ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate

• ChemBase ID: 952
• Molecular Formular: C30H32N2O2
• Molecular Mass: 452.58728
• Monoisotopic Mass: 452.24637827
• SMILES: O(C(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1)CC
• Canonical SMILES: CCOC(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1
• InChI: InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
• InChIKey: HYPPXZBJBPSRLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
• IUPAC Traditional name: diphenoxylate
• Brand Name: Lomotil
• Synonyms: Dea No. 9170; Difenossilato [Dcit]; Difenoxilato [INN-Spanish]; Diphenoxalate; Diphenoxylate Hydrochloride; Diphenoxylatum [INN-Latin]; Diphenoxylate

Database IDs

• CAS Number: 915-30-0
• PubChem SID: 46507130; 160964415
• PubChem CID: 13505

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.005932
• LogD (pH = 7.4): 4.756608
• Log P: 5.884015
• Molar Refractivity: 146.7619 cm^3
• Polarizability: 53.054455 Å^3
• Polar Surface Area: 53.33 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.74
• LOG S: -5.49
• Solubility (Water): 1.46e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.8 mg/ml
• Hydrophobicity(logP): 6.3

DETAILS

DrugBank - DB01081

• Drug Groups: illicit; approved
• Description: A meperidine congener used as an antidiarrheal, usually in combination with atropine. At high doses, it acts like morphine. Its unesterified metabolite difenoxin has similar properties and is used similarly. It has little or no analgesic activity. This medication is classified as a Schedule V under the Controlled Substances Act by the Food and Drug Administration (FDA) and the DEA in the United States when used in preparations. When diphenoxylate is used alone, it is classified as a Schedule II.
• Indication: For as adjunctive therapy in the management of diarrhea
• Pharmacology: Diphenoxylate, an antidiarrheal, is effective as adjunctive therapy in the management of diarrhea. Diphenoxylate is rapidly and extensively metabolized in man by ester hydrolysis to diphenoxylic acid (difenoxine), which is biologically active and the major metabolite in the blood.
• Toxicity: Coma, dry skin and mucous membranes, enlarged pupils of the eyes, extremely high body temperature, flushing, involuntary eyeball movement, lower than normal muscle tone, pinpoint pupils, rapid heartbeat, restlessness, sluggishness, suppressed breathing
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 90%
• Half Life: 12-14 hours
• Protein Binding: 74-95%
• External Links: Wikipedia; RxList