METIPRANOLOL

US Previously Marketed

First approved in 1989

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 Search

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

Molecular Formula	C17H27NO4
Molecular Weight	309.4006
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=699ce415-0798-4244-b5ec-bcdb383b50b3&type=display | https://www.drugs.com/pro/metipranolol.html | http://glaucoma.emedtv.com/optipranolol/generic-optipranolol.html

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=699ce415-0798-4244-b5ec-bcdb383b50b3&type=display \| https://www.ncbi.nlm.nih.gov/pubmed/7907875 \| https://www.ncbi.nlm.nih.gov/pubmed/2858433	Antagonist 2778
Beta-2 adrenergic receptor 203 Target ID: CHEMBL3754 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=699ce415-0798-4244-b5ec-bcdb383b50b3&type=display \| https://www.ncbi.nlm.nih.gov/pubmed/7907875 \| https://www.ncbi.nlm.nih.gov/pubmed/2858433 \| https://www.ncbi.nlm.nih.gov/pubmed/2885244	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 50 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=699ce415-0798-4244-b5ec-bcdb383b50b3&type=display http://glaucoma.emedtv.com/optipranolol/generic-optipranolol.html	Primary		Approved 8429	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
Open-angle glaucoma 51 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=699ce415-0798-4244-b5ec-bcdb383b50b3&type=display http://glaucoma.emedtv.com/optipranolol/generic-optipranolol.html	Primary		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
33.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1971217	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6120080	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

Value	Dose	Co-administered	Analyte	Population
111.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1971217	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6120080	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.271 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6120080	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:34845	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34845
MolPort	MolPort-046-417-136	https://www.molport.com/shop/molecule-link/MolPort-046-417-136

PubMed

Title	Date	PubMed
[Reduction of aconitine and adrenaline tachycardia by the antifibrillating substance trimepranol in the rat heart in situ and in the isolated frog heart (comparative study) (author's transl)].	1977 Feb	841267
Effect of diuretic, beta-adrenoceptor blocking agent and their combination on elevated blood pressure and serum potassium: a cross-over study.	1978 Oct	29653
[Effect of prolonged administration of beta-blockers on the hemodynamics of patients who have sustained a myocardial infarct].	1985 Sep	2867243
Metipranolol-induced adverse reactions: II. Loss of intraocular pressure control.	1992	1359979
Metipranolol-induced adverse reactions: I. The rechallenge study.	1992	1359978
Pharmacological intervention with platelet phospholipase A2.	2001	11802290
Contact dermatitis to topical drugs for glaucoma.	2001 Dec	11753897
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	11975823
Cost analysis of glaucoma medications: a 3-year review.	2002 Aug	12169974
Cationic amphiphilic drugs and platelet phospholipase A(2) (cPLA(2)).	2002 Feb 15	12031829
[Treatment of central serous chorioretinopathy with beta blockers].	2002 Nov	12629852
The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol.	2003 Apr	12634114
Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies.	2003 Aug	12900875
Inhibition of neutrophil migration and oxygen free radical release by metipranolol and timolol.	2003 Aug	12837974
Zinc and energy requirements in induction of oxidative stress to retinal pigmented epithelial cells.	2003 Oct	14570397
Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs.	2003 Oct	12898280
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].	2003 Oct-Dec	14971294
Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms.	2003 Sep 26	12967722
Two-year follow-up of latanoprost 0.005% monotherapy after changing from previous glaucoma therapies.	2004 Dec	15684807
Metipranolol blunts nitric oxide-induced lipid peroxidation and death of retinal photoreceptors: a comparison with other anti-glaucoma drugs.	2004 Oct	15452090
[Contemporary possibilities and perspectives in the treatment of glaucoma].	2005	16496599
Invited review: Neuroprotective properties of certain beta-adrenoceptor antagonists used for the treatment of glaucoma.	2005 Jun	15969634
[Drug induced uveitis].	2005 Mar	15803424
Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004.	2006	17106597
The beta-adrenergic receptor antagonist metipranolol blunts zinc-induced photoreceptor and RPE apoptosis.	2006 Jul	16799065
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006 Jun	18360593
Ocular carteolol: a review of its use in the management of glaucoma and ocular hypertension.	2007	17571916
Flupirtine attenuates sodium nitroprusside-induced damage to retinal photoreceptors, in situ.	2007 Jul 12	17562394
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells.	2007 Jun 11	17615544
Clinical investigation of the effect of topical anesthesia on intraocular pressure.	2007 Sep	19668485
Chronic atropine administration diminishes the contribution of vasoactive intestinal polypeptide to heart rate regulation.	2008	18052688
Neurodegenerative diseases of the retina and potential for protection and recovery.	2008 Jun	19305795
Recent advances in pharmacotherapy of glaucoma.	2008 Oct	20040958
Parasympathetic regulation of heart rate in rats after 5/6 nephrectomy is impaired despite functionally intact cardiac vagal innervation.	2009 Aug	19321759
Comparison of the analysis of beta-blockers by different techniques.	2009 Dec 1	19879818
Prenatal diagnosis and management of fetal Long QT syndrome.	2009 Feb	18709401
Safety and tolerability of zoledronic acid and other bisphosphonates in osteoporosis management.	2010	21701624
Cardiovascular parameters in rat model of chronic renal failure induced by subtotal nephrectomy.	2010	20626224
Novel neuroprotective strategies in ischemic retinal lesions.	2010 Feb 3	20386654
Topical administration of adrenergic receptor pharmaceutics and nerve growth factor.	2010 Jul 21	20668722
Carteolol hydrochloride suppresses the generation of reactive oxygen species and rescues cell death after ultraviolet irradiation of cultured lens epithelial cells.	2010 Oct 12	21283534

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Metipranolol 10 (-4) mol/l asignificantly decreased the aggregation response of rat platelets stimulated with collagen after each preincubation time studied.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:24:39 GMT 2023` Edited by `admin` on `Fri Dec 15 16:24:39 GMT 2023`
Record UNII	X39AL81KEB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METIPRANOLOL

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