Oxyphenonium bromide
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MedKoo CAT#: 558258

CAS#: 50-10-2 (Br)

Description: Oxyphenonium bromide is a quaternary ammonium anticholinergic agent with peripheral side effects similar to those of atropine. It is used as an adjunct in the treatment of gastric and duodenal ulcer, and to relieve visceral spasms. The drug has also been used in the form of eye drops for mydriatic effect.


Chemical Structure

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Oxyphenonium bromide
CAS# 50-10-2 (Br)

Theoretical Analysis

MedKoo Cat#: 558258
Name: Oxyphenonium bromide
CAS#: 50-10-2 (Br)
Chemical Formula: C21H34BrNO3
Exact Mass:
Molecular Weight: 428.41
Elemental Analysis: C, 58.88; H, 8.00; Br, 18.65; N, 3.27; O, 11.20

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Related CAS #: 50-10-2 (Br); 14214-84-7 (free base)  

Synonym: 50-10-2; Spasmophen; Oxifenon; Oxyfenon; Oxyphenon; Atrenyl; Bromide Oxyphenonium; Chloride, Oxyphenonium; Iodide, Oxyphenonium; Metacin; Methacin; Oxyphenon

IUPAC/Chemical Name: 2-(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxyethyl-diethyl-methylazanium;bromide

InChi Key: 2-(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxyethyl-diethyl-methylazanium;bromide

InChi Code: InChI=1S/C21H34NO3.BrH/c1-4-22(3,5-2)16-17-25-20(23)21(24,18-12-8-6-9-13-18)19-14-10-7-11-15-19;/h6,8-9,12-13,19,24H,4-5,7,10-11,14-17H2,1-3H3;1H/q+1;/p-1

SMILES Code: CC[N+](C)(CC)CCOC(=O)C(C1CCCCC1)(C2=CC=CC=C2)O.[Br-]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 428.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: El-Gindy A, Emara S, Shaaban H. Stability-indicating method for determination of oxyphenonium bromide and its degradation product by high-performance liquid chromatography. J AOAC Int. 2007 Sep-Oct;90(5):1250-7. PubMed PMID: 17955969.

2: Funasaki N, Sumiyoshi T, Ishikawa S, Neya S. Solution structures of 1:1 complexes of oxyphenonium bromide with beta- and gamma-cyclodextrins. Mol Pharm. 2004 Mar-Apr;1(2):166-72. PubMed PMID: 15832513.

3: Funasaki N, Kawaguchi R, Hada S, Neya S. Ultraviolet spectroscopic estimation of microenvironments and bitter tastes of oxyphenonium bromide in cyclodextrin solutions. J Pharm Sci. 1999 Aug;88(8):759-62. PubMed PMID: 10430538.

4: Funasaki N, Kawaguchi R, Ishikawa S, Hada S, Neya S, Katsu T. Quantitative estimation of the bitter taste intensity of oxyphenonium bromide reduced by cyclodextrins from electromotive force measurements. Anal Chem. 1999 May 1;71(9):1733-6. doi: 10.1021/ac981286h. PubMed PMID: 21662814.

5: Joseph T, Venkataraman V, Nagarani A, David J, Bhatt A, Vaidya A. Safety pharmacology of a combination of tinidazole and oxyphenonium bromide. Arzneimittelforschung. 1997 Jul;47(7):869-72. PubMed PMID: 9272247.

6: Dharmadhikari SD, Shrivastava MP. Effects of oxyphenonium bromide and some antihistaminics (H1) on salivary flow in human volunteers. Indian J Physiol Pharmacol. 1997 Apr;41(2):183-4. PubMed PMID: 9142568.

7: Scholtmeijer RJ, van Mastrigt R. The effect of oxyphenonium bromide and oxybutynin hydrochloride on detrusor contractility and reflux in children with vesicoureteral reflux and detrusor instability. J Urol. 1991 Aug;146(2 ( Pt 2)):660-2. PubMed PMID: 1907331.

8: Feitsma KG. Enantiomers of oxyphenonium bromide. Analytical and pharmacological aspects. Pharm Weekbl Sci. 1988 Oct 14;10(5):221-3. PubMed PMID: 3144701.

9: Feitsma KG, Postma DS, Koëter GH, Nossent GD, Brenth BF, de Zeeuw RA. Comparative study of the bronchodilating effects of (-)- and (+)-oxyphenonium bromide. Br J Clin Pharmacol. 1988 Jun;25(6):683-7. PubMed PMID: 3144299; PubMed Central PMCID: PMC1386444.

10: Gupta B, Singh AK, Crowell SB. A comparative study of cimetidine, ranitidine & combination of ranitidine with oxyphenonium bromide in inhibition of nocturnal gastric secretion. Indian J Med Res. 1987 Nov;86:635-40. PubMed PMID: 3132427.