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MedKoo Cat#: 326927 | Name: Cizolirtine citrate

Description:

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

Cizolirtine, also known as E-4018 (citrate salt) or E-3710, is a calcitonin gene-related peptide antagonist potentially for the treatment of pain, overactive. The efficacy of Cizolirtine has been demonstrated in various models of acute and inflammatory pain in rodents. Cizolirtine may be useful for alleviating some neuropathic somatosensory disorders, in particular cold allodynia, with a reduced risk of undesirable side effects.. Cizolirtine inhibits the spinal release of substance P and CGRP in rats.

Chemical Structure

Cizolirtine citrate
Cizolirtine citrate
CAS#251375-82-3 (citrate)

Theoretical Analysis

MedKoo Cat#: 326927

Name: Cizolirtine citrate

CAS#: 251375-82-3 (citrate)

Chemical Formula: C21H29N3O8

Exact Mass:

Molecular Weight: 451.48

Elemental Analysis: C, 55.87; H, 6.47; N, 9.31; O, 28.35

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 #
142155-43-9 (free base) 251375-82-3 (citrate)
Synonym
Cizolirtine citrate; E-4018; E4018; E 4018
IUPAC/Chemical Name
N,N-dimethyl-2-((1-methyl-1H-pyrazol-5-yl)(phenyl)methoxy)ethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate
InChi Key
JLKUMSHHQYQLSG-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H21N3O.C6H8O7/c1-17(2)11-12-19-15(13-7-5-4-6-8-13)14-9-10-16-18(14)3;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-10,15H,11-12H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
SMILES Code
CN1N=CC=C1C(C2=CC=CC=C2)OCCN(C)C.O=C(CC(C(O)=O)(O)CC(O)=O)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
Related CAS# 142155-43-9(Cizolirtine free base) 251375-82-3 (Cizolirtine citrate or E-4018)

