Homatropine

Homatropine (Equipin, Isopto Homatropine) is an anticholinergic medication that is an antagonist at muscarinic acetylcholine receptors and thus the parasympathetic nervous system. It is used in eye drops as a cycloplegic (to temporarily paralyze accommodation), and as a mydriatic (to dilate the pupil).

Homatropine
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa601006
ATC code
Legal status
Legal status
  • Rx only, not FDA approved, only sold in UK
Identifiers
IUPAC name
  • (N-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 2-hydroxy-2-phenylacetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.561
Chemical and physical data
FormulaC16H21NO3
Molar mass275.348 g·mol−1
3D model (JSmol)
SMILES
  • CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)C(O)c2ccccc2
InChI
  • InChI=1S/C16H21NO3/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11/h2-6,12-15,18H,7-10H2,1H3/t12-,13+,14+,15? Y
  • Key:ZTVIKZXZYLEVOL-MCOXGKPRSA-N Y
 NY (what is this?)  (verify)

The related chemical compound homatropine methylbromide (methylhomatropine) is a different medication. Homatropine is less potent than atropine and has a shorter duration of action. It is available as the hydrobromide salt. Homatropine is also given as an atropine substitute given to reverse the muscarinic and CNS effects associated with indirect cholinomimetic (anti-AChase) administration.

It is on the World Health Organization's List of Essential Medicines.[1]

Side effects

Contraindications

References
  1. World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
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