(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one

• ChemBase ID: 956
• Molecular Formular: C11H16N2O2
• Molecular Mass: 208.25694
• Monoisotopic Mass: 208.12117776
• SMILES: O1C[C@@H]([C@H](CC)C1=O)Cc1n(cnc1)C
• Canonical SMILES: CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C
• InChI: InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
• InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one
• IUPAC Traditional name: pilocarpine
• Brand Name: Akarpine; Almocarpine; Ami-Pilo; Amistura P; Epicar; Isopto Carpine; Isoptocarpine; Mi-Pilo; Mi-Pilo Ophth Sol; Minims Pilocarpine; Miocarpine; Mistura P; Ocu-Carpine; Ocusert P 20; Ocusert Pilo; Ocusert Pilo-20; Ocusert Pilo-40; P.V. Carpine Liquifilm; Pilagan; Pilocar; Pilocar SMP; Pilocarpal; Pilocarpol; Pilocel; Pilokarpol; Pilomiotin; Pilopine HS; Piloptic-1; Piloptic-1/2; Piloptic-2; Piloptic-3; Piloptic-4; Piloptic-6; Pilostat; Pilovisc; Salagen; Sno Pilo; Syncarpine
• Synonyms: Pilocarpine chloride; Pilocarpine HCl; Pilocarpine hydrochloride; Pilocarpine monohydrochloride; Pilocarpine muriate; Pilokarpin monohydrochloride; Pilokarpin; Pilocarpin; Spersacarpine hydrochloride; Spersacarpine; Adsorbocarpine; Beta-pilocarpine hydrochloride; Pilocarpine

Database IDs

• CAS Number: 54-71-7
• PubChem SID: 160964419; 46507475
• PubChem CID: 5910

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.44190395
• LogD (pH = 7.4): 0.9023369
• Log P: 0.94975144
• Molar Refractivity: 56.5342 cm^3
• Polarizability: 21.845087 Å^3
• Polar Surface Area: 44.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.15
• LOG S: -2.0
• Solubility (Water): 2.07e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1000 mg/ml
• Hydrophobicity(logP): 1.1

DETAILS

DrugBank - DB01085

• Drug Groups: approved
• Description: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma. [PubChem]
• Indication: For the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.
• Pharmacology: Pilocarpine is a choline ester miotic and a positively charged quaternary ammonium compound. Pilocarpine, in appropriate dosage, can increase secretion by the exocrine glands. The sweat, salivary, lacrimal, gastric, pancreatic, and intestinal glands and the mucous cells of the respiratory tract may be stimulated. When applied topically to the eye as a single dose it causes miosis, spasm of accommodation, and may cause a transitory rise in intraocular pressure followed by a more persistent fall. Dose-related smooth muscle stimulation of the intestinal tract may cause increased tone, increased motility, spasm, and tenesmus. Bronchial smooth muscle tone may increase. The tone and motility of urinary tract, gallbladder, and biliary duct smooth muscle may be enhanced. Pilocarpine may have paradoxical effects on the cardiovascular system. The expected effect of a muscarinic agonist is vasodepression, but administration of pilocarpine may produce hypertension after a brief episode of hypotension. Bradycardia and tachycardia have both been reported with use of pilocarpine.
• Affected Organisms: Humans and other mammals
• Biotransformation: Possibly occurs at the neuronal synapses and in the plasma
• Absorption: There was a decrease in the rate of absorption of pilocarpine from SALAGEN Tablets when taken with a high fat meal by 12 healthy male volunteers
• Half Life: 0.76 hours
• External Links: Wikipedia; RxList; Drugs.com