4-{[4-(acetyloxy)phenyl](pyridin-2-yl)methyl}phenyl acetate

• ChemBase ID: 109149
• Molecular Formular: C22H19NO4
• Molecular Mass: 361.39056
• Monoisotopic Mass: 361.13140809
• SMILES: CC(=O)Oc1ccc(cc1)C(c1ccc(OC(=O)C)cc1)c1ccccn1
• Canonical SMILES: CC(=O)Oc1ccc(cc1)C(c1ccccn1)c1ccc(cc1)OC(=O)C
• InChI: InChI=1S/C22H19NO4/c1-15(24)26-19-10-6-17(7-11-19)22(21-5-3-4-14-23-21)18-8-12-20(13-9-18)27-16(2)25/h3-14,22H,1-2H3
• InChIKey: KHOITXIGCFIULA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[4-(acetyloxy)phenyl](pyridin-2-yl)methyl}phenyl acetate
• IUPAC Traditional name: bicol; 4-{[4-(acetyloxy)phenyl](pyridin-2-yl)methyl}phenyl acetate
• Synonyms: 4,4'-DIACETOXYDIPHENYLPYRIDYL-2-METHANE; Bisacodyl; 4,4'-(2-Pyridinylmethylene)bisphenol 1,1'-Diacetate; 4,4'-(2-Pyridylmethylene)diphenol Diacetate; Bicol; Bis(p-acetoxyphenyl)-2-pyridylmethane; Brocalax; Broxalax; Dulcolax; Perilax; Stadalax; Bisacodyl; Acetphenolpicoline; Eufrecton; (Pyridin-2-ylmethylene)bis(4,1-phenylene) diacetate; 比沙可啶

Database IDs

• CAS Number: 30652-11-0; 603-50-9
• EC Number: 210-044-4
• MDL Number: MFCD00038039
• PubChem SID: 162094983; 24891588
• PubChem CID: 2391
• ATC CODE: A06AB02; A06AG02
• CHEMBL: 942
• Chemspider ID: 2299
• KEGG ID: D00245
• Unique Ingredient Identifier: 10X0709Y6I
• Wikipedia Title: Bisacodyl
• Medline Plus: a601027

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.5969257
• LogD (pH = 7.4): 3.6123946
• Log P: 3.6125956
• Molar Refractivity: 100.1488 cm^3
• Polarizability: 39.222076 Å^3
• Polar Surface Area: 65.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 132-134°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: SM8750000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Admin Routes: Oral, rectal
• Bioavailability: 15%
• Excretion: primarily in the feces, systemically absorbed drug is excreted in the urine
• Half Life: 16 Hours
• Metabolism: Hepatic (CYP450-mediated)
• Legal Status: OTC
• Pregnancy Category: C
• Gene Information: human ... CHRM4(1132)
• Mechanism of Action: Alters electrolyte secretion; Alters water secretion; Stimulates myenteric-plexus

Product Information

• Purity: 95+%
• Grade: analytical standard, for drug analysis
• Salt Data: Free Base
• Application(s): Cathartic; Laxative
• Empirical Formula (Hill Notation): C22H19NO4

DETAILS

MP Biomedicals - 05210023

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - B400800

Cathartic.

REFERENCES

• Schmidt, et al.: Arzneim.-Forsch., 3, 19 (1953)
• Wald, A., et al.: J. Clin. Gastroenterol., 36, 386 (1953)
• Schmidt, L. et al., Arzneim.-Forsch., 1953, 3, 19; 1956, 6, 22, (pharmacol)
• Schultz, O.E. et al., Arch. Pharm. (Weinheim, Ger.), 1955, 288, 234, (synth, pharmacol)
• Rubinstein, K. et al., Acta Chem. Scand., 1958, 12, 1274, (synth)
• Bruzzese, T. et al., Farmaco, Ed. Sci., 1973, 28, 121, (props)
• Sund, R.B., Norv. Pharm. Acta, 1983, 45, 125, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6443
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1205-120