Guanabenz acetate | CAS#23256-50-0 | α2A-AR agonist | IGRS Selective Ligand

MedKoo Cat#: 317126 | Name: Guanabenz acetate

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Description:

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

Guanabenz acetate is an α2A-AR adrenergic agonist and IGRS (imidazoline I2 binding site) selective ligand. Guanabenz acetate is an activator of alpha2B-AR (α2b-adrenergic receptor) and alpha2C-AR (α2c-adrenergic receptor). It is also used as an antihypertensive drug to treat high blood pressure.

Chemical Structure

Guanabenz acetate

CAS#23256-50-0 (acetate)

Theoretical Analysis

MedKoo Cat#: 317126

Name: Guanabenz acetate

CAS#: 23256-50-0 (acetate)

Chemical Formula: C10H12Cl2N4O2

Exact Mass: 0.0000

Molecular Weight: 291.13

Elemental Analysis: C, 41.26; H, 4.15; Cl, 24.35; N, 19.24; O, 10.99

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 650.00	2 Weeks

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Related CAS #

23256-50-0 (acetate) 5051-62-7 (free base) 23113-43-1 (HCl)

Synonym

Guanabenz acetate; Guanabenz monoacetate; Wytensin; WY-8678; WY 8678; WY8678; NSC-757044; NSC757044; NSC 757044

IUPAC/Chemical Name

[(2,6-Dichlorobenzylidene)amino]guanidine acetate

InChi Key

MCSPBPXATWBACD-GAYQJXMFSA-N

InChi Code

InChI=1S/C8H8Cl2N4.C2H4O2/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12;1-2(3)4/h1-4H,(H4,11,12,14);1H3,(H,3,4)/b13-4+;

SMILES Code

NC(N/N=C/C1=C(Cl)C=CC=C1Cl)=N.CC(O)=O

Appearance

White to off-white solid powder.

Purity

>96% (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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Guanabenz (Acetate) (BR-750) is an alpha-2 selective adrenergic agonist used as an antihypertensive agent.

In vitro activity:

Lipopolysaccharide (LPS)-stimulated RAW264.7 cells and mouse primary macrophages elevated the mRNA levels of IL1β, IL6, TNFα, and Cox2, but their elevation was significantly reduced by administration of 10 µM guanabenz for 6 h (Figure 1A,B). The mRNA levels of IL2 and IFNγ were increased in phorbol myristate acetate (PMA)-stimulated Jurkat cells, while those of TNFα and IL13 were upregulated in PMA-stimulated HMC1.1 cells. However, administration of 5 or 10 µM guanabenz significantly suppressed the upregulated mRNA levels (Figure 1C,D). Reference: Int J Mol Sci. 2016 May 5;17(5):674. https://pubmed.ncbi.nlm.nih.gov/27164082/

In vivo activity:

Administration of guanabenz for 12 weeks decreased the numbers of IL-1β positive cells in both WKY rats and SHRs (Fig. 7D and E). The numbers of IL-6 positive cells and its score decreased in SHRs treated with guanabenz for 8 weeks compared with SHRs (Fig. 8A and B). Guanabenz decreased the numbers of IL-6 positive cells and score of IL-6 in both WKY rats and SHRs (Fig. 8D, E and F). Reference: J Pharmacol Sci. 2021 Nov;147(3):294-304. https://pubmed.ncbi.nlm.nih.gov/34507638/

