Glimepiride - Moligand™, ≥99% , CAS No.93479-97-1

CAS: 93479-97-1 Cat. No.: G129354 Molecular Weight: 490.62 EC Number: 642-919-5

GRADE & PURITY Moligand™, ≥99%

Synonyms

CCRIS 7083 | GLIMEPIRIDE [USP-RS] | HMS2097C03 | HMS3677K06 | 24T6XIR2MZ | BPBio1_000751 | Glimepiride (JP17/USP/INN) | Glista OD | HOE 490 | SMR000466368 | GLIMEPIRIDE [USP MONOGRAPH] | Glimepiride Impurity A | HMS3714C03 | Glimepiride- Bio-X | Glymepiri

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Glimepiride is a third generation sulfonylurea compound, which increases the release of insulin from pancreatic beta cells. In addition, Glimepiride increases the activity of intracellular insulin receptors. Studies conducted on adipocytes and skeletal muscle suggest that Glimepiride induces the PI3 kinase (PI3K) and Akt pathway, along with insulin receptor substrate-1/2 and endothelial nitric oxide synthase. Glimepiride also increases osteoblast proliferation and differentiation, which is thought to be related to its ability to activate the PI3K and Akt pathway. Furthermore, Glimepiride enhances intrinsic peroxisome proliferator-activated receptor γ activity. Glimepiride also increases protein expression of glucose transports 1 and 4, and is a potent KIR channel blocker.
A third generation sulfonylurea compound that induces the PI3K and Akt pathway

Specifications

Synonyms

CCRIS 7083 | GLIMEPIRIDE [USP-RS] | HMS2097C03 | HMS3677K06 | 24T6XIR2MZ | BPBio1_000751 | Glimepiride (JP17/USP/INN) | Glista OD | HOE 490 | SMR000466368 | GLIMEPIRIDE [USP MONOGRAPH] | Glimepiride Impurity A | HMS3714C03 | Glimepiride- Bio-X | Glymepiri

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Potent cardiac K ir 6 (K ATP ) channel blocker (IC 50 = 6.8 nM). Antidiabetic agent. Orally active and active in vivo .

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504750676
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750676
• Canonical Smiles: CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
• IUPAC Name: 4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide
• InChIKey: WIGIZIANZCJQQY-UHFFFAOYSA-N
• INCHI: 1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)
• Isomeric SMILES: CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
• WGK Germany: 3
• RTECS: UX9363950
• Molecular Weight: 490.62
• Reaxy-Rn: 5365754
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5365754&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzenesulfonamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzenesulfonamides
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzenesulfonamides
• Alternative Parents: Benzenesulfonyl compounds Sulfonylureas N-acyl ureas Pyrrolines Organosulfonic acids and derivatives Aminosulfonyl compounds Isoureas Propargyl-type 1,3-dipolar organic compounds Carboxylic acids and derivatives Carboximidamides Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzenesulfonamide - Benzenesulfonyl group - N-acyl urea - Sulfonylurea - Ureide - Pyrroline - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Isourea - Carboximidic acid derivative - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP2C9 Tchem Cytochrome P450 2C9 (0 Activities)

Discover Target: CYP2C9

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in DMSO (>10 mg/ml), water (<1 mg/ml at 25 °C), and ethanol (<1 mg/ml at 25 °C).
• Melt Point(°C): 204 °C
• Molecular Weight: 490.600 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 490.225 Da
• Monoisotopic Mass: 490.225 Da
• Topological Polar Surface Area: 133.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 895.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zixian He, Zhiwei Liu, Haihuan Xie, Pengjie Luo, Xiangmei Li.  (2023)  An Ultrasensitive Lateral Flow Immunoassay Based on Metal-Organic Framework-Decorated Polydopamine for Multiple Sulfonylureas Adulteration in Functional Foods.  Foods,  12  (3): (539).  [PMID:36766067] [10.3390/foods12030539]

2. Haihuan Xie, Yingying Li, Jin Wang, Yi Lei, Anastasios Koidis, Xiangmei Li, Xing Shen, Zhenlin Xu, Hongtao Lei.  (2021)  Broad-specific immunochromatography for simultaneous detection of various sulfonylureas in adulterated multi-herbal tea.  FOOD CHEMISTRY,      [PMID:34536782] [10.1016/j.foodchem.2021.131055]

3. Jiankun Cao, Qing Jiang, Ruixian Li, Qian Xu, Hongli Li.  (2019)  Nanofibers mat as sampling module of direct analysis in real time mass spectrometry for sensitive and high-throughput screening of illegally adulterated sulfonylureas in antidiabetic health-care teas.  TALANTA,      [PMID:31357362] [10.1016/j.talanta.2019.06.066]

4. Fu Jian-Fang, Ren Qin-You, Zhang Nan-Yan, Gao Bin, Tu Yan-Yang, Fu Guo-Qiang, Li Dao-Hai, Zhang Yong-Sheng.  (2012)  Inhibition potential of glimepiride (gli) towards important UDP-glucuronosyltransferase (UGT) isoforms in human liver.  PHARMAZIE,  67  (8): (715-717).  [PMID:] [10.1691/ph.2012.1851]