3D Mol Similar

Gliquidone

: Iupac Name：1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea; CAS No.: 33342-05-1; Molecular Weight：527.636; Modify Date.: 2022-11-22 16:59; Introduction: It is a kind of hypoglycemic agents and can be used for the treatment of non-insulin-dependent diabetes. View more+

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1. Names and Identifiers

: 1.1 Name; Gliquidone; 1.2 Synonyms; ,4-dimethyl-1,3-dioxo-2(1h)-isoquinolinyl)ethyl)- 1-Cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl]urea 1-Cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea AR-DF 26 ARDF 26SE ardf26 ardf26se Beglynor Benzenesulfonamide, N-[(cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]- benzenesulfonamide,n-((cyclohexylamino)carbonyl)-4-(2-(3,4-dihydro-7-methoxy-4 Gliquidone Tablets Glurenorm N-[(Cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide TangShenPing TangShiPing ZINC 01482077 ZINC 1482077; View all

1.3 CAS No.: 33342-05-1

1.4 CID: 91610

1.5 EINECS(EC#): 251-463-2

1.6 Molecular Formula: C27H33N3O6S (isomer)

1.7 Inchi: InChI=1S/C27H33N3O6S/c1-27(2)23-14-11-20(36-3)17-22(23)24(31)30(25(27)32)16-15-18-9-12-21(13-10-18)37(34,35)29-26(33)28-19-7-5-4-6-8-19/h9-14,17,19H,4-8,15-16H2,1-3H3,(H2,28,29,33)

1.8 InChIkey: LLJFMFZYVVLQKT-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1(C2=C(C=C(C=C2)OC)C(=O)N(C1=O)CCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C

1.10 Isomers Smiles: CC1(C2=C(C=C(C=C2)OC)C(=O)N(C1=O)CCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C

2. Properties

2.1 Density: 1.34

2.1 Melting point: 179 °C

2.1 Boiling point: °Cat760mmHg

2.1 Refractive index: 1.624

2.1 Flash Point: °C

2.1 Precise Quality: 527.20900

2.1 PSA: 130.26000

2.1 logP: 5.31900

2.1 Appearance: Solid

2.2 Color/Form: Powder

2.3 Physical: Solid

2.4 pKa: 5.12±0.10(Predicted)

2.5 Water Solubility: 69.5 [ug/mL]

3. Use and Manufacturing

3.1 Methods of Manufacturing: Isoquinoline (30 g, 74.6 mmol), solvent 2, 5-dimethyltetrahydrofuran (300 mL) and anhydrous potassium carbonate (21 g, 151.9 mmol) were sequentially added to a 500 mL reaction flask. Open the stirring and heating, incubated at 40 °C for 30 minutes, and then slowly added cyclohexyl isocyanate (11.2g, 89.5mmol), the control was added dropwise over about 30 minutes after completion of the dropping temperature was raised, 90 °C Heated to reflux for 4 hours. The solvent 2, 5_ dimethyltetrahydrofuran was recovered under reduced pressure to give a white solid. To the reaction flask was added 200mL water, hydrochloric acid was slowly added dropwise to adjust PH = 3, cooled to 0-5 °C and stirred for 1 hour, filtered to give crude gliquidone, a yield of 98percent. The resulting gliquidone crude product into 5L of the three-necked flask to the bottle was added 3L of methanol, heated to 40 °C, the system was added ammonia / methanol, adjust the pH to 3, the gliquidone Crude product completely dissolved, and then continue to add 3g of neutral alumina and 3g silica gel (200-300 mesh), the use of alumina with silica gel completely adsorbed impurities in the system. 40 °C under stirring for 2 hours, filtered, the filtrate was adjusted with 3 M hydrochloric acid PH = 3, lower the temperature, 0-5 °C under agitation crystallization 4 hours. Filter, filter cake were washed with water, ethanol. 40 °C under vacuum for 12 hours to give a white granular solid, that is, gliquidone. Purity 99.75percent, yield 80percent.; View all

