Bornaprine
subcutaneous, transdermal | |
| ATC code | |
|---|---|
| Pharmacokinetic data | |
| Elimination half-life | 30 hours |
| Excretion | Urine, feces |
| Identifiers | |
| |
JSmol) | |
| Density | 1.056 g/cm3 |
| Boiling point | 434.3 °C (813.7 °F) |
| |
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| (verify) | |
Bornaprine (brand name Sormodrem) is a
disorders, including hyperhidrosis.[3]
History
Bornaprine was first synthesized in 1960 by the
psychological symptoms.[7]
Pharmacodynamics
Bornaprine is an
affinity of antagonist for receptor) of 7.27 ± 0.21 indicating a high potency.[12]
Pharmacokinetics
Absorption
Bornaprine is successfully
humans within 1–2 hours after an oral dose.[13] Additional oral doses of bornaprine resulted in some accumulation in the plasma.[13]
Excretion
Single oral doses of bornaprine were successfully
dogs, and humans.[13] The following mean excretion rates were also reported during five days for urine and feces: rat 31 and 70%, dog 53 and 39%, and humans 78 and 4%.[13] Excretion was notably prolonged and incomplete at five days in humans, indicating a longer half life and metabolism rate of bornaprine for humans.[13] In human subjects, bornaprine has a half life of approximately 30 hours compared to 5 and 12 hour half lives in rats and dogs, respectively.[13]
Metabolites
Bornaprine is an epimeric mixture of
isomers of monohydroxy-N-desthel-sormodren, three isomers of monohydroxy-sormodren and 5-hydroxyl.[13] Each of these metabolites were hydroxylated at either C-5 or C-6 in the bicyclic ring.[14] The activity of each of compounds has been studied extensively and 5-hydroxyl showed similar anticholinergic activity to the parent compound when tested in isolated rat atrium unlike other identified metabolites.[12]
Availability
Bornaprine is currently available under the brand name Sormodrem in the following countries: Austria (
Abbott Pharmaceuticals), Germany (Abbott), Italy (Teofarma Pharmaceuticals), and Turkey (Abbott). Bornaprine is normally administered in a tablet form, however a recent patent is investigating the effect of several anticholinergic drugs, including bornaprine, in transdermal patches
. These patches are not currently available to the public market. Bornaprine is not currently on the market in the United States and its clinical trial status is unknown.
Treatment
Parkinson's disease
Like many other anticholinergic drugs, bornaprine had been used to treat the symptoms of Parkinson's disease. Bornaprine most effectively treats the tremors associated with Parkinson's and also helps
posture and facial expression.[1]
Hyperhidrosis
prescribed for treating hyperhidrosis in Europe
.
Sleep
When administered to healthy humans, bornaprine suppressed the amount of
sleep aid in the future.[10]
Side effects
Since bornaprine is a potent anticholinergic drug, it has a similar side effect profile to other anticholinergic drugs, including
dry mouth and constipation.[15][1] Additionally, when bornaprine was administered to patients with secondary parkinsonism, few patients reported transient confusion.[11]
Toxicity
convulsions.[16]
Synthesis
Bornaprine can be synthesized beginning with
Catalytic hydrogenation over Raney nickel
gives 2-phenylbicyclo[2.2.1]heptane-2-carboxylic acid (5). Conversion of the acid to the acid chloride and esterification with 3-diethylaminopropanol (4) completes the synthesis of bornaprine (6).
Synthesis of bornaprine
References
- ^ PMID 3514543.
- ISBN 978-3-85200-181-4.
- ^ PMID 18332889.
- ^ a b Haas H (1960). "3-Piperidino-1-phenyl-1-(bicyclo[2.2.1]hept-5-en-2-yl)-1-propanol (Akineton). II". Archives Internationales de Pharmacodynamie (in German). 78: 204–38.
- ^ a b Haas H, Wulzinger H (1960). "3-Piperidino-1-phenyl-1-(bicyclo[2.2.1]hept-5-en-2-yl)-1-propanol (Akineton). III". Archives Internationales de Pharmacodynamie Therapy (in German). 78: 239–52.
- ^ a b Haas H (1964). "Supplementary investigations of the spasmolytic bicyclophenamine (β-pyrrolidinylethyl 2-phenylbicyclo[2.2.1]heptane-2-carboxylate)". Arzneimittel-Forschung (in German). 14: 342–7.
- ^ a b c Avenarius HJ, Gesterbrandt F (1968). "Kr 339, ein neus tremorhemmendes Praparat zu Behandlung des Parkinson Syndromes". Wien klin Wochenschr (in German) (80th ed.).
- ^ Kreiskott H, Kretzschmar R (1985). "Neuere pharmakologische Aspekte zu den zentralen Anticholinergika Biperiden und Bornaprin". Das Parkinson-Syndrom (in German). pp. 277–87.
- PMID 790774.
- ^ PMID 7945741.
- ^ PMID 6500902.
- ^ PMID 2057518.
- ^ PMID 7210700.
- PMID 3735109.
- PMID 4058785.
- ^ a b "Bornaprine". United States National Library of Medicine. National Institute of Health. Retrieved 1 March 2014.
- ^ DE1044809, Kraft Helmut, Klavehn Wilfrid, U.S. patent 3,083,204 (1963 to Knoll Ag).