1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol

• ChemBase ID: 270
• Molecular Formular: C19H29NO
• Molecular Mass: 287.43966
• Monoisotopic Mass: 287.22491455
• SMILES: OC(C1CCCCC1)(CCN1CCCC1)c1ccccc1
• Canonical SMILES: OC(c1ccccc1)(C1CCCCC1)CCN1CCCC1
• InChI: InChI=1S/C19H29NO/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
• InChIKey: WYDUSKDSKCASEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol
• IUPAC Traditional name: procyclidine
• Brand Name: Arpicolin; Elorine; Kemadrin; Kemadrine; Lergine; Metanin; Osnervan; Procyclid; Procyklidin; Prosyklidin; Spamol; Triciclidina; Triciloid; Tricoloid; Tricyclamol; Vagosin
• Synonyms: Prociclidina [INN-Spanish]; Procyclidinum [INN-Latin]; Procyclidine

Database IDs

• CAS Number: 77-37-2
• PubChem SID: 46505553; 160963733
• PubChem CID: 4919

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.840035
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.41974708
• LogD (pH = 7.4): 1.7523681
• Log P: 3.788117
• Molar Refractivity: 88.6042 cm^3
• Polarizability: 34.990223 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.13
• LOG S: -4.47
• Solubility (Water): 9.84e-03 g/l

PROPERTIES

Physical Property

• Solubility: Moderately soluble in water, ~ 30 mg/ml
• Hydrophobicity(logP): 4.2

DETAILS

DrugBank - DB00387

• Drug Groups: approved
• Description: A muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism. [PubChem]
• Indication: For the treatment of all forms of Parkinson's Disease, as well as control of extrapyramidal reactions induced by antipsychotic agents.
• Pharmacology: Procyclidine has an atropine-like action on parasympathetic-innervated peripheral structures including smooth muscle. It's antispasmodic effects are thought to be related to the blockage of central cholinergic receptors M1, M2 and M4. It is used to treat symptomatic Parkinsonism and extrapyramidal dysfunction caused by antipsychotic agents.
• Toxicity: LD₅₀=60 mg/kg (IV in mice)
• Affected Organisms: Humans and other mammals
• Protein Binding: Approximately 100% bound to albumin.
• References: Theodoridis GC, Stark L: Central role of solar information flow in pregenetic evolution. J Theor Biol. 1971 Jun;31(3):377-88. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Theodoridis GC, Stark L: Central role of solar information flow in pregenetic evolution. J Theor Biol. 1971 Jun;31(3):377-88. Pubmed