Moxonidine | CAS#75438-57-2 | Antihypertensive

MedKoo Cat#: 584133 | Name: Moxonidine

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Description:

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

Moxonidine is a centrally acting antihypertensive drug that is selective agonist at the imidazoline receptor subtype 1 (I1). This receptor subtype is found in both the rostral ventro-lateral pressor and ventromedial depressor areas of the medulla oblongata. Moxonidine therefore causes a decrease in sympathetic nervous system activity and a decrease in blood pressure. Moxonidine may also promote sodium excretion, improve insulin resistance and glucose tolerance and protect against hypertensive target organ damage, such as kidney disease and cardiac hypertrophy.

Chemical Structure

Moxonidine

CAS#75438-57-2 (free base)

Theoretical Analysis

MedKoo Cat#: 584133

Name: Moxonidine

CAS#: 75438-57-2 (free base)

Chemical Formula: C9H12ClN5O

Exact Mass: 241.0730

Molecular Weight: 241.68

Elemental Analysis: C, 44.73; H, 5.00; Cl, 14.67; N, 28.98; O, 6.62

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 650.00
250mg	USD 1,450.00

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Related CAS #

75438-58-3 (HCl) 75438-57-2 (free base)

Synonym

Moxonidine; Cynt; Nucynt; BE 5895; BE-5895; BE5895

IUPAC/Chemical Name

4-Chloro-5-(2-imidazolin-2-ylamino)-6-methoxy-2-methylpyrimidine

InChi Key

WPNJAUFVNXKLIM-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H12ClN5O/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9/h3-4H2,1-2H3,(H2,11,12,15)

SMILES Code

CC1=NC(OC)=C(NC2=NCCN2)C(Cl)=N1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Moxonidine (BDF5895) is a selective agonist at the imidazoline receptor subtype 1, used as antihypertensive agent.

In vitro activity:

To induce MetS (metabolic syndrome), rats were fed 3 % salt in their diet and 10 % fructose in their drinking water for 12 weeks. MetS-rats were given either moxonidine (6 mg/kg/day, gavage), efaroxan (I1R antagonist, 0.6 mg/kg/day, i.p), both treatments, or vehicles for the last two weeks. Moxonidine significantly ameliorated MetS-induced metabolic and hemodynamic derangements and the associated cardiac pathology. Moxonidine restored NR4A2 and p53 myocardial levels and enhanced autophagic flux via modulating SQSTM1/p62, LC3, and Beclin-1. Reference: Life Sci. 2023 Jan 1;312:121210. https://pubmed.ncbi.nlm.nih.gov/36410408/

In vivo activity:

In this study, airway vagal preganglionic neurons (AVPNs) were retrogradely labeled in neonatal rats from the intrathoracic trachea; retrogradely labeled AVPNs in the external formation of the nucleus ambiguus (NA) were identified in rhythmically active medullary slices using whole-cell patch-clamp techniques; and the effects of moxonidine on the spontaneous excitatory postsynaptic currents (EPSCs) of AVPNs were observed at synaptic level. The results show that moxonidine (10 μmol·L-1) significantly inhibited the frequency of spontaneous EPSCs in both inspiratory-activated and inspiratory-inhibited AVPNs. Reference: Life Sci. 2023 Jan 1;312:121210. https://pubmed.ncbi.nlm.nih.gov/32007398/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	82.75
	DMSO	21.3	88.27
	Ethanol	6.0	24.83
	PBS (pH 7.2)	2.0	8.28

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 241.68 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.

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

Formulation protocol:

1. Wang Y, Nguyen DT, Anesi J, Alramahi A, Witting PK, Chai Z, Khan AW, Kelly J, Denton KM, Golledge J. Moxonidine Increases Uptake of Oxidised Low-Density Lipoprotein in Cultured Vascular Smooth Muscle Cells and Inhibits Atherosclerosis in Apolipoprotein E-Deficient Mice. Int J Mol Sci. 2023 Feb 14;24(4):3857. doi: 10.3390/ijms24043857. PMID: 36835270; PMCID: PMC9960795. 2. Zhou X, He D, Yan X, Chen X, Li R, Zhang G, Wang J. Moxonidine inhibits excitatory inputs to airway vagal preganglionic neurons via activation of both α2-adrenoceptors and imidazoline I1 receptors. Brain Res. 2020 Apr 1;1732:146695. doi: 10.1016/j.brainres.2020.146695. Epub 2020 Jan 31. PMID: 32007398. 3. El-Sayed SS, Rezq S, Alsemeh AE, Mahmoud MF. Moxonidine ameliorates cardiac injury in rats with metabolic syndrome by regulating autophagy. Life Sci. 2023 Jan 1;312:121210. doi: 10.1016/j.lfs.2022.121210. Epub 2022 Nov 18. PMID: 36410408. 4. Zhang W, Li X, Liu Y, Chen H, Gong J. Activation of imidazoline I1 receptor by moxonidine regulates the progression of liver fibrosis in the Nrf2-dependent pathway. Biomed Pharmacother. 2017 Jun;90:821-834. doi: 10.1016/j.biopha.2017.04.025. Epub 2017 Apr 20. PMID: 28437886.

