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
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | OPTIPRANOLOL Approved UseMetipranolol ophthalmic solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open angle glaucoma. Launch Date1989 |
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Primary | OPTIPRANOLOL Approved UseMetipranolol ophthalmic solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open angle glaucoma. Launch Date1989 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
T1/2
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 |
PubMed
Title | Date | PubMed |
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[Effect of prolonged administration of beta-blockers on the hemodynamics of patients who have sustained a myocardial infarct]. | 1985 Sep |
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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 |
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The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol. | 2003 Apr |
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[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
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Allergic contact dermatitis due to beta-blockers in eye drops: a retrospective analysis of multicentre surveillance data 1993-2004. | 2006 |
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The beta-adrenergic receptor antagonist metipranolol blunts zinc-induced photoreceptor and RPE apoptosis. | 2006 Jul |
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The management of glaucoma and intraocular hypertension: current approaches and recent advances. | 2006 Jun |
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Clinical investigation of the effect of topical anesthesia on intraocular pressure. | 2007 Sep |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21043897
Metipranolol 10 (-4) mol/l asignificantly decreased the aggregation response of rat platelets stimulated with collagen after each preincubation time
studied.
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NCI_THESAURUS |
C29576
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Metipranolol hydrochloride
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34845
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ACTIVE MOIETY
SUBSTANCE RECORD