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etybenzatropine

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etybenzatropine

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Etybenzatropine (INN), also known as ethybenztropine (USAN, BAN) and tropethydrylin, is a synthetic anticholinergic and antihistamine drug previously marketed under the trade names Panolid, Ponalid, and Ponalide for the treatment of Parkinson's disease and parkinsonism. Structurally related to benzatropine, etybenzatropine combines a tropane backbone with antihistaminic properties, acting primarily as a muscarinic acetylcholine receptor antagonist. It was used to alleviate motor symptoms such as tremor and rigidity but has been discontinued due to limited efficacy, significant side effects, an

Chemical data

Formula
C22H27NO
Molecular weight
321.5 g/mol
IUPAC name
(1R,5R)-3-benzhydryloxy-8-ethyl-8-azabicyclo[3.2.1]octane
SMILES
CCN1[C@@H]2CC[C@@H]1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4
InChIKey
PHTMLLGDZBZXMW-WOJBJXKFSA-N
XLogP
4.8
Polar surface area
12.5 Ų
H-bond donors
0
H-bond acceptors
2
Formal charge
0

via PubChem

Wikidata facts

Mass
321.209264484
Show 4 more facts
chemical formula
C₂₂H₂₇NO
canonical SMILES
CCN1C2CCC1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4
defined daily dose
9
isomeric SMILES
CCN1[C@@H]2CC[C@@H]1CC(OC(c1ccccc1)c1ccccc1)C2
Sources (3)

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Encyclopedic overview

7 sections
Contents
  • Pharmacological properties
  • Medical use
  • Side effects
  • History
  • See also
  • References
  • External links

Etybenzatropine (INN), also known as ethybenztropine (USAN, BAN) and tropethydrylin, is a synthetic anticholinergic and antihistamine drug previously marketed under the trade names Panolid, Ponalid, and Ponalide for the treatment of Parkinson's disease and parkinsonism. Structurally related to benzatropine, etybenzatropine combines a tropane backbone with antihistaminic properties, acting primarily as a muscarinic acetylcholine receptor antagonist. It was used to alleviate motor symptoms such as tremor and rigidity but has been discontinued due to limited efficacy, significant side effects, and the availability of more effective antiparkinsonian therapies. Etybenzatropine may exhibit weak dopamine reuptake inhibitor activity, though this is not well-established.

== Pharmacological properties == Etybenzatropine is a centrally acting anticholinergic that blocks muscarinic acetylcholine receptors, particularly M1 receptors, in the basal ganglia, reducing the cholinergic-dopaminergic imbalance in parkinsonism. Its tropane structure, featuring a diphenylmethoxy group, enhances anticholinergic potency while conferring antihistaminic effects similar to pyrilamine. The antihistaminic activity contributes to sedation, a common side effect. Claims of dopamine reuptake inhibition, potentially increasing striatal dopamine, lack robust evidence and are considered speculative. Etybenzatropine’s oral bioavailability is low due to hepatic first-pass metabolism, with metabolites excreted in urine and bile.

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

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