In vitro protocol:

In vivo protocol:

1. El-Sayed SS, Rezq S, Alsemeh AE, Mahmoud MF. Moxonidine ameliorates cardiac injury in rats with metabolic syndrome by regulating autophagy. Life Sci. 2023 Jan 1;312:121210. doi: 10.1016/j.lfs.2022.121210. Epub 2022 Nov 18. PMID: 36410408. 2. Zhang W, Li X, Liu Y, Chen H, Gong J. Activation of imidazoline I1 receptor by moxonidine regulates the progression of liver fibrosis in the Nrf2-dependent pathway. Biomed Pharmacother. 2017 Jun;90:821-834. doi: 10.1016/j.biopha.2017.04.025. Epub 2017 Apr 20. PMID: 28437886.

1: Kawada T, Shimizu S, Yamamoto H, Miyamoto T, Shishido T, Sugimachi M. Peripheral versus central effect of intravenous moxonidine on rat carotid sinus baroreflex-mediated sympathetic arterial pressure regulation. Life Sci. 2017 Dec 1;190:103-109. doi: 10.1016/j.lfs.2017.09.038. Epub 2017 Sep 28. PubMed PMID: 28964815. 2: Fouda MA, El-Sayed SS, Abdel-Rahman AA. Restoration of rostral ventrolateral medulla cystathionine-γ lyase activity underlies moxonidine-evoked neuroprotection and sympathoinhibition in diabetic rats. J Pharmacol Exp Ther. 2017 Nov 13. pii: jpet.117.243865. doi: 10.1124/jpet.117.243865. [Epub ahead of print] PubMed PMID: 29133386. 3: Lambert EA, Sari CI, Eikelis N, Phillips SE, Grima M, Straznicky NE, Dixon JB, Esler M, Schlaich MP, Head GA, Lambert GW. Effects of Moxonidine and Low-Calorie Diet: Cardiometabolic Benefits from Combination of Both Therapies. Obesity (Silver Spring). 2017 Nov;25(11):1894-1902. doi: 10.1002/oby.21962. Epub 2017 Sep 2. PubMed PMID: 28865109. 4: Rubio-Beltrán E, Labastida-Ramírez A, Hernández-Abreu O, MaassenVanDenBrink A, Villalón CM. Pharmacological analysis of the inhibition produced by moxonidine and agmatine on the vasodepressor sensory CGRPergic outflow in pithed rats. Eur J Pharmacol. 2017 Oct 5;812:97-103. doi: 10.1016/j.ejphar.2017.07.020. Epub 2017 Jul 8. PubMed PMID: 28694067. 5: Zhang W, Li X, Liu Y, Chen H, Gong J. Activation of imidazoline I(1) receptor by moxonidine regulates the progression of liver fibrosis in the Nrf2-dependent pathway. Biomed Pharmacother. 2017 Jun;90:821-834. doi: 10.1016/j.biopha.2017.04.025. Epub 2017 Apr 20. PubMed PMID: 28437886. 6: Ahmed AH, Gordon RD, Ward G, Wolley M, McWhinney BC, Ungerer JP, Stowasser M. Effect of Moxonidine on the Aldosterone/Renin Ratio in Healthy Male Volunteers. J Clin Endocrinol Metab. 2017 Jun 1;102(6):2039-2043. doi: 10.1210/jc.2016-3821. PubMed PMID: 28324033. 7: Ostroumova OD, Zykova AA. [Renoprotecion With Metabolic Syndrome: the Possibility of Receptor Agonist Imidazoline Moxonidine]. Kardiologiia. 2016 Oct;56(10):72-79. Russian. PubMed PMID: 28290898. 8: Parkin ML, Lim K, Burke SL, Head GA. Comparison in Conscious Rabbits of the Baroreceptor-Heart Rate Reflex Effects of Chronic Treatment with Rilmenidine, Moxonidine, and Clonidine. Front Physiol. 2016 Nov 15;7:522. eCollection 2016. PubMed PMID: 27895591; PubMed Central PMCID: PMC5108798. 9: Filipic S, Elek M, Popović M, Nikolic K, Agbaba D. Development of Hydrophilic Interaction Liquid Chromatography Method for the Analysis of Moxonidine and Its Impurities. J Anal Methods Chem. 2016;2016:3715972. Epub 2016 Oct 26. PubMed PMID: 27847672; PubMed Central PMCID: PMC5101389. 