A β-AR antagonist
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Alternative(s)
24003Metipranolol (hydrochloride)
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Metipranolol

Item No. 34089

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethylphenol, 1-acetate
CAS Number
22664-55-7
Molecular Formula
C17H27NO4
Formula Weight
309.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:6): 0.14 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
SMILES
CC1=C(OC(C)=O)C(C)=C(C)C(OCC(O)CNC(C)C)=C1
InChi Code
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
InChi Key
BQIPXWYNLPYNHW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $103

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    10 mg

    $153

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    25 mg

    $354

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    50 mg

    $653

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    Product Description

    Metipranolol is a β-adrenergic receptor (β-AR) antagonist.1 It binds to primary rabbit iris and ciliary body homogenates (Ki = 34 nM) and inhibits relaxation induced by isoproterenol (Item No. 15592) in guinea pig atrium and by fenoterol (Item No. 21293) in rat uterus (pA2s = 8.3 and 8.4, respectively). In vitro, metipranolol (100 μM) inhibits anoxia-induced cell death in primary rat retinal cells and sodium nitroprusside-induced lipid peroxidation in rat primary retinal homogenates.2,3 In vivo, topical ocular application of metipranolol (0.3%) decreases α-chymotrypsin-induced increases in intraocular pressure (IOP) in rabbits.1 It also inhibits the blinking response to ocular tactile stimulation in rabbits when administered topically to the eye at a dose of 0.6%. Formulations containing metipranolol have been used in the treatment of elevated IOP in patients with ocular hypertension or glaucoma.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sugrue, M.F., Armstrong, J.M., Gautheron, P.D., et al. A study on the ocular and extraocular pharmacology of metipranolol. Graefes. Arch. Clin. Exp. Ophthalmol. 222(3), 123-127 (1985).

    2. Wood, J.P.M., Schmidt, K.-G., Melena, J., et al. The β-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: Comparison with betaxolol. Exp. Eye Res. 76(4), 505-516 (2003).

    3. Osborne, N.N., and Wood, J.P.M. Metipranolol blunts nitric oxide-induced lipid peroxidation and death of retinal photoreceptors: A comparison with other anti-glaucoma drugs. Invest. Ophthalmol. Vis. Sci. 45(10), 3787-3795 (2004).