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MedKoo Cat#: 574688 | Name: Etazolate hydrochloride
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Description:

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

Etazolate hydrochloride is a PDE4 inhibitor.

Chemical Structure

Etazolate hydrochloride
Etazolate hydrochloride
CAS#35838-58-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 574688

Name: Etazolate hydrochloride

CAS#: 35838-58-5 (HCl)

Chemical Formula: C14H20ClN5O2

Exact Mass: 325.1306

Molecular Weight: 325.80

Elemental Analysis: C, 51.61; H, 6.19; Cl, 10.88; N, 21.50; O, 9.82

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
10mg USD 450.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
51022-77-6 (free base) 35838-58-5 (HCl)
Synonym
Etazolate hydrochloride; Etazolate HCl; SQ64442; SQ 64442; SQ-64442; NSC163611; NSC 163611; NSC-163611;
IUPAC/Chemical Name
1-Ethyl-4-[(1-methylethylidene)hydrazino]-1H-pyrazolo-[3,4-b]-pyridine-5-carboxylic acid, ethyl ester hydrochloride
InChi Key
GQJUGJHJUZSJLZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H19N5O2.ClH/c1-5-19-13-10(8-16-19)12(18-17-9(3)4)11(7-15-13)14(20)21-6-2;/h7-8H,5-6H2,1-4H3,(H,15,18);1H
SMILES Code
O=C(C1=CN=C(N(CC)N=C2)C2=C1N/N=C(C)\C)OCC.[H]Cl
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
>3 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:
Etazolate hydrochloride is a PDE4 inhibitor.
In vitro activity:
Induction of secreted sAPPα was dose-dependent and Fig. 1(a) shows a representative gel depicting an increase in sAPPα secretion with increasing concentrations of etazolate after a 24h treatment. sAPPα induction occurred as early as 4h (data not shown). The levels of secreted sAPPα after treatment with nanomolar and micromolar concentrations of etazolate reached a plateau, and maximal sAPPα level was obtained at 2 μM etazolate and was about 2.9-fold above its basal level (Fig. 1b). At concentrations as low as 0.2 μM, etazolate generated a two fold induction over basal level. At higher concentrations (i.e. 10 μM), no further increase was evidenced (data not shown). Reference: J Neurochem. 2008 Jul;106(1):392-404. https://pubmed.ncbi.nlm.nih.gov/18397369/
In vivo activity:
Results revealed that PTSD potentiated oxidative stress in the hippocampus and induced significant reductions in BDNF level and histones acetylation (P < 0.05). Etazolate treatment, on the other hand, led to prevention of changes in these oxidative stress biomarkers (GSH, GSSG, GPx and TBARS), BDNF levels, and histones acetylation. In conclusion, oxidative stress and modulation of BDNF and histones acetylation induced by PTSD can be prevented by treatment with etazolate. Reference: Behav Brain Res. 2019 Sep 2;369:111930. https://pubmed.ncbi.nlm.nih.gov/31047921/

