homatropine

Also known as 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester, (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2-phenylacetate

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).

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 461770217
Drug.image: Homatropine.svg
Drug.image_class: skin-invert-image
Drug.MedlinePlus: a601006
Drug.legal_status: Rx only
Drug.CAS_number: 87-00-3
Drug.ATC_prefix: S01
Drug.ATC_suffix: FA05
Drug.PubChem: 6321423
Drug.DrugBank: DB00725
Drug.ChemSpiderID: 16498795
Drug.UNII: 8QS6WCL55Z
Drug.ChEMBL: 1233442
Drug.IUPAC_name: (N-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 2-hydroxy-2-phenylacetate
Drug.C: 16
Drug.H: 21

via Wikipedia infobox

Chemical data

Formula: C16H21NO3
Molecular weight: 275.34 g/mol
IUPAC name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2-hydroxy-2-phenylacetate
SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(C3=CC=CC=C3)O
InChIKey: ZTVIKZXZYLEVOL-DGKWVBSXSA-N
XLogP: 1.9
Polar surface area: 49.8 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

321 papers

Homatropine.2006
Systemic toxicity from ocular homatropine.Academic emergency medicine : official journal of the Society for Academic Emergency Medicine · 1996
Treatment of Non-Infectious Corneal Injury: Review of Diagnostic Agents, Therapeutic Medications, and Future Targets.Drugs · 2022
The interaction between homatropine and optical blur on choroidal thickness.Ophthalmic & physiological optics : the journal of the British College of Ophthalmic Opticians (Optometrists) · 2018
Comparing homatropine and atropine in pediatric cycloplegic refractions.Journal of AAPOS : the official publication of the American Association for Pediatric Ophthalmology and Strabismus · 2011

via PubMed

Wikidata facts

Subclass of: medication
Mass: 275.152144

Show 5 more facts

canonical SMILES: CN1C2CCC1CC(C2)OC(=O)C(C3=CC=CC=C3)O
chemical formula: C₁₆H₂₁NO₃
isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(C3=CC=CC=C3)O
subject has role: parasympatholytic
Commons category: Homatropine

Sources (1)

wikidata.org

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Encyclopedic overview

3 sections

Contents

Side effects
Contraindications
References

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.

Excerpted from Wikipedia’s “homatropine” article, available under the CC BY-SA 4.0 licence.

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