metipranolol
Trade name: optipranolol
Approved
Dec 29, 1989
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. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 3 marketing orgs
Timeline
1980s
- Dec 29, 1989
Bausch & Lomb — Earliest FDA Approval
- Dec 29, 1989
Bausch & Lomb — NDA Organization
Indications
Mechanism of action
- Beta-1 adrenergic receptorANTAGONIST
ADRB1 antagonist
- Beta-2 adrenergic receptorANTAGONIST
ADRB2 antagonist
Approval history
- approvedDec 29, 1989
Chemistry & pharmacology
SMILES
CC(=O)Oc1c(C)cc(OCC(O)CNC(C)C)c(C)c1C- Mol. weight
- 309.41 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
Yes
Sources
- ChEMBLCHEMBL1291 ↗
- WikipediaMetipranolol ↗
- NCATSFBW237ALKD ↗
- ChEMBLCHEMBL1200947 ↗
Also known as
- acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester
- acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester
- bm-01004
- bm-01004
- dl-metipranolol
- glauline
- methypranol
- metipranolol
- metipranolol
- metipranolol
- metipranolol
- metipranolol
- metipranolol
- metipranolol
- metipranolol
- metipranolol
- (+-)-metipranolol
- (+-)-metipranolol
- metipranolol hcl
- metipranolol hcl
- metipranolol hcl
- metipranolol hydrochloride
- metipranolol hydrochloride
- metipranolol hydrochloride
- metipranolol hydrochloride
- metipranolol hydrochloride
- metipranolol hydrochloride
- metipranolol hydrochloride
- metipranololum
- metipranololum
- optipranolol
- optipranolol
- optipranolol
- trimepranol
- vuab-6453
- vuab-6453
- vuab6453 (spofa)
- vuab6453 (spofa)
Organizations
Marketing (4)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Bausch & Lomb | For profit | NDA | Dec 29, 1989 |
| Novartis | For profit | MKTG | Aug 6, 2001 |
| Sandoz | For profit | MKTG | Aug 6, 2001 |
| Sandoz | For profit | SYN | Aug 6, 2001 |