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MedKoo Cat#: 412865 | Name: Cifenline succinate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cifenline succinate is used for the treatment of supraventricular and ventricular arrhythmias, and in obstructive hypertrophic cardiomyopathy.

Chemical Structure

Cifenline succinate
Cifenline succinate
CAS#100678-32-8 (succinate)

Theoretical Analysis

MedKoo Cat#: 412865

Name: Cifenline succinate

CAS#: 100678-32-8 (succinate)

Chemical Formula: C22H24N2O4

Exact Mass: 380.1736

Molecular Weight: 380.44

Elemental Analysis: C, 69.46; H, 6.36; N, 7.36; O, 16.82

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 Back order
50mg USD 1,250.00 Back order
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Related CAS #
53267-01-9 (free base) 100678-32-8 (succinate)
Synonym
Cifenline succinate; Cipralan; Ritmalan
IUPAC/Chemical Name
1H-Imidazole, 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-, (+-)-, butanedioate (1:1)
InChi Key
XFUIOIWYMHEPIE-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H18N2.C4H6O4/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17;5-3(6)1-2-4(7)8/h1-10,16H,11-13H2,(H,19,20);1-2H2,(H,5,6)(H,7,8)
SMILES Code
O=C(O)CCC(O)=O.C1(C2C(C3=CC=CC=C3)(C4=CC=CC=C4)C2)=NCCN1
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 380.44 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
1: Massarella JW, Defeo TM, Liguori J, Passe S, Aogaichi K. The effects of cimetidine and ranitidine on the pharmacokinetics of cifenline. Br J Clin Pharmacol. 1991 Apr;31(4):481-3. doi: 10.1111/j.1365-2125.1991.tb05566.x. PMID: 2049259; PMCID: PMC1368338. 2: Sakane N, Onishi N, Katamura M, Sato H, Takamasu M, Yoshida T. Cifenline succinate and dementia in an elderly NIDDM patient. Diabetes Care. 1998 Feb;21(2):320-1. doi: 10.2337/diacare.21.2.320c. PMID: 9540002. 3: Nestico PF, Morganroth J, Horowitz LN. New antiarrhythmic drugs. Drugs. 1988 Mar;35(3):286-319. doi: 10.2165/00003495-198835030-00005. PMID: 3286214. 4: Kostis JB, Davis D, Kluger J, Aogaichi K, Smith M. Cifenline in the short- term treatment of patients with ventricular premature complexes: a double-blind placebo-controlled study. J Cardiovasc Pharmacol. 1989 Jul;14(1):88-95. doi: 10.1097/00005344-198907000-00016. PMID: 2475722. 5: Aoyama N, Sasaki T, Yoshida M, Suzuki K, Matsuyama K, Aizaki T, Izumi T, Kondo R, Kamijo Y, Soma K, Ohwada T. Effect of charcoal hemoperfusion on clearance of cibenzoline succinate (cifenline) poisoning. J Toxicol Clin Toxicol. 1999;37(4):505-8. doi: 10.1081/clt-100102443. PMID: 10465249. 6: Mohiuddin SM, Hee TT, Hunter CB, Hilleman DE, Sketch MH Sr. Loss of efficacy during long-term cifenline therapy: development of antiarrhythmic resistance? Ann Pharmacother. 1993 May;27(5):550-4. doi: 10.1177/106002809302700502. PMID: 8347900. 7: Touboul P. Cibenzoline [Cibenzoline]. Arch Mal Coeur Vaiss. 1985 Oct;78 Spec No:91-4. French. PMID: 3938265. 8: Majima T, Takagi C, Koike Y, Shigemoto M, Yamada T, Akagi T. [Cibenzoline- succinate-induced hypoglycemia]. Nihon Naika Gakkai Zasshi. 2004 Oct 10;93(10):2197-200. Japanese. doi: 10.2169/naika.93.2197. PMID: 15552920. 9: Ross AJ, Go MV, Casey DL, Palling DJ. Kinetics and mechanism of the hydrolysis of a 2-substituted imidazoline, cibenzoline (cifenline). J Pharm Sci. 1987 Apr;76(4):306-9. doi: 10.1002/jps.2600760409. PMID: 3598889. 10: Gachot BA, Bezier M, Cherrier JF, Daubeze J. Cibenzoline and hypoglycaemia. Lancet. 1988 Jul 30;2(8605):280. doi: 10.1016/s0140-6736(88)92570-6. PMID: 2899265. 11: Hamada M, Ikeda S, Shigematsu Y. Advances in medical treatment of hypertrophic cardiomyopathy. J Cardiol. 2014 Jul;64(1):1-10. doi: 10.1016/j.jjcc.2014.02.022. Epub 2014 Apr 13. Erratum in: J Cardiol. 2014 Oct;64(4):330. PMID: 24735741. 12: Hamada M. Cibenzoline therapy for mitral regurgitation in patients with HOCM. Intern Med. 2004 Jan;43(1):3-4. doi: 10.2169/internalmedicine.43.3. PMID: 14964571. 13: Nakagawa Y, Ishizaki M, Kozono A, Hanada K, Higashi T, Ueyama H. [A case of myasthenia-like symptoms induced by cibenzoline overdosage]. Rinsho Shinkeigaku. 2018 Jan 26;58(1):41-44. Japanese. doi: 10.5692/clinicalneurol.cn-001070. Epub 2017 Dec 22. PMID: 29269691. 14: Omae T. [Perioperative management for patients with hypertrophic cardiomyopathy]. Masui. 2014 Jan;63(1):16-21. Japanese. PMID: 24558927. 15: Vaughan Williams EM. Classifying antiarrhythmic actions: by facts or speculation. J Clin Pharmacol. 1992 Nov;32(11):964-77. doi: 10.1002/j.1552-4604.1992.tb03797.x. PMID: 1474169. 16: Manz M, Lüderitz B. Supraventricular tachycardia and pre-excitation syndromes: pharmacological therapy. Eur Heart J. 1993 Sep;14 Suppl E:91-8. doi: 10.1093/eurheartj/14.suppl_e.91. PMID: 8223763. 17: Hilleman DE, Mohiuddin SM, Ahmed IS, Dahl JM. Cibenzoline-induced hypoglycemia. Drug Intell Clin Pharm. 1987 Jan;21(1 Pt 1):38-40. doi: 10.1177/10600280870211p104. PMID: 3545736. 18: Somberg J. Antiarrhythmic drug therapy. Recent advances and current status. Cardiology. 1985;72(5-6):329-48. doi: 10.1159/000173888. PMID: 2866841. 19: Harron DW, Brogden RN, Faulds D, Fitton A. Cibenzoline. A review of its pharmacological properties and therapeutic potential in arrhythmias. Drugs. 1992 May;43(5):734-59. doi: 10.2165/00003495-199243050-00008. PMID: 1379150. 20: Houdent C, Noblet C, Vandoren C, Levesque H, Morin C, Moore N, Courtois H, Wolf LM. Hypoglycémie induite par la cibenzoline chez le sujet âgé [Hypoglycemia induced by cibenzoline in the elderly]. Rev Med Interne. 1991 Mar- Apr;12(2):143-5. French. doi: 10.1016/s0248-8663(05)81379-7. PMID: 1852997.