Zamifenacin

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

MedKoo CAT#: 526580

CAS#: 127308-82-1

Description: Zamifenacin, also known as UK-76654, is a potent gut M3 selective muscarinic antagonist, reduces colonic motor activity in patients with irritable bowel syndrome.


Price and Availability

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Zamifenacin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526580
Name: Zamifenacin
CAS#: 127308-82-1
Chemical Formula: C27H29NO3
Exact Mass: 415.2147
Molecular Weight: 415.533
Elemental Analysis: C, 78.04; H, 7.03; N, 3.37; O, 11.55


Synonym: UK 76654; UK76654; UK-76654; Zamifenacin

IUPAC/Chemical Name: (R)-3-(benzhydryloxy)-1-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)piperidine

InChi Key: BDNFQGRSKSQXRI-XMMPIXPASA-N

InChi Code: InChI=1S/C27H29NO3/c1-3-8-22(9-4-1)27(23-10-5-2-6-11-23)31-24-12-7-16-28(19-24)17-15-21-13-14-25-26(18-21)30-20-29-25/h1-6,8-11,13-14,18,24,27H,7,12,15-17,19-20H2/t24-/m1/s1

SMILES Code: N1(CCC2=CC(OCO3)=C3C=C2)C[C@H](OC(C4=CC=CC=C4)C5=CC=CC=C5)CCC1


Technical Data

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).

Harmonized System Code:
293490


References

1: Houghton LA, Rogers J, Whorwell PJ, Campbell FC, Williams NS, Goka J. Zamifenacin (UK-76, 654) a potent gut M3 selective muscarinic antagonist, reduces colonic motor activity in patients with irritable bowel syndrome. Aliment Pharmacol Ther. 1997 Jun;11(3):561-8. PubMed PMID: 9218083.

2: Amacher DE, Fasulo LM, Charuel C, Comby P, Beaumont K. In vitro toxicity of zamifenacin (UK-76,654) and metabolites in primary hepatocyte cultures. Xenobiotica. 1998 Sep;28(9):895-908. PubMed PMID: 9764931.

3: Watson N, Reddy H, Stefanich E, Eglen RM. Characterization of the interaction of zamifenacin at muscarinic receptors in vitro. Eur J Pharmacol. 1995 Oct 16;285(2):135-42. PubMed PMID: 8566131.

4: Beaumont KC, Causey AG, Coates PE, Smith DA. Pharmacokinetics and metabolism of zamifenacin in mouse, rat, dog and man. Xenobiotica. 1996 Apr;26(4):459-71. PubMed PMID: 9173686.

5: Hughes T, Wright AR, Owen JP, Keir MJ. Computerized planimetry in the objective assessment of the antispasmodic effect of Zamifenacin in double contrast barium enemas. Br J Radiol. 1996 Apr;69(820):301-5. PubMed PMID: 8665128.

6: Barlow RB, Bond SM, Branthwaite AG, Jackson O, McQueen DS, Smith KM, Smith PJ. Selective blockade of M2 and M3 muscarinic receptors by hexahydrobenzyl-fourdapine and a comparison with zamifenacin. Br J Pharmacol. 1995 Dec;116(7):2897-902. PubMed PMID: 8680722; PubMed Central PMCID: PMC1909210.

7: Golding JF, Stott JR. Comparison of the effects of a selective muscarinic receptor antagonist and hyoscine (scopolamine) on motion sickness, skin conductance and heart rate. Br J Clin Pharmacol. 1997 Jun;43(6):633-7. PubMed PMID: 9205824; PubMed Central PMCID: PMC2042789.

8: Wallis RM. Pre-clinical and clinical pharmacology of selective muscarinic M3 receptor antagonists. Life Sci. 1995;56(11-12):861-8. PubMed PMID: 10188786.

9: Zholos AV, Bolton TB. Muscarinic receptor subtypes controlling the cationic current in guinea-pig ileal smooth muscle. Br J Pharmacol. 1997 Nov;122(5):885-93. PubMed PMID: 9384504; PubMed Central PMCID: PMC1564999.

10: Cossy J. Selective methodologies for the synthesis of biologically active piperidinic compounds. Chem Rec. 2005;5(2):70-80. Review. PubMed PMID: 15825169.

11: Boyd DF, Millar JA, Watkins CS, Mathie A. The role of Ca2+ stores in the muscarinic inhibition of the K+ current IK(SO) in neonatal rat cerebellar granule cells. J Physiol. 2000 Dec 1;529 Pt 2:321-31. PubMed PMID: 11101643; PubMed Central PMCID: PMC2270195.

12: Choppin A, Eglen RM, Hegde SS. Pharmacological characterization of muscarinic receptors in rabbit isolated iris sphincter muscle and urinary bladder smooth muscle. Br J Pharmacol. 1998 Jul;124(5):883-8. PubMed PMID: 9692772; PubMed Central PMCID: PMC1565469.

13: Preiksaitis HG, Laurier LG. Pharmacological and molecular characterization of muscarinic receptors in cat esophageal smooth muscle. J Pharmacol Exp Ther. 1998 May;285(2):853-61. PubMed PMID: 9580636.

14: Watson N, Magnussen H, Rabe KF. Pharmacological characterization of the muscarinic receptor subtype mediating contraction of human peripheral airways. J Pharmacol Exp Ther. 1995 Sep;274(3):1293-7. PubMed PMID: 7562501.

15: Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I. Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. PubMed PMID: 10374898.

16: Lin S, Kajimura M, Takeuchi K, Kodaira M, Hanai H, Kaneko E. Expression of muscarinic receptor subtypes in rat gastric smooth muscle: effect of M3 selective antagonist on gastric motility and emptying. Dig Dis Sci. 1997 May;42(5):907-14. PubMed PMID: 9149041.

17: Ahfat NM, Buckton G, Burrows R, Ticehurst MD. An exploration of inter-relationships between contact angle, inverse phase gas chromatography and triboelectric charging data. Eur J Pharm Sci. 2000 Jan;9(3):271-6. PubMed PMID: 10594384.

18: Choppin A. Muscarinic receptors in isolated urinary bladder smooth muscle from different mouse strains. Br J Pharmacol. 2002 Oct;137(4):522-8. PubMed PMID: 12359634; PubMed Central PMCID: PMC1573519.

19: Choppin A, Eglen RM. Pharmacological characterization of muscarinic receptors in mouse isolated urinary bladder smooth muscle. Br J Pharmacol. 2001 Aug;133(7):1035-40. PubMed PMID: 11487513; PubMed Central PMCID: PMC1572871.

20: Dunphy RC, Verne GN. Drug treatment options for irritable bowel syndrome: managing for success. Drugs Aging. 2001;18(3):201-11. Review. PubMed PMID: 11302287.