Synonym
Ciclotropium (free base); Ciclotropium ion; iclotropium cation; UNII-S28PG9706T
IUPAC/Chemical Name
(1R,3r,5S)-3-(2-cyclopentyl-2-phenylacetoxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium
InChi Key
WNMNMBROVJBYLM-GJSXJBKHSA-N
InChi Code
InChI=1S/C24H36NO2/c1-17(2)25(3)20-13-14-21(25)16-22(15-20)27-24(26)23(19-11-7-8-12-19)18-9-5-4-6-10-18/h4-6,9-10,17,19-23H,7-8,11-16H2,1-3H3/q+1/t20-,21+,22+,23?,25?
SMILES Code
CC([N+]1([C@@H]2CC[C@H]1C[C@@H](OC(C(c3ccccc3)C4CCCC4)=O)C2)C)C
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
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
370.56
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.
| 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 |
1: Heuer H, Frenking B, Thale J, Gülker H, Müller US, Bender F. Effects of the new vagolytic compound ciclotropium bromide on heart rate and atrial vulnerability. Arzneimittelforschung. 1986 Oct;36(10):1451-4. PMID: 2434105.
2: Liebmann B, Mayer S, Mutschler E, Spahn-Langguth H. Studies on the metabolic clearance of ciclotropium to alpha-phenylciclopentylacetic acid using a new enantiospecific metabolite assay. Arzneimittelforschung. 1992 Nov;42(11):1354-8. PMID: 1492851.
3: Glube N, Closs E, Langguth P. OCTN2-mediated carnitine uptake in a newly discovered human proximal tubule cell line (Caki-1). Mol Pharm. 2007 Jan- Feb;4(1):160-8. doi: 10.1021/mp060073a. PMID: 17274673.
4: Liebmann B, Henke D, Spahn-Langguth H, Mutschler E. Determination of the quaternary compound ciclotropium in human biological material after hydrolysis and derivatization with the fluorophor flunoxaprofen chloride. J Chromatogr. 1991 Dec 6;572(1-2):181-93. doi: 10.1016/0378-4347(91)80482-r. PMID: 1818053.
5: Brandstätter G, Kratochvil P, Stupnicki T, Zenker G. Die Wirkung von Ciclotropiumbromid auf den Druck im menschlichen Gallengangsystem [Effect of ciclotropium bromide on pressure in the human common bile duct]. Arzneimittelforschung. 1983;33(12):1691-3. German. PMID: 6686777.
6: Ding RW, Port RE, Ortmann K, Liebmann B, Spahn-Langguth H, Mutschler E, Weber E. The effect of ciclotropium on human heart rate. Eur J Clin Pharmacol. 1994;46(5):455-9. doi: 10.1007/BF00191911. PMID: 7957543.
7: Lepsien G, Buck W. Doppelblindstudie zur Wirkung von Ciclotropiumbromid auf die glatte Muskulatur des Osophagus. Darstellung eines Tests zur spasmolytischen Wirksamkeit [Double-blind study of the effect of cyclotropium bromide on the smooth musculature of the esophagus. Description of a test of spasmolytic action]. Arzneimittelforschung. 1988 Jul;38(7):927-31. German. PMID: 3207438.
