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93479-97-1 molecular structure
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3-ethyl-4-methyl-N-{2-[4-({[(4-methylcyclohexyl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide

ChemBase ID: 107
Molecular Formular: C24H34N4O5S
Molecular Mass: 490.61556
Monoisotopic Mass: 490.22499121
SMILES and InChIs

SMILES:
S(=O)(=O)(NC(=O)NC1CCC(CC1)C)c1ccc(CCNC(=O)N2CC(=C(C2=O)CC)C)cc1
Canonical SMILES:
CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCC(CC1)C
InChI:
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)
InChIKey:
WIGIZIANZCJQQY-UHFFFAOYSA-N

Cite this record

CBID:107 http://www.chembase.cn/molecule-107.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-ethyl-4-methyl-N-{2-[4-({[(4-methylcyclohexyl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
IUPAC Traditional name
amaryl
Brand Name
Amarel
Amaryl
Endial
Novo-glimepiride
PMS-glimepiride
Ratio-glimepiride
Sandoz glimepiride
Synonyms
Glimepirid
Glimepirida
Glimepiridum
Glimepride
Glimepiride
CAS Number
93479-97-1
PubChem SID
46508842
160963570
PubChem CID
3476

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00222 external link
PubChem 3476 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.3201776  H Acceptors
H Donor LogD (pH = 5.5) 2.3483384 
LogD (pH = 7.4) 2.180386  Log P 3.1205344 
Molar Refractivity 129.8042 cm3 Polarizability 50.725914 Å3
Polar Surface Area 124.68 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.82  LOG S -4.11 
Solubility (Water) 3.84e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Insoluble expand Show data source
Hydrophobicity(logP)
3.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00222 external link
Item Information
Drug Groups approved
Description Glimepiride is the first III generation sulphonyl urea it is a very potent sulphonyl urea with long duration of action.
Indication For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
Pharmacology Glimepiride, like glyburide and glipizide, is a "second-generation" sulfonylurea agents. Glimepiride is used with diet to lower blood glucose by increasing the secretion of insulin from pancreas and increasing the sensitivity of peripheral tissues to insulin.
Toxicity Severe hypoglycemic reactions with coma, seizure, or other neurological impairment.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Following either an intravenous or oral dose, glimepiride is completely metabolized by oxidative biotransformation to a major metabolite, cyclohexyl hydroxymethyl derivative (M1), via the hepatic cytochrome P450 II C9 subsystem. M1 is further metabolized to the carboxyl derivative (M2) by one or several cytosolic enzymes. M1, but not M2, possessed approximately one third of the pharmacologic activity of its parent in an animal model. However, whether the glucose-lowering effect of M1 is clinically significant is not clear.
Absorption Completely (100%) absorbed following oral administration.
Half Life Approximately 5 hours following single dose.
Protein Binding Over 99.5% bound to plasma protein.
Distribution * 21.8 ± 13.9 L [Volunteers]
* 19.8 ± 12.7 L [Patients with Type 2 diabetes, Single Dose]
* 37.1 ± 18.2 L [Patients with Type 2 diabetes, Multiple Dose]
Clearance * 52.1 +/- 16.0 mL/min [Normal subjects with single oral dose]
* 48.5 +/- 29.3 mL/min [Patients with Type 2 diabetes, with single oral dose]
* 52.7 +/- 40.3 mL/min [Patients with Type 2 diabetes, with multiple oral dose]
* 47.8 mL/min [healthy after intravenous (IV) dosing]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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