10: Cobos-Puc LE, Sánchez-López A, Centurión D. Pharmacological analysis of the cardiac sympatho-inhibitory actions of moxonidine and agmatine in pithed spontaneously hypertensive rats. Eur J Pharmacol. 2016 Nov 15;791:25-36. doi: 10.1016/j.ejphar.2016.08.017. Epub 2016 Aug 24. PubMed PMID: 27565220. 11: Kumar S, Kansal M, Kumar S, Goyal A. Comparative evaluation of therapeutic effect of Moxonidine versus Amlodipine on blood pressure in obese hypertensives. J Assoc Physicians India. 2016 Jan;64(1):54. PubMed PMID: 27727749. 12: El-Sayed SS, Zakaria MN, Abdel-Ghany RH, Abdel-Rahman AA. Cystathionine-γ lyase-derived hydrogen sulfide mediates the cardiovascular protective effects of moxonidine in diabetic rats. Eur J Pharmacol. 2016 Jul 15;783:73-84. doi: 10.1016/j.ejphar.2016.04.054. Epub 2016 Apr 29. PubMed PMID: 27138707; PubMed Central PMCID: PMC4893977. 13: Cobos-Puc LE, Aguayo-Morales H, Silva-Belmares Y, González-Zavala MA, Centurión D. α2A-adrenoceptors, but not nitric oxide, mediate the peripheral cardiac sympatho-inhibition of moxonidine. Eur J Pharmacol. 2016 Jul 5;782:35-43. doi: 10.1016/j.ejphar.2016.04.043. Epub 2016 Apr 22. PubMed PMID: 27112661. 14: Wang YK, Yu Q, Tan X, Wu ZT, Zhang RW, Yang YH, Yuan WJ, Hu QK, Wang WZ. Centrally acting drug moxonidine decreases reactive oxygen species via inactivation of the phosphoinositide-3 kinase signaling in the rostral ventrolateral medulla in hypertensive rats. J Hypertens. 2016 May;34(5):993-1004. doi: 10.1097/HJH.0000000000000887. PubMed PMID: 26886567. 15: Alves TB, Totola LT, Takakura AC, Colombari E, Moreira TS. GABA mechanisms of the nucleus of the solitary tract regulates the cardiovascular and sympathetic effects of moxonidine. Auton Neurosci. 2016 Jan;194:1-7. doi: 10.1016/j.autneu.2015.11.001. Epub 2015 Nov 14. PubMed PMID: 26633249. 16: Seyit M, Erdur B, Kortunay S, Yuksel A, Yilmaz A, Ozen M, Uyanik A, Tomruk O, Ergin A. A Comparison of Dexmedetomidine, Moxonidine and Alpha-Methyldopa Effects on Acute, Lethal Cocaine Toxicity. Iran Red Crescent Med J. 2015 Jun 1;17(6):e18780. doi: 10.5812/ircmj.17(5)2015.18780. eCollection 2015 Jun. PubMed PMID: 26290748; PubMed Central PMCID: PMC4537789. 17: Talih F, Ghossoub E. Moxonidine for tramadol withdrawal symptoms during detoxification. BMJ Case Rep. 2015 Jul 8;2015. pii: bcr2015210444. doi: 10.1136/bcr-2015-210444. PubMed PMID: 26156837; PubMed Central PMCID: PMC4499750. 18: Sarac B, Korkmaz O, Altun A, Bagcivan I, Göksel S, Yildirim S, Berkan O. Investigation of the vasorelaxant effects of moxonidine and its relaxation mechanism on the human radial artery when used as a coronary bypass graft. Interact Cardiovasc Thorac Surg. 2015 Sep;21(3):342-5. doi: 10.1093/icvts/ivv136. Epub 2015 May 25. PubMed PMID: 26015507. 19: Ilik MK, Kocaogullar Y, Koc O, Esen H. Beneficial effects of moxonidine on cerebral vasospasm after experimental subarachnoid hemorrhage. Turk Neurosurg. 2014;24(6):873-9. doi: 10.5137/1019-5149.JTN.9371-13.5. PubMed PMID: 25448203. 20: Karlafti E, Hatzitolios A, Savopoulos Ch. The role of moxonidine, a second generation centrally acting antihypertensive agent as antihypertensive therapy in the obese. Hippokratia. 2014 Apr;18(2):189. PubMed PMID: 25336891; PubMed Central PMCID: PMC4201414.