Synonym
SB 205384; SB-205384; SB205384.
IUPAC/Chemical Name
but-2-yn-1-yl (R)-4-amino-7-hydroxy-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-b]pyridine-3-carboxylate
InChi Key
JDTZAGLGBRRCJT-SNVBAGLBSA-N
InChi Code
InChI=1S/C17H18N2O3S/c1-3-4-7-22-17(21)13-9(2)19-16-14(15(13)18)11-6-5-10(20)8-12(11)23-16/h10,20H,5-8H2,1-2H3,(H2,18,19)/t10-/m1/s1
SMILES Code
O=C(C1=C(C)N=C2C(C3=C(C[C@H](O)CC3)S2)=C1N)OCC#CC
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
330.40
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: Freitas J, Miller N, Mengeling BJ, Xia M, Huang R, Houck K, Rietjens IM, Furlow JD, Murk AJ. Identification of thyroid hormone receptor active compounds using a quantitative high-throughput screening platform. Curr Chem Genom Transl Med. 2014 Mar 7;8:36-46. doi: 10.2174/2213988501408010036. PubMed PMID: 24772387; PubMed Central PMCID: PMC3999704.
2: Heidelberg LS, Warren JW, Fisher JL. SB-205384 is a positive allosteric modulator of recombinant GABAA receptors containing rat α3, α5, or α6 subunit subtypes coexpressed with β3 and γ2 subunits. J Pharmacol Exp Ther. 2013 Oct;347(1):235-41. doi: 10.1124/jpet.113.207324. PubMed PMID: 23902941; PubMed Central PMCID: PMC3781410.
3: Chun SK, Jo YH. Loss of leptin receptors on hypothalamic POMC neurons alters synaptic inhibition. J Neurophysiol. 2010 Nov;104(5):2321-8. doi: 10.1152/jn.00371.2010. PubMed PMID: 20844117; PubMed Central PMCID: PMC2997019.
4: Miller BH, Schultz LE, Long BC, Pletcher MT. Quantitative trait locus analysis identifies Gabra3 as a regulator of behavioral despair in mice. Mamm Genome. 2010 Jun;21(5-6):247-57. doi: 10.1007/s00335-010-9266-6. PubMed PMID: 20512339; PubMed Central PMCID: PMC2890984.
5: Navarro JF, Burón E, Martín-López M. Effects of SB-205384, a positive modulator of alpha3-subunit-containing GABA-A receptors, on isolation-induced aggression in male mice. Psicothema. 2008 Feb;20(1):144-7. PubMed PMID: 18206077.
6: Ing T, Poulter MO. Diversity of GABA(A) receptor synaptic currents on individual pyramidal cortical neurons. Eur J Neurosci. 2007 Feb;25(3):723-34. PubMed PMID: 17313570.
7: Navarro JF, Burón E, Martín-López M. Anxiolytic-like activity of SB-205384 in the elevated plus-maze test in mice. Psicothema. 2006 Feb;18(1):100-4. PubMed PMID: 17296016.
8: Hutcheon B, Morley P, Poulter MO. Developmental change in GABAA receptor desensitization kinetics and its role in synapse function in rat cortical neurons. J Physiol. 2000 Jan 1;522 Pt 1:3-17. PubMed PMID: 10618148; PubMed Central PMCID: PMC2269740.
9: Meadows HJ, Kumar CS, Pritchett DB, Blackburn TP, Benham CD. SB-205384: a GABA(A) receptor modulator with novel mechanism of action that shows subunit selectivity. Br J Pharmacol. 1998 Mar;123(6):1253-9. PubMed PMID: 9559912; PubMed Central PMCID: PMC1565273.
10: Meadows HJ, Harries MH, Thompson M, Benham CD. Effect of SB-205384 on the decay of GABA-activated chloride currents in granule cells cultured from rat cerebellum. Br J Pharmacol. 1997 Aug;121(7):1334-8. PubMed PMID: 9257911; PubMed Central PMCID: PMC1564816.
