Procyclidine

Procyclidine

Systematic (IUPAC) name
1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a605037
Legal status	?
Routes	oral, im, iv
Pharmacokinetic data
Protein binding	~100%-albumin
Half-life	~12 h
Identifiers
CAS number	77-37-2 77-37-2 (free base)
ATC code	N04AA04
PubChem	CID 207841
DrugBank	DB00387
ChemSpider	4750
UNII	C6QE1Q1TKR Y
ChEMBL	CHEMBL1761 Y
Chemical data
Formula	C19H30ClNO
Mol. mass	323.9 g/mol
Y (what is this?)  (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.

Chemistry

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

• DE patent 1084734, E. Jassmann, H. Pfanz, "Verfahren zur Herstellung von tertiaeren Aminoalkoholen", issued 1960-07-07, assigned to VEB Fahlberg-List 
• US patent 2826590, E. M. Boffort, "Synthesis of tricyclamol", issued 1958-03-11, assigned to Eli Lilly 
• D. W. Adamson, P. A. Barrett, S. Wilkinson (1951). "11. Aminoalkyl tertiary carbinols and derived products. Part IV. Spasmolytics. Phenyl- and cyclohexylphenyl-carbinols". Journal of the Chemical Society 1951 (0): 52–60. doi:10.1039/JR9510000052. 

References

• British National Formulary (45 ed.). March 2003.