Metipranolol

Pair of enantiomers

S01ED04 (WHO) C07BA68 (WHO)

Identifiers

IUPAC name

(RS)-4-{[-2-hydroxy-3-(isopropylamino)propyl]oxy}-2,3,6-trimethylphenyl acetate

CAS Number

22664-55-7

PubChem CID

31477

IUPHAR/BPS

7239

DrugBank

DB01214^Y

ChemSpider

29193^Y

UNII

X39AL81KEB

KEGG

D02374^Y

ChEMBL

ChEMBL1291^Y

CompTox Dashboard (EPA)

DTXSID4046078

ECHA InfoCard100.041.031

Chemical and physical dataFormulaC₁₇H₂₇NO₄Molar mass309.406 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

SMILES

O=C(Oc1c(c(c(OCC(O)CNC(C)C)cc1C)C)C)C

InChI

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^Y
Key:BQIPXWYNLPYNHW-UHFFFAOYSA-N^Y

(verify)

Metipranolol (OptiPranolol, Betanol, Disorat, Trimepranol) is a non-selective beta blocker used in eye drops to treat glaucoma. It is rapidly metabolized into desacetylmetipranolol.^[1]

References

^ Maffei Facino R, Bertuletti R, Carini M, Tofanetti O (1980). "In vitro metabolism of methypranolol by rat liver". Analytical Chemistry Symposia Series. 4 (6): 217–223.

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Parasympathomimetics

muscarinic	Aceclidine Pilocarpine
muscarinic/nicotinic	Acetylcholine Carbachol
acetylcholinesterase inhibitors	Demecarium Ecothiopate Stigmine (Fluostigmine Neostigmine Physostigmine) Paraoxon