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{{Short description|Group of stereoisomers}}
{{Drugbox
| verifiedrevid = 267631655
| IUPAC_name = 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride
| image = Procyclidine-hydrochloride-2D-skeletal.png
<!--Clinical data-->
| tradename =
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| pregnancy_category =
| legal_status =
| routes_of_administration =
<!--Pharmacokinetic data-->
| bioavailability =
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| elimination_half-life = ~12 h
| excretion =
<!--Identifiers-->
| CAS_number = 77-37-2
| CAS_supplemental = <br/>77-37-2 (free base) <!-- CAS verified -->
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| ATC_suffix = AA04
| PubChem = 207841
| DrugBank =
| ChemSpiderID = 4750
| UNII_Ref = {{fdacite|correct|FDA}}
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1761
<!--Chemical data-->
| C=19 | H=30 | Cl=1 | N=1 | O=1
}}
'''Procyclidine''' is an [[anticholinergic]] [[medication|drug]] principally used for the treatment of
▲{{confuse|Phencyclidine}}
▲'''Procyclidine''' is an [[anticholinergic]] [[medication|drug]] principally used for the treatment of:
== Uses ==
It is used in patients with [[parkinsonism]] and [[akathisia]], and to reduce the side effects of [[antipsychotic]] treatment given for [[schizophrenia]]. Procyclidine is also a second-line drug for the treatment of [[Parkinson's disease]]. It improves [[tremor]] but not rigidity or [[bradykinesia]].▼
▲Procyclidine is also a second-line drug for the treatment of [[Parkinson's disease]]. It improves [[tremor]] but not rigidity or [[bradykinesia]].
Procyclidine is also sometimes used for the treatment of [[dystonia]] (but not [[tardive dyskinesia]]), a rare disorder that causes abnormal muscle contraction, resulting in twisting postures of limbs, trunk, or face.
== Overdose ==
Signs of procyclidine overdose are those of an [[anticholinergic]] and include confusion, agitation and sleeplessness that can last up to or more than 24 hours. Pupils become dilated and unreactive to light. [[Tachycardia]] (fast heart beat), as well as auditory and visual hallucinations have also been reported.
▲Signs of procyclidine overdose are those of an [[anticholinergic]] and include confusion, agitation and sleeplessness that can last up to or more than 24 hours. Pupils become dilated and unreactive to light. [[Tachycardia]] (fast heart beat), as well as auditory and visual hallucinations have also been reported.
Other known symptoms of overdose are: clumsiness or unsteadiness, being severely drowsy, having a severely dry mouth, nose, or throat, having an altered mood or other mental changes, seizures, being short of breath or having troubled breathing, a dry and warm, flushed skin.
A suspected overdose with severe life-threatening symptoms should immediately be brought to medical attention, where reversal can be attempted with [[physostigmine]] administered intravenously or subcutaneously.
==Synthesis==
Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in the exact same manner as was seen for [[trihexyphenidyl]], except this time the linear synthesis begins with the preparation of 3-(1-pyrrolidino)propiophenone.▼
[[File:Procyclidine synthesis.png|thumb|center|500px|Procyclidine synthesis:<ref>{{Cite patent|country=DE|number=1084734|pubdate=1960-07-07|title=Verfahren zur Herstellung von tertiäeren Aminoalkoholen [Process for the preparation of tertiary amino alcohols]|assign1=VEB Fahlberg-List Chemische und Pharmazeutische Fabriken|inventor1-last=Jassmann|inventor1-first=Edgar|inventor2-last=Pfanz|inventor2-first=Hermann}}</ref> {{US patent|2826590}}]]
▲Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in
[[File:Procyclidine synthesis2.png|thumb|center|400px|Procyclidine synthesis 2<ref>{{cite journal| vauthors = Adamson DW, Barrett PA, Wilkinson S |title=11. Aminoalkyl tertiary carbinols and derived products. Part IV. Spasmolytics. Phenyl- and cyclohexylphenyl-carbinols|journal=Journal of the Chemical Society (Resumed)|year=1951|pages=52|doi=10.1039/jr9510000052}}</ref>]]
In an interesting variation, the ketone is first reacted with phenylmagnesium bromide. [[Catalytic hydrogenation]] of the [[carbinol]] thus obtained can be stopped after the reduction of only one aromatic ring.
==Side Effects==
Side effects include nausea, constipation, urinary retention, blurred vision, anxiety, cognitive impairment, confusion, dizziness, gingivitis, hallucination, memory loss, rash and vomiting.
<ref>{{cite web |url=https://bnf.nice.org.uk/drug/procyclidine-hydrochloride.html |title=Procyclidine Hydrochloride |publisher=National Institute for Health and Care Excellence | access-date=2020-07-06}}</ref>
== See also ==
*[[Benzatropine]]
*[[Biperiden]]
*[[Cycrimine]]
== References ==
{{Reflist
* {{cite book | title=[[British National Formulary]] | edition=45 | year=2003 | month=March}}▼
== Further reading ==
▲* {{cite book | title=
{{Antiparkinson}}
{{
{{Muscarinic acetylcholine receptor modulators}}
[[Category:Chlorides]]▼
[[Category:Muscarinic antagonists]]
[[Category:1-Pyrrolidinyl compounds]]
[[Category:Tardive dyskinesia]]
[[Category:
▲[[Category:Pyrrolidines]]
▲[[Category:Chlorides]]
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