Synonym
Guanabenz; Guanabenzo; Guanabenzum; WY-8678; WY 8678; WY8678; NSC-68982; NSC68982; NSC 68982;
IUPAC/Chemical Name
2-[(E)-(2,6-dichlorophenyl)methylideneamino]guanidine
InChi Key
WDZVGELJXXEGPV-YIXHJXPBSA-N
InChi Code
InChI=1S/C8H8Cl2N4/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12/h1-4H,(H4,11,12,14)/b13-4+
SMILES Code
N/C(N)=N\N=C\C1=C(Cl)C=CC=C1Cl
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
Biological target:
Guanabenz is an orally active α-2-adrenoceptor agonist.
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 |
12.0 |
51.93 |
| Ethanol |
15.0 |
64.91 |
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
231.08
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 d-Galactosamine/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:
1. Perego J, Bourbon C, Chasson L, Laprie C, Spinelli L, Camosseto V, Gatti E, Pierre P. Guanabenz Prevents d-Galactosamine/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.
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.
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