Procyclidine: Difference between revisions

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{{distinguish|Phencyclidine}}
{{Drugbox
| verifiedrevid = 267631655
| IUPAC_name = 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride
| image = Procyclidine Wiki Str.png


<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|monograph|procyclidine-hydrochloride}}
| MedlinePlus = a605037
| pregnancy_category = 
| legal_status = 
| routes_of_administration = oral, [[intramuscular|im]], [[intravenous|iv]]
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = ~100%-albumin
| metabolism = 
| elimination_half-life = ~12 h
| excretion = 
<!--Identifiers-->
| CASNo_Ref = {{cascite}}
| CAS_number = 77-37-2
| CAS_supplemental = <br/>77-37-2 (free base) <!-- CAS verified -->
| ATC_prefix = N04
| ATC_suffix = AA04
| PubChem = 207841
| DrugBank = DB00387
| ChemSpiderID = 4750
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = C6QE1Q1TKR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1761
<!--Chemical data-->
| C=19 | H=30 | Cl=1 | N=1 | O=1
| molecular_weight = 323.9 g/mol
}}
'''Procyclidine''' is an [[anticholinergic]] [[medication|drug]] principally used for the treatment of drug-induced [[parkinsonism]], [[akathisia]] and acute [[dystonia]]; [[Parkinson disease]]; and [[idiopathic]] or secondary [[dystonia]].
== 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 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.
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==
[[File:Procyclidine synthesis.png|none|center|500px|Procyclidine synthesis: {{Cite patent|DE|1084734}} {{US patent|2826590}}]]
Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in exactly the 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 2.png|none|center|400px|Procyclidine synthesis 2<ref>{{cite journal|last1=Adamson|first1=D. W.|last2=Barrett|first2=P. A.|last3=Wilkinson|first3=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.
==See also==
*[[Biperidin]]
*[[Cycrimine]]
== References ==
{{Reflist}}
==Further reading==
* {{cite book | title=[[British National Formulary]] | edition=45 |date=March 2003}}
{{Antiparkinson}}
{{Cholinergics}}
{{Hallucinogens}}
[[Category:Alcohols]]
[[Category:Chlorides]]
[[Category:Muscarinic antagonists]]
[[Category:Pyrrolidines]]
[[Category:Tardive dyskinesia]]

Latest revision as of 13:49, 7 April 2015

Not to be confused with Phencyclidine.
Procyclidine
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa605037
Routes of
administration		oral, im, iv
ATC code
Pharmacokinetic data
Protein binding~100%-albumin
Elimination half-life~12 h
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H30ClNO
Molar mass323.9 g/mol
  (verify)

Procyclidine is an anticholinergic drug principally used for the treatment of drug-induced parkinsonism, akathisia and acute dystonia; Parkinson disease; and idiopathic or secondary dystonia.

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 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.

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 synthesis: DE 1084734  U.S. Patent 2,826,590
Procyclidine synthesis: DE 1084734  U.S. Patent 2,826,590

Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in exactly the same manner as was seen for trihexyphenidyl, except this time the linear synthesis begins with the preparation of 3-(1-pyrrolidino)propiophenone.

Procyclidine synthesis 2[1]
Procyclidine synthesis 2[1]

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.

See also

References

  1. ↑ Adamson, D. W.; Barrett, P. A.; Wilkinson, S. (1951). "11. Aminoalkyl tertiary carbinols and derived products. Part IV. Spasmolytics. Phenyl- and cyclohexylphenyl-carbinols". Journal of the Chemical Society (Resumed): 52. doi:10.1039/jr9510000052.

Further reading

Template:Antiparkinson

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