Fadolmidine HCl

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

MedKoo CAT#: 510216

CAS#: 189353-32-0(Fadolmidine HCl); 189353-31-9(Fadolmidine free base)

Description: Fadolmidine, also known as MPV-2426, is a novel and potent alpha2 -adrenoceptor (alpha2) -AR) agonist developed for spinal analgesia. Fadolmidine displayed high affinity and full agonist efficacy at all three human alpha2-adrenoceptor subtypes (A, B and C) in transfected CHO cells with EC50 values (nM) of 0.4, 4.9 and 0.5, respectively. Fadolmidine inhibited also electrically evoked contractions in rat vas deferens demonstrating the activation of rodent presynaptic alpha2D-adrenoceptors with an EC50 value of 6.4 nM. Moreover, fadolmidine was a full agonist at human alpha1A-adrenoreceptor (EC50 value 22 nM) and alpha1B-adrenoreceptor (EC50 value 3.4 nM) in human LNCaP cells and transfected HEK cells, respectively. Agonism at the alpha1-adrenoceptor was also observed in rat vas deferens preparations although at lower potency (EC50 value 5.6 microM). Fadolmidine demonstrated potent alpha2-adrenoceptor agonist activity also in vivo by inhibiting electrically induced tachycardia in pithed rats and increasing mean arterial pressure in anaesthetised rats. However, after systemic administration, fadolmidine had considerably weaker CNS-mediated effects (mydriasis and sedation) compared to dexmedetomidine possibly due to limited penetration through the blood brain barrier by fadolmidine . In a conclusion, fadolmidine is a potent full agonist at all three alpha2-adrenoceptor subtypes with a pharmacological profile compatible with a therapeutic value e.g. after spinal administration. (Eur J Pharmacol. 2008 Dec 3;599(1-3):65-71.)


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Fadolmidine HCl is not in stock, but 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#: 510216
Name: Fadolmidine HCl
CAS#: 189353-32-0(Fadolmidine HCl); 189353-31-9(Fadolmidine free base)
Chemical Formula: C13H15ClN2O
Exact Mass:
Molecular Weight: 250.72
Elemental Analysis: C, 62.28; H, 6.03; Cl, 14.14; N, 11.17; O, 6.38


Synonym: Fadolmidine; MPV2426; MPV-2426; MPV 2426

IUPAC/Chemical Name: 3-((1H-imidazol-4-yl)methyl)-2,3-dihydro-1H-inden-5-ol hydrochloride

InChi Key: OYKZVKWXOWICFI-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H14N2O.ClH/c16-12-4-3-9-1-2-10(13(9)6-12)5-11-7-14-8-15-11;/h3-4,6-8,10,16H,1-2,5H2,(H,14,15);1H

SMILES Code: OC1=CC2=C(CCC2CC3=CNC=N3)C=C1.[H]Cl


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:
>5 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


Additional Information

Related CAS#
189353-31-9(Fadolmidine free base)


References

1: Berg T. Angiotensin AT1 - α2C-Adrenoceptor Interaction Disturbs α2A-auto-Inhibition of Catecholamine Release in Hypertensive Rats. Front Neurol. 2013 Jun 10;4:70. doi: 10.3389/fneur.2013.00070. PubMed PMID: 23772221; PubMed Central PMCID: PMC3677154.

2: Wei H, Pertovaara A. Regulation of neuropathic hypersensitivity by α(2) -adrenoceptors in the pontine A7 cell group. Basic Clin Pharmacol Toxicol. 2013 Feb;112(2):90-5. doi: 10.1111/j.1742-7843.2012.00930.x. Epub 2012 Sep 25. PubMed PMID: 22900496.

3: Chan AK, Cheung CW, Chong YK. Alpha-2 agonists in acute pain management. Expert Opin Pharmacother. 2010 Dec;11(17):2849-68. doi: 10.1517/14656566.2010.511613. Epub 2010 Aug 13. Review. PubMed PMID: 20707597.

4: Leino T, Viitamaa T, Haapalinna A, Lehtimäki J, Virtanen R. Pharmacological profile of intrathecal fadolmidine, a alpha2-adrenoceptor agonist, in rodent models. Naunyn Schmiedebergs Arch Pharmacol. 2009 Dec;380(6):539-50. doi: 10.1007/s00210-009-0460-6. Epub 2009 Oct 14. PubMed PMID: 19826791.

5: Lehtimäki J, Leino T, Koivisto A, Viitamaa T, Lehtimäki T, Haapalinna A, Kuokkanen K, Virtanen R. In vitro and in vivo profiling of fadolmidine, a novel potent alpha(2)-adrenoceptor agonist with local mode of action. Eur J Pharmacol. 2008 Dec 3;599(1-3):65-71. doi: 10.1016/j.ejphar.2008.10.003. Epub 2008 Oct 9. PubMed PMID: 18930723.

6: Pertovaara A, Wei H. Dual influence of the striatum on neuropathic hypersensitivity. Pain. 2008 Jul;137(1):50-9. Epub 2007 Sep 17. PubMed PMID: 17870240.

7: Ansah OB, Pertovaara A. Peripheral suppression of arthritic pain by intraarticular fadolmidine, an alpha 2-adrenoceptor agonist, in the rat. Anesth Analg. 2007 Jul;105(1):245-50. PubMed PMID: 17578982.

8: Smith H, Elliott J. Alpha(2) receptors and agonists in pain management. Curr Opin Anaesthesiol. 2001 Oct;14(5):513-8. PubMed PMID: 17019139.

9: Niemi R, Huuskonen J, Laine K, Järvinen T. Synthesis, hydrolysis, and intraocular pressure lowering effects of fadolmidine prodrugs. Int J Pharm. 2005 May 13;295(1-2):121-7. PubMed PMID: 15847997.

10: Savolainen J, Niemi R, Mäntylä A, Huuskonen J, Järvinen T. Fadolmidine-induced ocular hypotension in normotensive rabbits. J Pharm Pharmacol. 2005 Feb;57(2):191-5. PubMed PMID: 15720782.