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MedKoo Cat#: 558194 | Name: Umespirone

Description:

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

Umespirone is a potential antipsychotic/anxiolytic drug of the azapirone class which possesses anxiolytic and antipsychotic properties.

Chemical Structure

Umespirone
Umespirone
CAS#107736-98-1

Theoretical Analysis

MedKoo Cat#: 558194

Name: Umespirone

CAS#: 107736-98-1

Chemical Formula: C28H40N4O5

Exact Mass: 512.3000

Molecular Weight: 512.65

Elemental Analysis: C, 65.60; H, 7.86; N, 10.93; O, 15.60

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Umespirone; Umespirona; Umespironum;
IUPAC/Chemical Name
3,7-Diazabicyclo(3.3.1)nonane-2,4,6,8-tetrone, 3-butyl-7-(4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)-9,9-dimethyl-
InChi Key
BXNRTMZZILHVNJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H40N4O5/c1-5-6-14-31-24(33)22-26(35)32(27(36)23(25(31)34)28(22,2)3)15-10-9-13-29-16-18-30(19-17-29)20-11-7-8-12-21(20)37-4/h7-8,11-12,22-23H,5-6,9-10,13-19H2,1-4H3
SMILES Code
O=C(N(CCCC)C(C1C(N2CCCCN3CCN(C4=CC=CC=C4OC)CC3)=O)=O)C(C1(C)C)C2=O
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 512.65 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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Hemodynamic, antiischemic, and neurohumoral effects of tedisamil and atenolol in patients with coronary artery disease. Cardiovasc Drugs Ther. 2000 Oct;14(5):511-21. PubMed PMID: 11101199. 5: Barrett TD, Hennan JK, Fischbach PS, O'Neill BP, Driscoll EM Jr, Lucchesi BR. Tedisamil and dofetilide-induced torsades de pointes, rate and potassium dependence. Br J Pharmacol. 2001 Apr;132(7):1493-500. PubMed PMID: 11264243; PubMed Central PMCID: PMC1572702. 6: Doggrell SA, Nand V. Effects of tedisamil on cardiovascular tissues isolated from normo- and hypertensive rats. J Cardiovasc Pharmacol Ther. 2001 Jul;6(3):261-72. PubMed PMID: 11584333. 7: Church J, McLarnon JG. Tedisamil blocks BK-type Ca(2+)-dependent K(+) channels and modulates action potentials in rat hippocampal neurons. Neurosci Lett. 2002 Feb 15;319(2):79-82. PubMed PMID: 11825675. 8: Fischbach PS, Barrett TD, Goyal R, Tran BC, Syed ZA, Hennan JK, Lucchesi BR. Conversion of atrial fibrillation by the experimental antiarrhythmic drug tedisamil in two canine models. J Cardiovasc Electrophysiol. 2001 Oct;12(10):1138-44. PubMed PMID: 11699522. 9: Freestone B, Lip GY. Tedisamil: a new novel antiarrhythmic. Expert Opin Investig Drugs. 2004 Feb;13(2):151-60. PubMed PMID: 14996649. 10: Beatch GN, Abraham S, MacLeod BA, Yoshida NR, Walker MJ. Antiarrhythmic properties of tedisamil (KC8857), a putative transient outward K+ current blocker. Br J Pharmacol. 1991 Jan;102(1):13-8. PubMed PMID: 2043919; PubMed Central PMCID: PMC1917915. 11: Sarraf G, Barrett TD, Walker MJ. Tedisamil and lidocaine enhance each other's antiarrhythmic activity against ischaemia-induced arrhythmias in rats. Br J Pharmacol. 2003 Aug;139(8):1389-98. PubMed PMID: 12922925; PubMed Central PMCID: PMC1573972. 12: Dukes ID, Cleemann L, Morad M. Tedisamil blocks the transient and delayed rectifier K+ currents in mammalian cardiac and glial cells. J Pharmacol Exp Ther. 1990 Aug;254(2):560-9. PubMed PMID: 2384886. 13: Hayes E, Courtice ID, Abraham S, Walker MJ. Acute toxicity of tedisamil, a new potassium channel blocking drug. Pharmacol Toxicol. 1993 Nov;73(5):257-61. PubMed PMID: 8115307. 14: Krishnamoorthy S, Lip GY. Novel antiarrhythmic drugs in atrial fibrillation: focus on tedisamil. Expert Opin Investig Drugs. 2009 Aug;18(8):1191-6. doi: 10.1517/13543780903114150. Review. PubMed PMID: 19604120. 