PHENOL, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-2,3,6-TRIMETHYL-, (±)-, 1-ACETATE
Common Name English
D,L-METIPRANOLOL
Common Name English
Metipranolol [WHO-DD]
Common Name English
metipranolol [INN]
Common Name English
VUAB6453
Code English
METIPRANOLOL [VANDF]
Common Name English
BM-01.004
Code English
METIPRANOLOL [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC S01ED04
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
WHO-VATC QS01ED54
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
WHO-ATC C07BA68
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
NDF-RT N0000000161
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
WHO-ATC S01ED54
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
WHO-VATC QS01ED04
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
NDF-RT N0000175556
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
WHO-VATC QC07BA68
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4046078
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
MESH
D014290
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-151-5
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
EVMPD
SUB08892MIG
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
MERCK INDEX
m7486
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY Merck Index
IUPHAR
7239
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
LACTMED
Metipranolol
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL1291
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
NCI_THESAURUS
C61844
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
DRUG CENTRAL
1779
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
USAN
CC-51
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
WIKIPEDIA
METIPRANOLOL
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
SMS_ID
100000092160
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
CAS
22664-55-7
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
DRUG BANK
DB01214
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
FDA UNII
X39AL81KEB
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
INN
4372
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
PUBCHEM
31477
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY
RXCUI
10824
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY RxNorm
CHEBI
6897
Created by admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
PRIMARY