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MedKoo Cat#: 532700 | Name: SIB-1757
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Description:

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

SIB-1757 is a highly selective antagonist for the mGlu5 metabotropic glutamate receptor subtype. SIB-1757 displays an IC50 value of 0.4 μM at hmGlu5 compared with > 30 μM at hmGlu1b, hmGlu2, hmGlu4, hmGlu6, hmGlu7 and hmGlu8.

Chemical Structure

SIB-1757
SIB-1757
CAS#31993-01-8

Theoretical Analysis

MedKoo Cat#: 532700

Name: SIB-1757

CAS#: 31993-01-8

Chemical Formula: C12H11N3O

Exact Mass: 213.0902

Molecular Weight: 213.24

Elemental Analysis: C, 67.59; H, 5.20; N, 19.71; O, 7.50

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 450.00 2 Weeks
25mg USD 550.00 2 Weeks
50mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
SIB-1757; SIB 1757; SIB1757.
IUPAC/Chemical Name
6-Methyl-2-(phenylazo)-3-pyridinol
InChi Key
LOCPVWIREQIGNQ-CCEZHUSRSA-N
InChi Code
InChI=1S/C12H11N3O/c1-9-7-8-11(16)12(13-9)15-14-10-5-3-2-4-6-10/h2-8,16H,1H3/b15-14+
SMILES Code
OC1=CC=C(C)N=C1/N=N/C2=CC=CC=C2
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, DMF, and ethanol
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:
SIB-1757 is a highly selective and noncompetitive antagonist of mGlu5 receptor with an IC50 of 0.4 μM. It selectively inhibits glutamate-induced calcium release and quisqualate-induced phosphoinositol accumulation in fibroblasts expressing human mGluR5a (IC50s = 0.37 and 3.1 µM, respectively) over mGluR1b-expressing fibroblasts (IC50s = >100 µM for both). SIB 1757 is also selective for mGluR5a over mGluR2, mGluR3, mGluR4a, mGluR6, mGluR7b, mGluR8 (IC50s = >100 µM for all), as well as AMPA, kainate, and NMDA receptors (IC50s = >30 µM for all). It inhibits phosphoinositol accumulation induced by the group I mGluR agonist (S)-3,5-DHPG in isolated neonatal rat hippocampus and striatum (IC50s = 5.2 and 10.1 µM, respectively).
In vitro activity:
SIB 1757 was used to inhibit mGluR5, preventing the membrane depolarization/inward current induced by 3,5-DHPG. This blockade of mGluR5 was observed to prevent receptor desensitization, contrasting with the effects seen with LY 367385. The study suggests that mGluR5 (modulated by SIB 1757) plays a role in shaping the activity of mGluR1 and influencing cell excitability in striatal cholinergic interneurons. Reference: Neuropharmacology. 2005;49 Suppl 1:104-13. https://pubmed.ncbi.nlm.nih.gov/16005029/
In vivo activity:
Pharmacological blockade of mGlu5 receptors might represent a novel target for the treatment of drug-induced liver damage. In mice, a single injection of acetaminophen (300 mg/kg, i.p.) induced centrilobular liver necrosis, which was detectable after 24 h. However, SIB-1757 (at 20 mg/kg, i.p.) reduced the increased expression and activity of liver iNOS induced by acetaminophen. Reference: J Hepatol. 2003 Feb;38(2):179-87. https://pubmed.ncbi.nlm.nih.gov/12547406/
Solvent mg/mL mM comments
Solubility
DMF 14.0 65.65
DMSO 14.0 65.65
Ethanol 5.0 23.45
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 213.24 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. Bonsi P, Cuomo D, De Persis C, Centonze D, Bernardi G, Calabresi P, Pisani A. Modulatory action of metabotropic glutamate receptor (mGluR) 5 on mGluR1 function in striatal cholinergic interneurons. Neuropharmacology. 2005;49 Suppl 1:104-13. doi: 10.1016/j.neuropharm.2005.05.012. PMID: 16005029. 2. Varney MA, Cosford ND, Jachec C, Rao SP, Sacaan A, Lin FF, Bleicher L, Santori EM, Flor PJ, Allgeier H, Gasparini F, Kuhn R, Hess SD, Veliçelebi G, Johnson EC. SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5. J Pharmacol Exp Ther. 1999 Jul;290(1):170-81. PMID: 10381773. 3. Storto M, Ngomba RT, Battaglia G, Freitas I, Griffini P, Richelmi P, Nicoletti F, Vairetti M. Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice. J Hepatol. 2003 Feb;38(2):179-87. doi: 10.1016/s0168-8278(02)00384-7. PMID: 12547406. 4. Dogrul A, Ossipov MH, Lai J, Malan TP Jr, Porreca F. Peripheral and spinal antihyperalgesic activity of SIB-1757, a metabotropic glutamate receptor (mGLUR(5)) antagonist, in experimental neuropathic pain in rats. Neurosci Lett. 2000 Oct 6;292(2):115-8. doi: 10.1016/s0304-3940(00)01458-0. PMID: 10998562.
In vitro protocol:
1. Bonsi P, Cuomo D, De Persis C, Centonze D, Bernardi G, Calabresi P, Pisani A. Modulatory action of metabotropic glutamate receptor (mGluR) 5 on mGluR1 function in striatal cholinergic interneurons. Neuropharmacology. 2005;49 Suppl 1:104-13. doi: 10.1016/j.neuropharm.2005.05.012. PMID: 16005029. 2. Varney MA, Cosford ND, Jachec C, Rao SP, Sacaan A, Lin FF, Bleicher L, Santori EM, Flor PJ, Allgeier H, Gasparini F, Kuhn R, Hess SD, Veliçelebi G, Johnson EC. SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5. J Pharmacol Exp Ther. 1999 Jul;290(1):170-81. PMID: 10381773.
In vivo protocol:
1. Storto M, Ngomba RT, Battaglia G, Freitas I, Griffini P, Richelmi P, Nicoletti F, Vairetti M. Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice. J Hepatol. 2003 Feb;38(2):179-87. doi: 10.1016/s0168-8278(02)00384-7. PMID: 12547406. 2. Dogrul A, Ossipov MH, Lai J, Malan TP Jr, Porreca F. Peripheral and spinal antihyperalgesic activity of SIB-1757, a metabotropic glutamate receptor (mGLUR(5)) antagonist, in experimental neuropathic pain in rats. Neurosci Lett. 2000 Oct 6;292(2):115-8. doi: 10.1016/s0304-3940(00)01458-0. PMID: 10998562.
1. Varney et al (1999) SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5. J.Pharmacol.Exp.Ther. 290 170. PMID: 10381773.