METIPRANOLOL HYDROCHLORIDE

First approved in 1989

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H27NO4.ClH
Molecular Weight	345.862
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)NCC(O)COC1=CC(C)=C(OC(C)=O)C(C)=C1C

InChI

InChIKey=BLWNYSZZZWQCKO-UHFFFAOYSA-N

InChI=1S/C17H27NO4.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 163 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 2849
Beta-2 adrenergic receptor 209 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 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 52 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 8583	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 53 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 8583	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
Carteolol hydrochloride suppresses the generation of reactive oxygen species and rescues cell death after ultraviolet irradiation of cultured lens epithelial cells.	2010-10-12	21283534
Topical administration of adrenergic receptor pharmaceutics and nerve growth factor.	2010-07-21	20668722
Novel neuroprotective strategies in ischemic retinal lesions.	2010-02-03	20386654
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
Comparison of the analysis of beta-blockers by different techniques.	2009-12-01	19879818
Parasympathetic regulation of heart rate in rats after 5/6 nephrectomy is impaired despite functionally intact cardiac vagal innervation.	2009-08	19321759
Prenatal diagnosis and management of fetal Long QT syndrome.	2009-02	18709401
Recent advances in pharmacotherapy of glaucoma.	2008-10	20040958
Neurodegenerative diseases of the retina and potential for protection and recovery.	2008-06	19305795
Chronic atropine administration diminishes the contribution of vasoactive intestinal polypeptide to heart rate regulation.	2008	18052688
Clinical investigation of the effect of topical anesthesia on intraocular pressure.	2007-09	19668485
Flupirtine attenuates sodium nitroprusside-induced damage to retinal photoreceptors, in situ.	2007-07-12	17562394
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells.	2007-06-11	17615544
Ocular carteolol: a review of its use in the management of glaucoma and ocular hypertension.	2007	17571916
The beta-adrenergic receptor antagonist metipranolol blunts zinc-induced photoreceptor and RPE apoptosis.	2006-07	16799065
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006-06	18360593
Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004.	2006	17106597
Invited review: Neuroprotective properties of certain beta-adrenoceptor antagonists used for the treatment of glaucoma.	2005-06	15969634
[Drug induced uveitis].	2005-03	15803424
[Contemporary possibilities and perspectives in the treatment of glaucoma].	2005	16496599
Two-year follow-up of latanoprost 0.005% monotherapy after changing from previous glaucoma therapies.	2004-12	15684807
Metipranolol blunts nitric oxide-induced lipid peroxidation and death of retinal photoreceptors: a comparison with other anti-glaucoma drugs.	2004-10	15452090
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].	2004-02-20	14971294
Zinc and energy requirements in induction of oxidative stress to retinal pigmented epithelial cells.	2003-10	14570397
Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs.	2003-10	12898280
Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms.	2003-09-26	12967722
Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies.	2003-08	12900875
Inhibition of neutrophil migration and oxygen free radical release by metipranolol and timolol.	2003-08	12837974
The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol.	2003-04	12634114
[Treatment of central serous chorioretinopathy with beta blockers].	2002-11	12629852
Cost analysis of glaucoma medications: a 3-year review.	2002-08	12169974
Cardiovascular considerations in using topical, oral, and intravenous drugs for the treatment of glaucoma and ocular hypertension: focus on beta-adrenergic blockade.	2002-04-27	11975823
Cationic amphiphilic drugs and platelet phospholipase A(2) (cPLA(2)).	2002-02-15	12031829
Contact dermatitis to topical drugs for glaucoma.	2001-12	11753897
Pharmacological intervention with platelet phospholipase A2.	2001	11802290
Metipranolol-induced adverse reactions: II. Loss of intraocular pressure control.	1992	1359979
Metipranolol-induced adverse reactions: I. The rechallenge study.	1992	1359978
[Effect of prolonged administration of beta-blockers on the hemodynamics of patients who have sustained a myocardial infarct].	1985-09	2867243
Effect of diuretic, beta-adrenoceptor blocking agent and their combination on elevated blood pressure and serum potassium: a cross-over study.	1978-10	29653
[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)].	1977-02	841267

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 `Mon Mar 31 18:27:06 GMT 2025` Edited by `admin` on `Mon Mar 31 18:27:06 GMT 2025`
Record UNII	FBW237ALKD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BETAMANN

Preferred Name

English

METIPRANOLOL HYDROCHLORIDE

Common Name

English

1-(2,3,5-TRIMETHYL-4-ACETOXYPHENOXY)-3(ISOPROPYLAMINO)-2-PROPANOL MONOHYDRO CHLORIDE

Common Name

English

METIPRANOLOL HYDROCHLORIDE [MI]

Common Name

English

PHENOL, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-2,3,6-TRIMETHYL-, 1-ACETATE, HYDROCHLORIDE

Common Name

English

(±)-1-(4-HYDROXY-2,3,5-TRIMETHYLPHENOXY)-3-(ISOPROPYLAMINO)-2-PROPANOL 4-ACETATE HYDROCHLORIDE

Common Name

English

METIPRANOLOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

METIPRANOLOL HCL

Common Name

English

Metipranolol hydrochloride [WHO-DD]

Common Name

English

METIPRANOLOL HYDROCHLORIDE [VANDF]

Common Name

English

OPTIPRANOLOL

Brand Name

English

PHENOL, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-2,3,6-TRIMETHYL-, 1-ACETATE, HYDROCHLORIDE (1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576