| Chemical Properties | White Crystalline Solid |
| Originator | Kerlone,Carriere,France,1983 |
| Uses | Cardioselective β1-adrenergic blocker. An antihypertensive; antiglaucoma. |
| Uses | Cardioselective 1-adrenergic blocker. An antihypertensive; antiglaucoma |
| Definition | ChEBI: A propanolamine that is 3-aminopropane-1,2-diol in which the hydrogen of the primary hydoxy is substituted by a 4-[2-(cyclopropylmethoxy)ethyl]phenyl group and one of the hydrogens attached to the amino group is substituted by isopropyl. It is a selective
beta1-receptor blocker and is used in the treatment of glaucoma as well as hypertension, arrhythmias, and coronary heart disease. It is also used to reduce non-fatal cardiac events in patients with heart failure. |
| Manufacturing Process | (1) 1 g of sodium hydroxide pellets (0.025 mol) is added to a suspension of
3.8 g of 4-[2-(cyclopropylmethoxy)-ethyl]-phenol in 30 ml of water. When the
solution becomes homogenous, 2.3 ml of epichlorohydrin are added and the
mixture is stirred for 8 hours. It is then extracted with ether and the extract is
washed with water, dried over sodium sulfate and evaporated to dryness. The
compound is purified by passing it over a silica column. 2.4 g of 1-[4-[2-
(cyclopropylmethoxy)ethyl]-phenoxy]-2,3-epoxy-propane are thus obtained.
(2) 4.9 g of the preceding compound (0.02 mol) are condensed with 25 ml of
isopropylamine by contact for 8 hours at ambient temperature and then by
heating for 48 hours at the reflux temperature. After evaporation to dryness,
the compound obtained is crystallized from petroleum ether. 5 g (yield 80%)
of 2-[[4-(2-cyclopropylmethoxy)-ethyl]-phenoxy]-3-isopropylaminopropan-2-ol
are thus obtained, melting point 70° to 72°C.
The hydrochloride is prepared by dissolving the base in the minimum amount
of acetone and adding a solution of hydrochloric acid in ether until the pH is
acid. The hydrochloride which has precipitated is filtered off and is
recrystallized twice from acetone, melting point 116°C. |
| Brand name | Betoptic (Alcon); Kerlone (Sanofi Aventis). |
| Therapeutic Function | Beta-adrenergic blocker |
| Biological Activity | betaxolol is a cardioselective beta-adrenergic receptor blocking agent. betaxolol (5 mg/kg via i.p. injection) was administered at 24 and then 44 h following the final chronic cocaine administration. animals treated with betaxolol during cocaine withdrawal |
| Veterinary Drugs and Treatments | Betaxolol HCl is a specific Beta1 adrenergic blocking agent which
reduces aqueous humor production by decreasing cyclic-AMP
synthesis in the ciliary body. This drug is a suitable substitute for
timolol and because of its specific Beta1 activity, might be a first
choice Beta blocking agent for patients with concurrent respiratory
disease. Either levobunolol HCl or betaxolol HCl would be the first
choice Beta blocking agent in a feline patient with glaucoma and
asthma, although a topical carbonic anhydrates inhibitor should be
considered before a Beta blocking agent in this situation. Betaxolol
and the other Beta blockers should be used with caution in patients
with cardiac disease. |
| Metabolism | Absorption of an oral dose of betaxolol (Kerlone,
Betoptic) is almost complete. The drug is subject to a
slight first-pass effect such that the absolute bioavailability
of the drug is about 90%.Approximately 50% of
administered betaxolol binds to plasma proteins, and its
plasma half-life is about 20 hours; it is suitable for dosing
once per day.The primary route of elimination is by
liver metabolism, with only 15% of unchanged drug being
excreted. |