Preparing Stock Solutions

The following data is based on the product molecular weight 451.48 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: Costantini E, Lazzeri M. Editorial comment on: Cizolirtine citrate is safe and effective for treating urinary incontinence secondary to overactive bladder: a phase 2 proof-of-concept study. Eur Urol. 2010 Jan;57(1):152-3. doi: 10.1016/j.eururo.2009.04.046. Epub 2009 May 7. PubMed PMID: 19446952. 2: Zát'ura F, Vsetica J, Abadías M, Pavlík I, Schraml P, Brod'ák M, Villoria J, Sust M; E-4018/CL50 Study Group. Cizolirtine citrate is safe and effective for treating urinary incontinence secondary to overactive bladder: a phase 2 proof-of-concept study. Eur Urol. 2010 Jan;57(1):145-52. doi: 10.1016/j.eururo.2009.04.045. Epub 2009 May 7. PubMed PMID: 19446951. 3: Soljanik I. Editorial comment on: Cizolirtine citrate is safe and effective to treat urinary incontinence secondary to overactive bladder: a phase 2 proof-of-concept study. Eur Urol. 2010 Jan;57(1):153. doi: 10.1016/j.eururo.2009.04.047. Epub 2009 May 7. PubMed PMID: 19446950. 4: Martínez-García R, Abadías M, Arañó P, Perales L, Ruíz JL, Sust M, Conejero J; ESCLIN 006/00 study group. Cizolirtine citrate, an effective treatment for symptomatic patients with urinary incontinence secondary to overactive bladder: a pilot dose-finding study. Eur Urol. 2009 Jul;56(1):184-90. doi: 10.1016/j.eururo.2008.04.027. Epub 2008 Apr 18. PubMed PMID: 18485575. 5: Lazzeri M. Editorial comment on: Cizolirtine citrate, an effective treatment for symptomatic patients with urinary incontinence secondary to overactive bladder: a pilot dose-finding study. Eur Urol. 2009 Jul;56(1):191-2. doi: 10.1016/j.eururo.2008.04.029. Epub 2008 Apr 18. PubMed PMID: 18485574. 6: May F, Bauer R. Editorial comment on: Cizolirtine citrate, an effective treatment for symptomatic patients with urinary incontinence secondary to overactive bladder: a pilot dose-finding study. Eur Urol. 2009 Jul;56(1):191. doi: 10.1016/j.eururo.2008.04.028. Epub 2008 Apr 18. PubMed PMID: 18485571. 7: Aubel B, Kayser V, Farré A, Hamon M, Bourgoin S. Evidence for adenosine- and serotonin-mediated antihyperalgesic effects of cizolirtine in rats suffering from diabetic neuropathy. Neuropharmacology. 2007 Feb;52(2):487-96. Epub 2006 Oct 5. PubMed PMID: 17027046. 8: Aboul-Enein HY, Ali I. Enantiomeric separation of cizolirtine and metabolites on amylose tris (3,5-dimethylphenyl carbamate) chiral stationary phase. Farmaco. 2004 Sep;59(9):743-6. PubMed PMID: 15337441. 9: Pavlik I, Suchy J, Pacík D, Bokr R, Sust M, Villoria J, Abadías M; Evaluation of Cizolirtine Citrate to Treat Renal Colic Pain Study Group. Comparison of cizolirtine citrate and metamizol sodium in the treatment of adult acute renal colic: a randomized, double-blind, clinical pilot study. Clin Ther. 2004 Jul;26(7):1061-72. PubMed PMID: 15336471. 10: Aubel B, Kayser V, Mauborgne A, Farré A, Hamon M, Bourgoin S. Antihyperalgesic effects of cizolirtine in diabetic rats: behavioral and biochemical studies. Pain. 2004 Jul;110(1-2):22-32. PubMed PMID: 15275748. 11: Kayser V, Farré A, Hamon M, Bourgoin S. Effects of the novel analgesic, cizolirtine, in a rat model of neuropathic pain. Pain. 2003 Jul;104(1-2):169-77. PubMed PMID: 12855326. 12: Gómez-Gomar A, Ortega E, Calvet C, Mercé R, Frigola J. Simultaneous separation of the enantiomers of cizolirtine and its degradation products by capillary electrophoresis. J Chromatogr A. 2002 Mar 15;950(1-2):257-70. PubMed PMID: 11991000. 13: Shembalkar P, Täubel J, Abadias M, Arezina R, Hammond K, Anand P. Cizolirtine citrate (E-4018) in the treatment of chronic neuropathic pain. Curr Med Res Opin. 2001;17(4):262-6. PubMed PMID: 11922399. 14: Monck N. Cizolirtine. Laboratorios Dr Esteve. Curr Opin Investig Drugs. 2001 Sep;2(9):1269-72. Review. PubMed PMID: 11717814. 15: Ballet S, Aubel B, Mauborgne A, Poliénor H, Farré A, Cesselin F, Hamon M, Bourgoin AS. The novel analgesic, cizolirtine, inhibits the spinal release of substance P and CGRP in rats. Neuropharmacology. 2001 Mar;40(4):578-89. PubMed PMID: 11249967. 16: Alvarez I, Andreu F, Buxens J, Colombo M, Dordal A, Fort M, Gutiérrez B, Farré AJ. Pharmacology of cizolirtine: a new analgesic agent. Methods Find Exp Clin Pharmacol. 2000 May;22(4):211-21. PubMed PMID: 10939032. 17: Matthew IR, Ogden GR, Frame JW, Wight AJ. Dose response and safety of cizolirtine citrate (E-4018) in patients with pain following extraction of third molars. Curr Med Res Opin. 2000;16(2):107-14. PubMed PMID: 10893654. 18: Martínez L, Serafini MT, Pretel MJ, Garcia-Soret A, Moragon T, Puig S. Absorption, distribution, metabolism and excretion of cizolirtine, a new analgesic compound, in rat and dog. Xenobiotica. 1999 Aug;29(8):859-71. PubMed PMID: 10553726. 19: Redondo J, Blázquez MA, Torrens A. Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes. Chirality. 1999;11(9):694-700. PubMed PMID: 10506430.