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 Date6.3089279E11 |
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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 Date6.3089279E11 |
Cmax
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 |
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 |
---|---|---|
[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 |
|
Effect of diuretic, beta-adrenoceptor blocking agent and their combination on elevated blood pressure and serum potassium: a cross-over study. | 1978 Oct |
|
[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: II. Loss of intraocular pressure control. | 1992 |
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Metipranolol-induced adverse reactions: I. The rechallenge study. | 1992 |
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Pharmacological intervention with platelet phospholipase A2. | 2001 |
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Contact dermatitis to topical drugs for glaucoma. | 2001 Dec |
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Cost analysis of glaucoma medications: a 3-year review. | 2002 Aug |
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Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies. | 2003 Aug |
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Inhibition of neutrophil migration and oxygen free radical release by metipranolol and timolol. | 2003 Aug |
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Zinc and energy requirements in induction of oxidative stress to retinal pigmented epithelial cells. | 2003 Oct |
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Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs. | 2003 Oct |
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[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
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Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms. | 2003 Sep 26 |
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Two-year follow-up of latanoprost 0.005% monotherapy after changing from previous glaucoma therapies. | 2004 Dec |
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Metipranolol blunts nitric oxide-induced lipid peroxidation and death of retinal photoreceptors: a comparison with other anti-glaucoma drugs. | 2004 Oct |
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[Contemporary possibilities and perspectives in the treatment of glaucoma]. | 2005 |
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The management of glaucoma and intraocular hypertension: current approaches and recent advances. | 2006 Jun |
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Flupirtine attenuates sodium nitroprusside-induced damage to retinal photoreceptors, in situ. | 2007 Jul 12 |
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Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells. | 2007 Jun 11 |
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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 |
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Recent advances in pharmacotherapy of glaucoma. | 2008 Oct |
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Parasympathetic regulation of heart rate in rats after 5/6 nephrectomy is impaired despite functionally intact cardiac vagal innervation. | 2009 Aug |
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Comparison of the analysis of beta-blockers by different techniques. | 2009 Dec 1 |
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Prenatal diagnosis and management of fetal Long QT syndrome. | 2009 Feb |
|
Safety and tolerability of zoledronic acid and other bisphosphonates in osteoporosis management. | 2010 |
|
Cardiovascular parameters in rat model of chronic renal failure induced by subtotal nephrectomy. | 2010 |
|
Topical administration of adrenergic receptor pharmaceutics and nerve growth factor. | 2010 Jul 21 |
|
Carteolol hydrochloride suppresses the generation of reactive oxygen species and rescues cell death after ultraviolet irradiation of cultured lens epithelial cells. | 2010 Oct 12 |
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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100000085958
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36592-77-5
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C77946
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314731
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SUB03267MIG
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34845
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ACTIVE MOIETY
SUBSTANCE RECORD