	Solvent	mg/mL	mM
Solubility
	DMSO	43.6	149.81
	Ethanol	5.0	17.17

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 291.13 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. Perego J, Bourbon C, Chasson L, Laprie C, Spinelli L, Camosseto V, Gatti E, Pierre P. Guanabenz Prevents dGalactosamine/Lipopolysaccharide-Induced Liver Damage and Mortality. Front Immunol. 2017 Jun 13;8:679. doi: 10.3389/fimmu.2017.00679. PMID: 28659918; PMCID: PMC5468566. 2. Takigawa S, Chen A, Nishimura A, Liu S, Li BY, Sudo A, Yokota H, Hamamura K. Guanabenz Downregulates Inflammatory Responses via eIF2α Dependent and Independent Signaling. Int J Mol Sci. 2016 May 5;17(5):674. doi: 10.3390/ijms17050674. PMID: 27164082; PMCID: PMC4881500. 3. Witkamp D, Oudejans E, Hu-A-Ng GV, Hoogterp L, Krzywańska AM, Žnidaršič M, Marinus K, de Veij Mestdagh CF, Bartelink I, Bugiani M, van der Knaap MS, Abbink TEM. Guanabenz ameliorates disease in vanishing white matter mice in contrast to sephin1. Ann Clin Transl Neurol. 2022 Aug;9(8):1147-1162. doi: 10.1002/acn3.51611. Epub 2022 Jul 1. PMID: 35778832; PMCID: PMC9380178. 4. Muramatsu R, Sato T, Hamamura K, Miyazawa K, Takeguchi A, Tabuchi M, Togari A, Goto S. Guanabenz inhibits alveolar bone resorption in a rat model of periodontitis. J Pharmacol Sci. 2021 Nov;147(3):294-304. doi: 10.1016/j.jphs.2021.08.003. Epub 2021 Aug 14. PMID: 34507638.

In vitro protocol:

In vivo protocol:

1. Witkamp D, Oudejans E, Hu-A-Ng GV, Hoogterp L, Krzywańska AM, Žnidaršič M, Marinus K, de Veij Mestdagh CF, Bartelink I, Bugiani M, van der Knaap MS, Abbink TEM. Guanabenz ameliorates disease in vanishing white matter mice in contrast to sephin1. Ann Clin Transl Neurol. 2022 Aug;9(8):1147-1162. doi: 10.1002/acn3.51611. Epub 2022 Jul 1. PMID: 35778832; PMCID: PMC9380178. 2. Muramatsu R, Sato T, Hamamura K, Miyazawa K, Takeguchi A, Tabuchi M, Togari A, Goto S. Guanabenz inhibits alveolar bone resorption in a rat model of periodontitis. J Pharmacol Sci. 2021 Nov;147(3):294-304. doi: 10.1016/j.jphs.2021.08.003. Epub 2021 Aug 14. PMID: 34507638.

1: Igaki N, Yamada H, Oimomi M, Kasuga M. The effective inhibition of the Maillard reaction by guanabenz acetate, and its relevance to the prevention of diabetic complications. Clin Chim Acta. 1991 May 31;199(1):113-5. PubMed PMID: 1934497. 2: Kotake H, Kinugawa T, Hirai S, Matsumoto T, Fukuki M, Hasegawa J, Mashiba H. Effects of guanabenz acetate on the pacemaker activity of rabbit sinoatrial node cells. Arch Int Pharmacodyn Ther. 1989 Jul-Aug;300:209-17. PubMed PMID: 2619423. 3: Spritzer N, Spritzer TS, Rodrigues R. [Guanabenz acetate and serum lipids. Sequential evaluation during one year]. Arq Bras Cardiol. 1988 Aug;51(2):193-7. Portuguese. PubMed PMID: 3075114. 4: LaRusso P, Jessup SA, Rogers FJ, Rogers JC. Sinoatrial and atrioventricular dysfunction associated with the use of guanabenz acetate. Can J Cardiol. 1988 Apr;4(3):146-8. PubMed PMID: 3378199. 5: Harvengt C. Drugs recently released in Belgium. Guanabenz acetate, isotretinoin and etretinate. Acta Clin Belg. 1986;41(1):60-3. PubMed PMID: 3458348. 6: Tennant FS Jr, Rawson RA. Guanabenz acetate: a new, long-acting alpha-two adrenergic agonist for opioid withdrawal. NIDA Res Monogr. 1984 Mar;49:338-43. PubMed PMID: 6090917. 7: Capuzzi DM, Cevallos WH. Inhibition of hepatic cholesterol and triglyceride synthesis by guanabenz acetate. J Cardiovasc Pharmacol. 1984;6 Suppl 5:S847-52. PubMed PMID: 6084138. 8: Grenfell RF. Double-blind study of guanabenz acetate in hypertensive patients. South Med J. 1983 Feb;76(2):199-201. PubMed PMID: 6337405.