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Acetohexamide

CAT: 0804-HY-B0881-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-B0881-02Size:10 mM - 1 mL
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Description
Acetohexamide is an orally active first-generation sulfonylurea agent used in research related to type 2 diabetes and cancer. Acetohexamide exerts reductase activity in human erythrocytes. Acetohexamide stimulates the pancreas to secrete insulin. Acetohexamide inhibits ATP-sensitive potassium channels in the β cells of the pancreas. Acetohexamide can inhibit the formation of circular chemorepellent induced defects (CCIDs) in lymphendothelial cell (LEC) monolayers. Acetohexamide inhibits markers of epithelial-to-mesenchymal-transition and migration. Acetohexamide suppresses the synthesis of 12 (S) -HETE. Acetohexamide can potentiate hypoglycaemic action[1][2][3][4].
CAS Number
968-81-0
UNSPSC
12352005
Hazard Statement
H302, H312, H332
Target
Potassium Channel
Type
Reference compound
Related Pathways
Membrane Transporter/Ion Channel
Applications
Cancer-programmed cell death
Field of Research
Metabolic Disease; Cancer
Assay Protocol
https://www.medchemexpress.com/Acetohexamide.html
Purity
99.67
Solubility
DMSO : 25 mg/mL (ultrasonic)
Smiles
O=S(C1=CC=C(C(C)=O)C=C1)(NC(NC2CCCCC2)=O)=O
Molecular Formula
C15H20N2O4S
Molecular Weight
324.40
Precautions
H302, H312, H332
References & Citations
[1]White JA, et al. Nonhypoglycemic drug reactions of agents used to treat diabetes. Endocrinol Metab Clin North Am. 2000 Dec;29 (4) :803-11.|[2]Kishimoto, M., et al., (1994) . Carbonyl reductase activity for acetohexamide in human erythrocytes. Drug metabolism and disposition: the biological fate of chemicals, 22 (3), 367–370.|[3]Kretschy, N., et al., (2013) . In vitro inhibition of breast cancer spheroid-induced lymphendothelial defects resembling intravasation into the lymphatic vasculature by acetohexamide, isoxsuprine, nifedipin and proadifen. British journal of cancer, 108 (3), 570–578.|[4]Imamura, Y., et al., (1990) . Mechanism of pharmacodynamic and pharmacokinetic interactions between acetohexamide and phenylbutazone in rabbits. Pharmacology & toxicology, 67 (5), 415–419.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Acetohexamide

Acetohexamide is an N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a p-acetylphenylsulfonyl group, while a hydrogen attached to the other nitrogen is replaced by a cyclohexyl group. It has a role as a hypoglycemic agent and an insulin secretagogue. It is a member of acetophenones and a N-sulfonylurea.

CAS Number968-81-0
PubChem CID1989
IUPAC Name1-(4-acetylphenyl)sulfonyl-3-cyclohexylurea
Molecular FormulaC15H20N2O4S
Molecular Weight324.4
XLogP2.4
Topological Polar Surface Area101
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Heavy Atom Count22
Formal Charge0
Complexity498
SMILES
CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2CCCCC2
InChI
InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
InChIKey
VGZSUPCWNCWDAN-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Acetohexamide
CAS: 968-81-0
CID: 1989
Formula: C15H20N2O4S
MW: 324.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight324.4
XLogP32.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass324.11437830
Monoisotopic Mass324.11437830
Topological Polar Surface Area101 Ų
Heavy Atom Count22
Formal Charge0
Complexity498
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
FA16951-01Acetohexamide
A17745-50Acetohexamide 50mg
A17745-100Acetohexamide 100mg
TRC-A162652-10MGAcetohexamide-d11
A17745-500Acetohexamide 500mg
A17745-10mM-DAcetohexamide 10mM * 1mL in DMSO

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