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
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
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 |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 |
|||
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 |
---|---|---|---|---|
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 |
---|---|---|
Metipranolol-induced adverse reactions: II. Loss of intraocular pressure control. | 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 |
|
Cationic amphiphilic drugs and platelet phospholipase A(2) (cPLA(2)). | 2002 Feb 15 |
|
[Treatment of central serous chorioretinopathy with beta blockers]. | 2002 Nov |
|
The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol. | 2003 Apr |
|
Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies. | 2003 Aug |
|
Inhibition of neutrophil migration and oxygen free radical release by metipranolol and timolol. | 2003 Aug |
|
Zinc and energy requirements in induction of oxidative stress to retinal pigmented epithelial cells. | 2003 Oct |
|
Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs. | 2003 Oct |
|
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
|
Beta-adrenergic receptor agonists and antagonists counteract LPS-induced neuronal death in retinal cultures by different mechanisms. | 2003 Sep 26 |
|
Two-year follow-up of latanoprost 0.005% monotherapy after changing from previous glaucoma therapies. | 2004 Dec |
|
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells. | 2007 Jun 11 |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
S01ED04
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
WHO-VATC |
QS01ED54
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
NCI_THESAURUS |
C29576
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
WHO-ATC |
C07BA68
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
NDF-RT |
N0000000161
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
WHO-ATC |
S01ED54
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
WHO-VATC |
QS01ED04
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
NDF-RT |
N0000175556
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
||
|
WHO-VATC |
QC07BA68
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID4046078
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
D014290
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
245-151-5
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
SUB08892MIG
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
m7486
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | Merck Index | ||
|
7239
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
Metipranolol
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
CHEMBL1291
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
C61844
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
1779
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
CC-51
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
METIPRANOLOL
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
100000092160
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
22664-55-7
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
DB01214
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
X39AL81KEB
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
4372
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
31477
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | |||
|
10824
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY | RxNorm | ||
|
6897
Created by
admin on Fri Dec 15 16:24:39 GMT 2023 , Edited by admin on Fri Dec 15 16:24:39 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)