Homatropine

Medication

S01FA05 (WHO)

Legal statusLegal status

In general: ℞ (Prescription only)

Identifiers

IUPAC name

(N-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 2-hydroxy-2-phenylacetate

CAS Number

87-00-3^N

PubChem CID

6321423

DrugBank

DB00725^N

ChemSpider

16498795^Y

UNII

8QS6WCL55Z

ChEMBL

ChEMBL1233442^N

CompTox Dashboard (EPA)

DTXSID6044014

ECHA InfoCard100.001.561

Chemical and physical dataFormulaC₁₆H₂₁NO₃Molar mass275.348 g·mol⁻¹3D model (JSmol)

Interactive image

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)

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).

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,^[1] given to reverse the muscarinic and CNS effects associated with indirect cholinomimetic (anti-AChase) administration.

Homatropine hydrobromide is on the World Health Organization's List of Essential Medicines.^[2]

Side effects

Blurred vision
Sensitivity to light

Contraindications

References

^ Scharer LL, Burhenne HJ (April 1964). "Megacolon associated with administration of an anticholinergic drug in a patient with ulcerative colitis". The American Journal of Digestive Diseases. 9 (4): 268–274. doi:10.1007/bf02232133. PMID 14142388. S2CID 19169565.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.