Preparing Stock Solutions

The following data is based on the product molecular weight 325.80 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
Formulation protocol:
1. Marcade M, Bourdin J, Loiseau N, Peillon H, Rayer A, Drouin D, Schweighoffer F, Désiré L. Etazolate, a neuroprotective drug linking GABA(A) receptor pharmacology to amyloid precursor protein processing. J Neurochem. 2008 Jul;106(1):392-404. doi: 10.1111/j.1471-4159.2008.05396.x. Epub 2008 Jul 1. PMID: 18397369. 2. Alzoubi KH, Al Subeh ZY, Khabour OF. Molecular targets for the interactive effect of etazolate during post-traumatic stress disorder: Role of oxidative stress, BDNF and histones. Behav Brain Res. 2019 Sep 2;369:111930. doi: 10.1016/j.bbr.2019.111930. Epub 2019 May 6. PMID: 31047921. 3. Alzoubi KH, Mokhemer E, Abuirmeileh AN. Beneficial effect of etazolate on depression-like behavior and, learning, and memory impairment in a model of Parkinson's disease. Behav Brain Res. 2018 Sep 17;350:109-115. doi: 10.1016/j.bbr.2018.05.004. Epub 2018 May 11. PMID: 29758248.
In vitro protocol:
1. Marcade M, Bourdin J, Loiseau N, Peillon H, Rayer A, Drouin D, Schweighoffer F, Désiré L. Etazolate, a neuroprotective drug linking GABA(A) receptor pharmacology to amyloid precursor protein processing. J Neurochem. 2008 Jul;106(1):392-404. doi: 10.1111/j.1471-4159.2008.05396.x. Epub 2008 Jul 1. PMID: 18397369.
In vivo protocol:
1. Alzoubi KH, Al Subeh ZY, Khabour OF. Molecular targets for the interactive effect of etazolate during post-traumatic stress disorder: Role of oxidative stress, BDNF and histones. Behav Brain Res. 2019 Sep 2;369:111930. doi: 10.1016/j.bbr.2019.111930. Epub 2019 May 6. PMID: 31047921. 2. Alzoubi KH, Mokhemer E, Abuirmeileh AN. Beneficial effect of etazolate on depression-like behavior and, learning, and memory impairment in a model of Parkinson's disease. Behav Brain Res. 2018 Sep 17;350:109-115. doi: 10.1016/j.bbr.2018.05.004. Epub 2018 May 11. PMID: 29758248.
1: Carrete A, Padilla-Ferrer A, Simon A, Meffre D, Jafarian-Tehrani M. Effect of Etazolate upon Cuprizone-induced Demyelination In Vivo: Behavioral and Myelin Gene Analysis. Neuroscience. 2021 Feb 10;455:240-250. doi: 10.1016/j.neuroscience.2020.11.027. Epub 2020 Nov 24. PMID: 33246058. 2: Barnes DM, White WF, Dichter MA. Etazolate (SQ20009): electrophysiology and effects on [3H]flunitrazepam binding in cultured cortical neurons. J Neurosci. 1983 Apr;3(4):762-72. doi: 10.1523/JNEUROSCI.03-04-00762.1983. PMID: 6131949; PMCID: PMC6564462. 3: Jindal A, Mahesh R, Bhatt S. Etazolate, a phosphodiesterase 4 inhibitor reverses chronic unpredictable mild stress-induced depression-like behavior and brain oxidative damage. Pharmacol Biochem Behav. 2013 Apr;105:63-70. doi: 10.1016/j.pbb.2013.01.020. Epub 2013 Feb 4. PMID: 23384434. 4: Jindal A, Mahesh R, Bhatt S. Etazolate rescues behavioral deficits in chronic unpredictable mild stress model: modulation of hypothalamic-pituitary-adrenal axis activity and brain-derived neurotrophic factor level. Neurochem Int. 2013 Nov;63(5):465-75. doi: 10.1016/j.neuint.2013.08.005. Epub 2013 Aug 22. PMID: 23974048. 5: Guo J, Lin P, Zhao X, Zhang J, Wei X, Wang Q, Wang C. Etazolate abrogates the lipopolysaccharide (LPS)-induced downregulation of the cAMP/pCREB/BDNF signaling, neuroinflammatory response and depressive-like behavior in mice. Neuroscience. 2014 Mar 28;263:1-14. doi: 10.1016/j.neuroscience.2014.01.008. Epub 2014 Jan 13. PMID: 24434771. 6: Jindal A, Mahesh R, Bhatt S. Etazolate, a phosphodiesterase-4 enzyme inhibitor produces antidepressant-like effects by blocking the behavioral, biochemical, neurobiological deficits and histological abnormalities in hippocampus region caused by olfactory bulbectomy. Psychopharmacology (Berl). 2015 Feb;232(3):623-37. doi: 10.1007/s00213-014-3705-0. Epub 2014 Aug 15. PMID: 25120105. 7: Drott J, Desire L, Drouin D, Pando M, Haun F. Etazolate improves performance in a foraging and homing task in aged rats. Eur J Pharmacol. 