U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of METIPRANOLOL

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

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OPTIPRANOLOL
Primary
OPTIPRANOLOL

Cmax

ValueDoseCo-administeredAnalytePopulation
33.8 ng/mL
40 mg single, oral
DESACETYLMETIPRANOLOL plasma
Homo sapiens
77.15 μg/L
40 mg single, oral
DESACETYLMETIPRANOLOL serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
111.4 ng × h/mL
40 mg single, oral
DESACETYLMETIPRANOLOL plasma
Homo sapiens
254.4 μg × h/L
40 mg single, oral
DESACETYLMETIPRANOLOL serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.271 h
40 mg single, oral
DESACETYLMETIPRANOLOL serum
Homo sapiens

PubMed

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.