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MedKoo Cat#: 524445 | Name: BMS-191011
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Description:

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

BMS 191011 is a potent KCa1.1 (BK) channel opener. It is also neuroprotectant in two distinct animal models of stroke- MCAO in the SHR rat and a normotensive model of focal stroke.

Chemical Structure

BMS-191011
BMS-191011
CAS#202821-81-6

Theoretical Analysis

MedKoo Cat#: 524445

Name: BMS-191011

CAS#: 202821-81-6

Chemical Formula: C16H10ClF3N2O3

Exact Mass: 370.0332

Molecular Weight: 370.71

Elemental Analysis: C, 51.84; H, 2.72; Cl, 9.56; F, 15.37; N, 7.56; O, 12.95

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 2,150.00 Ready to ship
1g USD 2,950.00 Ready to ship
2g USD 5,150.00 Ready to ship
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Synonym
BMS-191011; BMS 191011; BMS191011; UNII-LW7MXS978N; Bms-a.
IUPAC/Chemical Name
1,3,4-Oxadiazol-2(3H)-one, 3-((5-chloro-2-hydroxyphenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-
InChi Key
QKOWACXSXTXRKA-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H10ClF3N2O3/c17-12-5-6-13(23)10(7-12)8-22-15(24)25-14(21-22)9-1-3-11(4-2-9)16(18,19)20/h1-7,23H,8H2
SMILES Code
c1cc(ccc1c2nn(c(=O)o2)Cc3cc(ccc3O)Cl)C(F)(F)F
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, not in water
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
Biological target:
BMS-191011 (BMS-A) is an opener of the large-conductance, Ca2+-activated potassium (maxi-K) channel, effective in stroke models.
In vitro activity:
In vivo activity:
The effects of BMS-191011 was examined openers of BK(Ca) channels, on rat retinal blood vessels in vivo. Male Wistar rats (8- to 10-week-old) were anesthetized with pentobarbital sodium (50 mg/kg, intraperitoneally (i.p.)) and treated with tetrodotoxin (50 µg/kg, intravenously (i.v.)) to eliminate any nerve activity and prevent movement of the eye under artificial ventilation. A mixture solution of adrenaline and noradrenaline (9:1) was infused to maintain adequate systemic circulation. BMS-191011 (10-100 µg/kg, i.v.) increased the diameter of retinal arterioles without altering systemic blood pressure and heart rate significantly. The vasodilator responses to BMS-191011 were significantly diminished by intravitreal injection of iberiotoxin (an inhibitor of BK(Ca) channels, 20 pmol/eye). These results suggest that BMS-191011 dilates rat retinal arterioles through activation of iberiotoxin-sensitive BK(Ca) channels in vivo. The BK(Ca) channel opener could be considered as a candidate for improving retinal circulation without severe cardiovascular side-effects. Reference: Biol Pharm Bull. 2011;34(1):150-2. http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/34.150?from=PubMed
Solvent mg/mL mM
Solubility
DMSO 20.0 54.00
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 370.71 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:
In vitro protocol:
In vivo protocol:
1. Mori A, Suzuki S, Sakamoto K, Nakahara T, Ishii K. BMS-191011, an opener of large-conductance Ca2+-activated potassium channels, dilates rat retinal arterioles in vivo. Biol Pharm Bull. 2011;34(1):150-2. doi: 10.1248/bpb.34.150. PMID: 21212534.
1: Levin SG, Konakov MV, Godukhin OV. Role of BKCa Potassium Channels in the Mechanisms of Modulatory Effects of IL-10 on Hypoxia-Induced Changes in Activity of Hippocampal Neurons. Bull Exp Biol Med. 2016 Mar;160(5):643-5. doi: 10.1007/s10517-016-3238-0. Epub 2016 Mar 29. PubMed PMID: 27021102. 2: Ji F, Li X, Guo W, Wu W, Jiang H. Palladium-Catalyzed Oxidative O-H/N-H Carbonylation of Hydrazides: Access to Substituted 1,3,4-Oxadiazole-2(3H)-ones. J Org Chem. 2015 Jun 5;80(11):5713-8. doi: 10.1021/acs.joc.5b00664. Epub 2015 May 20. PubMed PMID: 25973639. 3: Mori A, Takei T, Sakamoto K, Nakahara T, Ishii K. 4-Hydroxy-2-nonenal attenuates β2-adrenoceptor-mediated vasodilation of rat retinal arterioles. Naunyn Schmiedebergs Arch Pharmacol. 2015 May;388(5):575-82. doi: 10.1007/s00210-015-1099-0. Epub 2015 Feb 19. PubMed PMID: 25693977. 4: Shukla P, Ghatta S, Dubey N, Lemley CO, Johnson ML, Modgil A, Vonnahme K, Caton JS, Reynolds LP, Sun C, O'Rourke ST. Maternal nutrient restriction during pregnancy impairs an endothelium-derived hyperpolarizing factor-like pathway in sheep fetal coronary arteries. Am J Physiol Heart Circ Physiol. 2014 Jul 15;307(2):H134-42. doi: 10.1152/ajpheart.00595.2013. Epub 2014 May 9. PubMed PMID: 24816259; PubMed Central PMCID: PMC4101639. 5: Mori A, Suzuki S, Sakamoto K, Nakahara T, Ishii K. Vasodilation of retinal arterioles induced by activation of BKCa channels is attenuated in diabetic rats. Eur J Pharmacol. 2011 Nov 1;669(1-3):94-9. doi: 10.1016/j.ejphar.2011.07.042. Epub 2011 Aug 19. PubMed PMID: 21871885. 6: Mori A, Suzuki S, Sakamoto K, Nakahara T, Ishii K. BMS-191011, an opener of large-conductance Ca2+-activated potassium channels, dilates rat retinal arterioles in vivo. Biol Pharm Bull. 2011;34(1):150-2. PubMed PMID: 21212534. 7: Mori A, Suzuki S, Sakamoto K, Nakahara T, Ishii K. Role of calcium-activated potassium channels in acetylcholine-induced vasodilation of rat retinal arterioles in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2011 Jan;383(1):27-34. doi: 10.1007/s00210-010-0570-1. Epub 2010 Oct 27. PubMed PMID: 20978884. 8: Romine JL, Martin SW, Meanwell NA, Gribkoff VK, Boissard CG, Dworetzky SI, Natale J, Moon S, Ortiz A, Yeleswaram S, Pajor L, Gao Q, Starrett JE Jr. 3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl ]-1,3,4-oxadiazol-2(3H)-one, BMS-191011: opener of large-conductance Ca(2+)-activated potassium (maxi-K) channels, identification, solubility, and SAR. J Med Chem. 2007 Feb 8;50(3):528-42. PubMed PMID: 17266205. 9: Hewawasam P, Ding M, Chen N, King D, Knipe J, Pajor L, Ortiz A, Gribkoff VK, Starrett J. Synthesis of water-soluble prodrugs of BMS-191011: a maxi-K channel opener targeted for post-stroke neuroprotection. Bioorg Med Chem Lett. 2003 May 19;13(10):1695-8. PubMed PMID: 12729644.