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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 of METIPRANOLOL HYDROCHLORIDE

SMILES

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

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
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
[Effect of prolonged administration of beta-blockers on the hemodynamics of patients who have sustained a myocardial infarct].
1985 Sep
Metipranolol-induced adverse reactions: I. The rechallenge study.
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
The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol.
2003 Apr
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2003 Oct-Dec
Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004.
2006
The beta-adrenergic receptor antagonist metipranolol blunts zinc-induced photoreceptor and RPE apoptosis.
2006 Jul
The management of glaucoma and intraocular hypertension: current approaches and recent advances.
2006 Jun
Clinical investigation of the effect of topical anesthesia on intraocular pressure.
2007 Sep
Neurodegenerative diseases of the retina and potential for protection and recovery.
2008 Jun
Recent advances in pharmacotherapy of glaucoma.
2008 Oct
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 HYDROCHLORIDE
MI   ORANGE BOOK   VANDF   WHO-DD  
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
BETAMANN
Brand 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
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Code System Code Type Description
WIKIPEDIA
Metipranolol hydrochloride
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SMS_ID
100000085958
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CAS
36592-77-5
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NCI_THESAURUS
C77946
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RXCUI
314731
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EVMPD
SUB03267MIG
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FDA UNII
FBW237ALKD
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ChEMBL
CHEMBL1291
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PUBCHEM
656682
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MERCK INDEX
m7486
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CHEBI
34845
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DRUG BANK
DBSALT000806
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EPA CompTox
DTXSID80957866
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