Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-06 15:16:52 UTC |
---|
Update Date | 2022-03-07 02:51:58 UTC |
---|
HMDB ID | HMDB0015381 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Gliquidone |
---|
Description | Gliquidone, also known as glurenorm or beglynora, belongs to the class of organic compounds known as 1,3-isoquinolinediones. These are isoquinoline derivatives carrying one C=O group at positions 1, and 3 respectively. It is classified as a second-generation sulfonylurea. Gliquidone is a drug which is used in the treatment of diabetes mellitus type 2. Gliquidone is an extremely weak basic (essentially neutral) compound (based on its pKa). It is used in the treatment of diabetes mellitus type 2. It is marketed by the pharmaceutical company Boehringer Ingelheim (Germany). Its metabolites are excreted virtually completely with bile (even with long-term administration), thus allowing the use of medication in diabetic patients suffering from kidney disease and diabetic nephropathy. Allergy to sulfonylureas or sulfonamidesDiabetes mellitus type 1Diabetic ketoacidosisPatients that underwent removal of the pancreasAcute porphyriaSevere liver disease accompanying with liver insufficiencySeveral conditions (e.g., infectious diseases or major surgical intervention), when insulin administration is requiredPregnancy or breastfeedingGliquidone is fully metabolized by the liver. Gliquidone (INN, sold under the trade name Glurenorm) is an anti-diabetic medication in the sulfonylurea class. |
---|
Structure | COC1=CC2=C(C=C1)C(C)(C)C(=O)N(CCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)C2=O 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) |
---|
Synonyms | Value | Source |
---|
Glurenorm | Kegg | Sanofi synthelabo brand OF gliquidone | HMDB | Glikvidon | HMDB | Gliquidone, monosodium salt | HMDB | AR-DF 26 | HMDB | Beglynora | HMDB | Yamanouchi brand OF gliquidone | HMDB | Beglynor | HMDB | Glurenor | HMDB | Gliquidone, calcium salt | HMDB | Glycvidon | HMDB | N'-cyclohexyl-N-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}carbamimidate | HMDB | N'-cyclohexyl-N-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulphonyl}carbamimidate | HMDB | N'-cyclohexyl-N-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulphonyl}carbamimidic acid | HMDB |
|
---|
Chemical Formula | C27H33N3O6S |
---|
Average Molecular Weight | 527.632 |
---|
Monoisotopic Molecular Weight | 527.209006493 |
---|
IUPAC Name | 1-cyclohexyl-3-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}urea |
---|
Traditional Name | gliquidone |
---|
CAS Registry Number | 33342-05-1 |
---|
SMILES | COC1=CC2=C(C=C1)C(C)(C)C(=O)N(CCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)C2=O |
---|
InChI Identifier | 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) |
---|
InChI Key | LLJFMFZYVVLQKT-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as 1,3-isoquinolinediones. These are isoquinoline derivatives carrying one C=O group at positions 1, and 3 respectively. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Isoquinolines and derivatives |
---|
Sub Class | 1,3-isoquinolinediones |
---|
Direct Parent | 1,3-isoquinolinediones |
---|
Alternative Parents | |
---|
Substituents | - 1,3-isoquinolinedione
- Isoquinolone
- Tetrahydroisoquinoline
- Benzenesulfonamide
- Benzenesulfonyl group
- Anisole
- Alkyl aryl ether
- Sulfonylurea
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid imide, n-substituted
- Carboxylic acid imide
- Dicarboximide
- Aminosulfonyl compound
- Sulfonyl
- Organosulfonic acid or derivatives
- Organic sulfonic acid or derivatives
- Carboximidic acid derivative
- Carboxylic acid derivative
- Azacycle
- Organic 1,3-dipolar compound
- Ether
- Propargyl-type 1,3-dipolar organic compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Organosulfur compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 181 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0022 g/L | Not Available | LogP | 4.5 | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Gliquidone,1TMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC3CCCCC3)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 4146.0 | Semi standard non polar | 33892256 | Gliquidone,1TMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC3CCCCC3)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 3864.4 | Standard non polar | 33892256 | Gliquidone,1TMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC3CCCCC3)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 5634.9 | Standard polar | 33892256 | Gliquidone,1TMS,isomer #2 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C3CCCCC3)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 4104.5 | Semi standard non polar | 33892256 | Gliquidone,1TMS,isomer #2 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C3CCCCC3)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 3921.3 | Standard non polar | 33892256 | Gliquidone,1TMS,isomer #2 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C3CCCCC3)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 5540.4 | Standard polar | 33892256 | Gliquidone,2TMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C3CCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 3951.0 | Semi standard non polar | 33892256 | Gliquidone,2TMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C3CCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 4112.7 | Standard non polar | 33892256 | Gliquidone,2TMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C3CCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C1)C(=O)C2(C)C | 5326.5 | Standard polar | 33892256 | Gliquidone,1TBDMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC3CCCCC3)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 4429.2 | Semi standard non polar | 33892256 | Gliquidone,1TBDMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC3CCCCC3)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 4068.1 | Standard non polar | 33892256 | Gliquidone,1TBDMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)NC3CCCCC3)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 5629.7 | Standard polar | 33892256 | Gliquidone,1TBDMS,isomer #2 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C3CCCCC3)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 4372.7 | Semi standard non polar | 33892256 | Gliquidone,1TBDMS,isomer #2 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C3CCCCC3)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 4149.9 | Standard non polar | 33892256 | Gliquidone,1TBDMS,isomer #2 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)NC(=O)N(C3CCCCC3)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 5529.5 | Standard polar | 33892256 | Gliquidone,2TBDMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C3CCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 4464.7 | Semi standard non polar | 33892256 | Gliquidone,2TBDMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C3CCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 4555.5 | Standard non polar | 33892256 | Gliquidone,2TBDMS,isomer #1 | COC1=CC=C2C(=C1)C(=O)N(CCC1=CC=C(S(=O)(=O)N(C(=O)N(C3CCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C(=O)C2(C)C | 5311.1 | Standard polar | 33892256 |
| Show more...
---|