metipranolol

Trade name: optipranolol

Small moleculeapproved

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

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Timeline

1980s

  1. Dec 29, 1989

    Bausch & Lomb — Earliest FDA Approval

  2. Dec 29, 1989

    Bausch & Lomb — NDA Organization

2000s

  1. Aug 6, 2001

    Sandoz — Marketing Organization

  2. Aug 6, 2001

    Novartis — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedDec 29, 1989

Chemistry & pharmacology

Loading structure…

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

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)

OrganizationOrg typeRelationshipDate
Bausch & LombFor profitNDADec 29, 1989
NovartisFor profitMKTGAug 6, 2001
SandozFor profitMKTGAug 6, 2001
SandozFor profitSYNAug 6, 2001