2010 May 25;634(1-3):95-100. doi: 10.1016/j.ejphar.2010.02.036. Epub 2010 Mar 17. PMID: 20223232. 8: Alzoubi KH, Mokhemer E, Abuirmeileh AN. Beneficial effect of etazolate on depression-like behavior and, learning, and memory impairment in a model of Parkinson's disease. Behav Brain Res. 2018 Sep 17;350:109-115. doi: 10.1016/j.bbr.2018.05.004. Epub 2018 May 11. PMID: 29758248. 9: Siopi E, Llufriu-Dabén G, Cho AH, Vidal-Lletjós S, Plotkine M, Marchand- Leroux C, Jafarian-Tehrani M. Etazolate, an α-secretase activator, reduces neuroinflammation and offers persistent neuroprotection following traumatic brain injury in mice. Neuropharmacology. 2013 Apr;67:183-92. doi: 10.1016/j.neuropharm.2012.11.009. Epub 2012 Nov 23. PMID: 23178198. 10: Marcade M, Bourdin J, Loiseau N, Peillon H, Rayer A, Drouin D, Schweighoffer F, Désiré L. Etazolate, a neuroprotective drug linking GABA(A) receptor pharmacology to amyloid precursor protein processing. J Neurochem. 2008 Jul;106(1):392-404. doi: 10.1111/j.1471-4159.2008.05396.x. Epub 2008 Jul 1. PMID: 18397369. 11: Alzoubi KH, Al Subeh ZY, Khabour OF. Evaluating the protective effect of etazolate on memory impairment, anxiety- and depression-like behaviors induced by post traumatic stress disorder. Brain Res Bull. 2017 Oct;135:185-192. doi: 10.1016/j.brainresbull.2017.10.012. Epub 2017 Nov 3. PMID: 29107895. 12: Jindal A, Mahesh R, Gautam B, Bhatt S, Pandey D. Antidepressant-like effect of etazolate, a cyclic nucleotide phosphodiesterase 4 inhibitor--an approach using rodent behavioral antidepressant tests battery. Eur J Pharmacol. 2012 Aug 15;689(1-3):125-31. doi: 10.1016/j.ejphar.2012.05.051. Epub 2012 Jun 12. PMID: 22698578. 13: Alzoubi KH, Al Subeh ZY, Khabour OF. Molecular targets for the interactive effect of etazolate during post-traumatic stress disorder: Role of oxidative stress, BDNF and histones. Behav Brain Res. 2019 Sep 2;369:111930. doi: 10.1016/j.bbr.2019.111930. Epub 2019 May 6. PMID: 31047921. 14: Ankur J, Mahesh R, Bhatt S. Anxiolytic-like effect of etazolate, a type 4 phosphodiesterase inhibitor in experimental models of anxiety. Indian J Exp Biol. 2013 Jun;51(6):444-9. PMID: 23926692. 15: Psychoyos S, Ford CJ, Phillips MA. Inhibition by etazolate (SQ 20009) and cartazolate (SQ 65396) of adenosine-stimulated [3H]cAMP formation in [2-3H]adenine-prelabeled vesicles prepared from guinea pig cerebral cortex. Biochem Pharmacol. 1982 Apr 1;31(7):1441-2. doi: 10.1016/0006-2952(82)90041-7. PMID: 6284176. 16: Llufriu-Dabén G, Carrete A, Chierto E, Mailleux J, Camand E, Simon A, Vanmierlo T, Rose C, Allinquant B, Hendriks JJA, Massaad C, Meffre D, Jafarian- Tehrani M. Targeting demyelination via α-secretases promoting sAPPα release to enhance remyelination in central nervous system. Neurobiol Dis. 2018 Jan;109(Pt A):11-24. doi: 10.1016/j.nbd.2017.09.008. Epub 2017 Sep 18. PMID: 28923597. 17: Wang C, Zhang J, Lu Y, Lin P, Pan T, Zhao X, Liu A, Wang Q, Zhou W, Zhang HT. Antidepressant-like effects of the phosphodiesterase-4 inhibitor etazolate and phosphodiesterase-5 inhibitor sildenafil via cyclic AMP or cyclic GMP signaling in mice. Metab Brain Dis. 2014 Sep;29(3):673-82. doi: 10.1007/s11011-014-9533-4. Epub 2014 Apr 5. PMID: 24705918. 18: Ticku MK, Davis WC. Molecular interactions of etazolate with benzodiazepine and picrotoxinin binding sites. J Neurochem. 1982 Apr;38(4):1180-2. doi: 10.1111/j.1471-4159.1982.tb05370.x. PMID: 6278085. 19: Jindal A, Mahesh R, Bhatt S, Pandey D. Molecular modifications by regulating cAMP signaling and oxidant-antioxidant defence mechanisms, produce antidepressant-like effect: A possible mechanism of etazolate aftermaths of impact accelerated traumatic brain injury in rat model. Neurochem Int. 2017 Dec;111:3-11. doi: 10.1016/j.neuint.2016.12.004. Epub 2016 Dec 14. PMID: 27988361. 20: Borea PA, Supavilai P, Karobath M. Differential modulation of etazolate or pentobarbital enhanced [3H] muscimol binding by benzodiazepine agonists and inverse agonists. Brain Res. 1983 Dec 5;280(2):383-6. doi: 10.1016/0006-8993(83)90072-0. PMID: 6140072.