methylbis(propan-2-yl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium bromide

• ChemBase ID: 662
• Molecular Formular: C23H30BrNO3
• Molecular Mass: 448.3932
• Monoisotopic Mass: 447.14090583
• SMILES: O(CC[N+](C(C)C)(C(C)C)C)C(=O)C1c2c(Oc3c1cccc3)cccc2.[Br-]
• Canonical SMILES: O=C(C1c2ccccc2Oc2c1cccc2)OCC[N+](C(C)C)(C(C)C)C.[Br-]
• InChI: InChI=1S/C23H30NO3.BrH/c1-16(2)24(5,17(3)4)14-15-26-23(25)22-18-10-6-8-12-20(18)27-21-13-9-7-11-19(21)22;/h6-13,16-17,22H,14-15H2,1-5H3;1H/q+1;/p-1
• InChIKey: XLBIBBZXLMYSFF-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: methylbis(propan-2-yl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium bromide
• IUPAC Traditional name: propantheline bromide; diisopropyl(methyl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium bromide
• Brand Name: Pro-Banthine; Propanthel
• Synonyms: Propantheline Bromide; Propanthelinium; Propanthelinum; Propantheline; 2-Hydroxyethyl]diisopropylmethyl-ammonium bromide xanthene-9-carboxylate; PROPANTHELINE BROMIDE; (2-Hydroxyethyl)diisopropylmethylammonium bromide xanthene-9-carboxylate; Propantheline bromide; N-Methyl-N-(1-methylethyl)-N-[2-[(9H-xanthen-9-ylcarbonyl)oxy]ethyl]-2-propanaminium Bromide; Corrigast; Ercorax; Ercotina; Ketaman; Kivatin; Neo-Metantyl; Neopepulsan; Pantas; Pervagal; Pro-Banthine; Pro-Gastron; Prodixamon; Propantel; SC 3171; β-Diisopropylaminoethyl Xanthene-9-carboxylate Methobromide

Database IDs

• CAS Number: 298-50-0; 50-34-0
• EC Number: 200-030-6
• MDL Number: MFCD00050291
• PubChem SID: 46507187; 24278660; 160964125
• PubChem CID: 9279; 4934

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.098024
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.36379364
• LogD (pH = 7.4): 0.36379364
• Log P: 0.36379364
• Molar Refractivity: 119.2545 cm^3
• Polarizability: 42.411964 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.66
• LOG S: -6.75
• Solubility (Water): 7.22e-05 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: soluble50 mg/mL; Methanol
• Apperance: White Solid; white to off-white powder
• Melting Point: 159-161 °C; 165-167°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: BP8249200
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Gene Information: human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

Product Information

• Purity: ≥97% (TLC)
• Linear Formula: C23H30NO3Br

DETAILS

MP Biomedicals - 02156392

Crystalline

DrugBank - DB00782

• Drug Groups: approved
• Description: A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking. [PubChem]
• Indication: For the treatment of enuresis. It has also been used for hyperhidrosis, and cramps or spasms of the stomach, intestines or bladder.
• Pharmacology: Propantheline is an anticholinergic drug, a medication that reduces the effect of acetylcholine, a chemical released from nerves that stimulates muscles, by blocking the receptors for acetylcholine on smooth muscle (a type of muscle). It also has a direct relaxing effect on smooth muscle. Propantheline is used to treat or prevent spasm in the muscles of the gastrointestinal tract in the irritable bowel syndrome. In addition, Propantheline inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions.
• Affected Organisms: Humans and other mammals
• Elimination: Approximately 70% of the dose is excreted in the urine, mostly as metabolites.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - P8891

Biochem/physiol Actions
Inhibits action of acetylcholine at post-ganglionic synapses; muscarinic acetylcholine receptor antagonist; antispasmodic; reduces gastric acid secretion.

Toronto Research Chemicals - P760900

Propantheline is an antimuscarinic agent used in the treatment of hyperhidrosis (excessive sweating), enuresis (involuntary urination) as well as cramps or spasms of the stomach, intestine and bladder.

REFERENCES

• Levin, R. et al.: Neurol. Urodyn., 1, 221 (1982)
• Daniotti, S. et al.: Br. J. Pharmacol., 82, 305 (1982)
• Moller, J. et al .: Acta Med. Scand., 184, 201 (1982)