Synonym
Cartazolate, NSC166873, NSC-166873,NSC 166873; SQ-65,396; SQ-65396; SQ 65396; SQ65396;
IUPAC/Chemical Name
1H-Pyrazolo(3,4-b)pyridine-5-carboxylic acid, 4-(butylamino)-1-ethyl-, ethyl ester
InChi Key
IQNQAOGGWGCROX-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H22N4O2/c1-4-7-8-16-13-11-10-18-19(5-2)14(11)17-9-12(13)15(20)21-6-3/h9-10H,4-8H2,1-3H3,(H,16,17)
SMILES Code
O=C(C1=CN=C(N(CC)N=C2)C2=C1NCCCC)OCC
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
290.37
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 |
1: Kripalani KJ, Dreyfuss J, Nemec J, Cohen AI, Meeker F, Egli P. Biotransformation in the monkey of cartazolate (SQ 65,396), a substituted pyrazolopyridine having anxiolytic activity. Xenobiotica. 1981 Jul;11(7):481-8. doi: 10.3109/00498258109045858. PMID: 6117154.
2: Sathananthan G, Mir P, Minn FL, Gershon S. Antidepressant predictability: cartazolate. Curr Ther Res Clin Exp. 1976 Apr;19(4):475-8. PMID: 816605.
3: 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.
4: Hammond JR, Martin IL. Modulation of [3H]flunitrazepam binding to rat cerebellar benzodiazepine receptors by phosphatidylserine. Eur J Pharmacol. 1987 May 7;137(1):49-58. doi: 10.1016/0014-2999(87)90181-6. PMID: 3038577.
5: Supavilai P, Karobath M. Action of pyrazolopyridines as modulators of [3H]flunitrazepam binding to the gaba/benzodiazepine receptor complex of the cerebellum. Eur J Pharmacol. 1981 Mar 12;70(2):183-93. doi: 10.1016/0014-2999(81)90213-2. PMID: 6114867.
6: Hammond JR, Martin IL. Solubilization of the benzodiazepine/gamma- aminobutyric acid receptor complex: comparison of the detergents octylglucopyranoside and 3-[(3-cholamidopropyl)-dimethylammonio]1-propanesulfonate (CHAPS). J Neurochem. 1986 Oct;47(4):1161-71. doi: 10.1111/j.1471-4159.1986.tb00735.x. PMID: 3018163.
7: Koenig JA, Martin IL. Effect of free fatty acids on GABAA receptor ligand binding. Biochem Pharmacol. 1992 Jul 7;44(1):11-5. doi: 10.1016/0006-2952(92)90031-d. PMID: 1321625.
8: Niehoff DL, Mashal RD, Horst WD, O'Brien RA, Palacios JM, Kuhar MJ. Binding of a radiolabeled triazolopyridazine to a subtype of benzodiazepine receptor in the rat cerebellum. J Pharmacol Exp Ther. 1982 Jun;221(3):670-5. PMID: 6283058.
9: Wachtel H. Characteristic behavioural alterations in rats induced by rolipram and other selective adenosine cyclic 3', 5'-monophosphate phosphodiesterase inhibitors. Psychopharmacology (Berl). 1982;77(4):309-16. doi: 10.1007/BF00432761. PMID: 6182575.
10: Williams M. Anxioselective anxiolytics. J Med Chem. 1983 May;26(5):619-28. doi: 10.1021/jm00359a001. PMID: 6132997.
