(1R,3R,5S)-8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium bromide

• ChemBase ID: 399
• Molecular Formular: C17H32BrNO2
• Molecular Mass: 362.34548
• Monoisotopic Mass: 361.16164127
• SMILES: [C@H]12[N+]([C@@H](CC2)C[C@H](C1)OC(=O)C(CCC)CCC)(C)C.[Br-]
• Canonical SMILES: CCCC(C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)[N+]2(C)C)CCC.[Br-]
• InChI: InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1/t14-,15+,16+
• InChIKey: QSFKGMJOKUZAJM-CNKDKAJDSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S)-8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium bromide
• IUPAC Traditional name: (1R,3R,5S)-8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium bromide
• Brand Name: Anisotropine methobromide; Endovalpin; Lytispasm; Methyloctatropine bromide; Octatropine; Valpin 50
• Synonyms: Anisotropine Methylbromide; Anisotropine methyl bromide; 甲溴辛托品; 溴甲辛托品

Database IDs

• CAS Number: 80-50-2
• EC Number: 201-285-6
• MDL Number: MFCD00083234
• PubChem SID: 24890953; 160963862
• PubChem CID: 657201

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.66585374
• LogD (pH = 7.4): -0.66585374
• Log P: -0.66585374
• Molar Refractivity: 93.2643 cm^3
• Polarizability: 32.810318 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.4
• LOG S: -6.57
• Solubility (Water): 9.67e-05 g/l

PROPERTIES

Physical Property

• Solubility: 1600 mg/L
• Hydrophobicity(logP): 0.60

Safety Information

• RTECS: YM3710000
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 20/21/22-50/53
• Safety Statements: 36-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H400
• GHS Precautionary statements: P273-P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

DETAILS

DrugBank - DB00517

• Drug Groups: approved
• Description: Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.
• Indication: For use in conjunction with antacids or histamine H₂-receptor antagonists in the treatment of peptic ulcer, to reduce further gastric acid secretion and delay gastric emptying.
• Pharmacology: Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, by enzymatic hydrolysis.
• Absorption: Gastrointestinal absorption is poor and irregular. Total absorption after an oral dose is about 10 to 25%.
• Half Life: Not Known
• Protein Binding: Not Known