3.2 Usage: It is a kind of hypoglycemic agents and can be used for the treatment of non-insulin-dependent diabetes.

4. Safety and Handling

4.1 Safety Statements: 24/25

4.1 RTECS: DB1584250

4.1 Safety: Low toxicity by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NO_x and SO_x.
Safety information of Gliquidone (33342-05-1):
RTECS DB1584250

4.2 Toxicity

orl-mus LD50:>15 g/kg

USXXAM United States Patent Document. (Commissioner of Patents and Trademarks, Washington, DC 20231) #3708486 .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. Other Information

6.0 Mesh: Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

6.1 Biological Half Life: The mean terminal half-life was approximately 8 hours (range 5.7-9.4 hours)

6.2 Mesh Entry Terms: AR-DF 26

6.3 Merck: 14,4443

6.4 Diabetes: Diabetes is a group of syndrome of carbohydrate, fat, water and electrolyte metabolic disorder caused by the interaction of genetic and environmental factors, absolute or relative lack of insulin, and reduced cellular insulin sensitivity. According to the suggestion of ADA (in 1997) and WHO (in 1999), the diabetes are divided into four types, namely type 1 diabetes, type 2 diabetes, other specific types, and gestational diabetes. The vast majority belongs to type 2 diabetes (non-insulin-dependent diabetes mellitus, NIDDM), type 1 diabetes (insulin-dependent, IDDM) accounted for only 10% to 15%. The main clinical manifestations: polydipsia, polyphagia, polyuria, weight loss, fatigue, etc., advanced case is often accompanied with cataracts, abnormal reflexes in depth of feeling, urinary retention and skin infections. Type 1 " three polys and one little " is more obvious and is susceptible; the majority of patients with type 2 have no typical performances and is mainly in the form of complications or complications. Common complication mainly includes diabetic ketoacidosis and diabetic nonketotic hyperosmotic syndrome.; View all

6.5 Side effects: This product can be well tolerated. There is rare case of hypoglycemia during the treatment. There are only individual cases of patients who get gastrointestinal symptoms and skin allergy. Rare symptoms also include rash, jaundice, liver damage, bone marrow suppression, neutropenia, thrombocytopenia psychosis.

6.6 Precautions: 1. Only 5% of this product is excreted through the kidneys. Therefore, for patients of diabetes with mild to moderate renal insufficiency, it is significantly better to adopt gliquidone rather than other sulfonylurea drug. However, for patients of severe renal dysfunction, insulin is still appropriate. Patients of pregnancy and those who are allergic to sulfonylureas, patients of insulin-dependent diabetes mellitus, patients of pre-coma and coma of diabetes, diabetic patients with acidosis or ketosis should be banned.
2. Children and lactating women should apply with caution. During medication, elderly should start from small dose and gradually adjust the dose.
3. In case of hypoglycemia reaction, the patients should immediately have carbohydrates diet. If hypoglycemia continues, the patients should consider discontinuing.

6.7 Uses: It is a kind of hypoglycemic agents and can be used for the treatment of non-insulin-dependent diabetes.

6.8 Uses: Antidiabetic

6.9 Hazard: Low toxicity by ingestion. A reproductive hazard.

7. Computational chemical data

Molecular Weight: 527.636g/mol
Molecular Formula: C₂₇H₃₃N₃O₆S
Compound Is Canonicalized: True
XLogP3-AA: 4.6
Exact Mass: 527.20900695
Monoisotopic Mass: 527.20900695
Complexity: 948
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 130
Heavy Atom Count: 37
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB7OABAAAAAAAAAAAAAAAAAAAAAAAA8YMEAAAAAAACxQAAAHgQQQAAADizB2AYzB4PABAKIAiFSEHDCCBAkIAAIiJkODMiMJjKEtRuEMShk1jOIqYe6y9CPsAABAAAQAABgAAIAACAAAAAAAAAAAA==

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