15: Bril A, Landais L, Gout B. Actions and interactions of E-4031 and tedisamil on reperfusion-induced arrhythmias and QT interval in rat in vivo. Cardiovasc Drugs Ther. 1993 Apr;7(2):233-40. PubMed PMID: 8357777. 16: Radicke S, Cotella D, Sblattero D, Ravens U, Santoro C, Wettwer E. The transmembrane beta-subunits KCNE1, KCNE2, and DPP6 modify pharmacological effects of the antiarrhythmic agent tedisamil on the transient outward current Ito. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jun;379(6):617-26. doi: 10.1007/s00210-008-0389-1. Epub 2009 Jan 20. PubMed PMID: 19153714. 17: Turcani M, Thormaehlen D, Rupp H. Tedisamil attenuates foetal transformation of myosin in the hypertrophied rat myocardium. Br J Pharmacol. 2004 Nov;143(5):561-72. Epub 2004 Oct 4. PubMed PMID: 15466442; PubMed Central PMCID: PMC1575437. 18: Wettwer E, Himmel HM, Amos GJ, Li Q, Metzger F, Ravens U. Mechanism of block by tedisamil of transient outward current in human ventricular subepicardial myocytes. Br J Pharmacol. 1998 Oct;125(4):659-66. PubMed PMID: 9831899; PubMed Central PMCID: PMC1571017. 19: Mitrovic V, Oehm E, Strasser R, Schlepper M, Pitschner HF. [The new potassium channel blocker tedisamil and its hemodynamic, anti-ischemic and neurohumoral effect in patients with coronary heart disease]. Z Kardiol. 1996 Dec;85(12):961-72. German. PubMed PMID: 9082675. 20: Seki S, Tribulova N, Manoach M, Mochizuki S. Modulation of intracellular Ca(2+) concentration by tedisamil, a class III antiarrhythmic agent, in isolated heart preparation. Life Sci. 2003 Aug 22;73(14):1805-11. PubMed PMID: 12888119. 1: Holland RL, Wesnes K, Dietrich B. Single dose human pharmacology of umespirone. Eur J Clin Pharmacol. 1994;46(5):461-8. PubMed PMID: 7957544. 2: Barnes NM, Costall B, Domeney AM, Gerrard PA, Kelly ME, Krähling H, Naylor RJ, Tomkins DM, Williams TJ. The effects of umespirone as a potential anxiolytic and antipsychotic agent. Pharmacol Biochem Behav. 1991 Sep;40(1):89-96. PubMed PMID: 1685786. 3: Itzhak Y, Ruhland M, Krähling H. Binding of umespirone to the sigma receptor: evidence for multiple affinity states. Neuropharmacology. 1990 Feb;29(2):181-4. PubMed PMID: 1970425. 4: Schmidt WJ, Krähling H, Ruhland M. Antagonism of AP-5-induced sniffing stereotypy links umespirone to atypical antipsychotics. Life Sci. 1991;48(6):499-505. PubMed PMID: 1671523. 5: Ahlenius S, Wijkström A. Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat. Eur J Pharmacol. 1992 Nov 3;222(1):69-74. PubMed PMID: 1361441. 6: Schmidt J, Borchers F. Thermospray tandem mass spectrometric (TS MS-MS) investigation of the main metabolite of umespirone (KC-9172). Biol Mass Spectrom. 1992 Nov;21(11):610-3. PubMed PMID: 1360818. 7: Krähling H, Fuchs A, Ruhland M, Schön U, Mol F, Tulp M. KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. II. Discrimination from typical neuroleptics and benzodiazepine-like minor tranquilizers. Pharmacopsychiatry. 1988 Nov;21(6):399-401. PubMed PMID: 2907650. 8: Ruhland M, Krähling H, Fuchs A, Schön U. KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. I. Antipsychotic and anxiolytic activity in comparison with chlorpromazine, clozapine, diazepam and buspirone. Pharmacopsychiatry. 1988 Nov;21(6):396-8. PubMed PMID: 2907649. 9: De Beun R, Rijk HW, Broekkamp CL. Cross-familiarisation conditioned taste aversion procedure as a method to reveal stimulus resemblance between drugs: studies on the 5-HT1A agonist 8-OHDPAT. Psychopharmacology (Berl). 1993;112(1):121-8. PubMed PMID: 7871000.

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