MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 145012 | Name: MIDD0301 free acid
Featured New

Description:

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

MIDD0301 is a GABAAR modulator that binds GABAA receptors on airway smooth muscle and immune cells. MIDD0301 interconverts between stable structures at neutral and acidic pH without changes in bioavailability. MIDD0301 can selectively target lung GABAAR without adverse motor, cardiovascular, or respiratory effects and inhaled dosing is effective in reducing bronchoconstriction in allergen and infectious lung inflammation.

Chemical Structure

MIDD0301 free acid
MIDD0301 free acid
CAS#2187489-08-1 (free acid)

Theoretical Analysis

MedKoo Cat#: 145012

Name: MIDD0301 free acid

CAS#: 2187489-08-1 (free acid)

Chemical Formula: C19H13BrFN3O2

Exact Mass: 413.0175

Molecular Weight: 414.23

Elemental Analysis: C, 55.09; H, 3.16; Br, 19.29; F, 4.59; N, 10.14; O, 7.72

Price and Availability

Size Price Availability Quantity
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
50mg USD 1,650.00 2 Weeks
100mg USD 2,650.00 2 Weeks
1g USD 6,450.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
2593569-36-7 (sodium) 2187489-08-1 (free acid)
Synonym
MIDD-0301; MIDD0301; MIDD 0301; GL-II-93; MIDD0301 free acid;
IUPAC/Chemical Name
(R)-8-bromo-6-(2-fluorophenyl)-4-methyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid
InChi Key
OSBXEAZWQGBYFU-SNVBAGLBSA-N
InChi Code
1S/C19H13BrFN3O2/c1-10-18-17(19(25)26)22-9-24(18)15-7-6-11(20)8-13(15)16(23-10)12-4-2-3-5-14(12)21/h2-10H,1H3,(H,25,26)/t10-/m1/s1
SMILES Code
C[C@H]1N=C(C2=C(F)C=CC=C2)C3=C(C=CC(Br)=C3)N4C=NC(C(O)=O)=C14
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 414.23 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
1: Roni MSR, Zahn NM, Mikulsky BN, Webb DA, Mian MY, Knutson DE, Guthrie ML, Cook JM, Stafford DC, Arnold LA. Identification and Quantification of MIDD0301 Metabolites. Curr Drug Metab. 2021;22(14):1114-1123. doi: 10.2174/1389200222666211202093841. PMID: 34856893; PMCID: PMC8760168. 2: Zahn NM, Mikulsky BN, Roni MSR, Yocum GT, Mian MY, Knutson DE, Cook JM, Emala CW, Stafford DC, Arnold LA. Nebulized MIDD0301 Reduces Airway Hyperresponsiveness in Moderate and Severe Murine Asthma Models. ACS Pharmacol Transl Sci. 2020 Dec 2;3(6):1381-1390. doi: 10.1021/acsptsci.0c00180. PMID: 33344908; PMCID: PMC7737320. 3: Roni MSR, Li G, Mikulsky BN, Knutson DE, Mian MY, Zahn NM, Cook JM, Stafford DC, Arnold LA. The Effects of pH on the Structure and Bioavailability of Imidazobenzodiazepine-3-Carboxylate MIDD0301. Mol Pharm. 2020 Apr 6;17(4):1182-1192. doi: 10.1021/acs.molpharmaceut.9b01210. Epub 2020 Feb 26. PMID: 32069056; PMCID: PMC7216793. 4: Zahn NM, Huber AT, Mikulsky BN, Stepanski ME, Kehoe AS, Li G, Schussman M, Rashid Roni MS, Kodali R, Cook JM, Stafford DC, Steeber DA, Arnold LA. MIDD0301 - A first-in-class anti-inflammatory asthma drug targets GABAA receptors without causing systemic immune suppression. Basic Clin Pharmacol Toxicol. 2019 Jul;125(1):75-84. doi: 10.1111/bcpt.13206. Epub 2019 Feb 21. Erratum in: Basic Clin Pharmacol Toxicol. 2020 May;126(5):464. PMID: 30694594; PMCID: PMC6565495. 5: Rashid Roni MS, Zahn NM, Yocum GT, Webb DA, Mian MY, Meyer MJ, Tylek AS, Cook JM, Emala CW, Stafford DC, Arnold LA. Comparative pharmacodynamic and pharmacokinetic study of MIDD0301 and its (S) enantiomer. Drug Dev Res. 2022 Jun;83(4):979-992. doi: 10.1002/ddr.21926. Epub 2022 Mar 4. PMID: 35246861; PMCID: PMC9246881. 6: Knutson DE, Roni R, Mian Y, Cook JM, Stafford DC, Arnold LA. Improved scale- up synthesis and purification of clinical asthma candidate MIDD0301. Org Process Res Dev. 2020 Aug 21;24(8):1467-1476. doi: 10.1021/acs.oprd.0c00200. Epub 2020 Jul 29. PMID: 32952391; PMCID: PMC7497793. 7: Yocum GT, Perez-Zoghbi JF, Danielsson J, Kuforiji AS, Zhang Y, Li G, Rashid Roni MS, Kodali R, Stafford DC, Arnold LA, Cook JM, Emala CW Sr. A novel GABAA receptor ligand MIDD0301 with limited blood-brain barrier penetration relaxes airway smooth muscle ex vivo and in vivo. Am J Physiol Lung Cell Mol Physiol. 2019 Feb 1;316(2):L385-L390. doi: 10.1152/ajplung.00356.2018. Epub 2018 Nov 29. PMID: 30489155; PMCID: PMC6397346. 8: Forkuo GS, Nieman AN, Kodali R, Zahn NM, Li G, Rashid Roni MS, Stephen MR, Harris TW, Jahan R, Guthrie ML, Yu OB, Fisher JL, Yocum GT, Emala CW, Steeber DA, Stafford DC, Cook JM, Arnold LA. A Novel Orally Available Asthma Drug Candidate That Reduces Smooth Muscle Constriction and Inflammation by Targeting GABAA Receptors in the Lung. Mol Pharm. 2018 May 7;15(5):1766-1777. doi: 10.1021/acs.molpharmaceut.7b01013. Epub 2018 Apr 2. Erratum in: Mol Pharm. 2019 Nov 4;16(11):4756. PMID: 29578347; PMCID: PMC5954213. 9: Webb DA, Meyer MJ, Medubi KM, Tylek AS, Yocum GT, Roni MSR, Zahn NM, Swartwout SA, Masoud AK, Emala CW, Stafford DC, Arnold LA. Design, Synthesis, and Biological Evaluation of Novel Spiro Imidazobenzodiazepines to Identify Improved Inhaled Bronchodilators. J Med Chem. 2023 Jul 27;66(14):9853-9865. doi: 10.1021/acs.jmedchem.3c00647. Epub 2023 Jul 7. PMID: 37418196; PMCID: PMC10833105. 10: Zahn NM, Roni MSR, Yocum GT, Meyer MJ, Webb DA, Mian MY, Cook JM, Stafford DC, Emala CW, Arnold LA. Development of Inhaled GABAA Receptor Modulators to Improve Airway Function in Bronchoconstrictive Disorders. ACS Pharmacol Transl Sci. 2022 Feb 1;5(2):80-88. doi: 10.1021/acsptsci.1c00238. PMID: 35187417; PMCID: PMC8844962.