A metabolite of propranolol
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5-hydroxy Propranolol

Item No. 19880

Technical Information
Formal Name
5-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol
CAS Number
81907-82-6
Molecular Formula
C16H21NO3
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 50 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
226, 297, 314, 328 nm
SMILES
OC(CNC(C)C)COC1=CC=CC2=C1C=CC=C2O
InChi Code
InChI=1S/C16H21NO3/c1-11(2)17-9-12(18)10-20-16-8-4-5-13-14(16)6-3-7-15(13)19/h3-8,11-12,17-19H,9-10H2,1-2H3
InChi Key
WMYPGILKDMWISO-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    5-hydroxy Propranolol is a metabolite of propranolol (Item No. 17291), a β-adrenergic receptor antagonist.1 Propranolol is primarily metabolized in the liver, with cytochrome P450 isoform 2D6 directing ring hydroxylation and the generation of 5-hydroxy propranolol and related metabolites.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mehvar, R., and Brocks, D.R. Stereospecific pharmacokinetics and pharmacodynamics of β-adrenergic blockers in humans. J. Pharm. Pharm. Sci. 4(2), 185-200 (2001).

    2. Ellis, S.W., Hayhurst, G.P., Lightfoot, T., et alEvidence that serine 304 is not a key ligand-binding residue in the active site of cytochrome P450 2D6. Biochem J. 345(Pt 3), 565-571 (2000).

    3. Masubuchi, Y., Hosokawa, S., Horie, T., et alCytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab. Dispos. 22(6), 909-915 (1994).

    4. Ring, J.A., Ghabrial, H., Ching, M.S., et alFetal hepatic propranolol metabolism. Studies in the isolated perfused fetal sheep liver. Drug Metab. Dispos. 23(2), 190-196 (1995).

    Product Citations

    Negoro, R., Tasaka, M., Deguchi, S., et alGeneration of HepG2 cells with high expression of multiple drug-metabolizing enzymes for drug discovery research using a PITCh system. Cells 11(10), 1677 (2022).