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Basic Information

Molecular Structure:
CAS No.:	93479-97-1
Name:	Glimepiride
Article Data:	10

Formula:	C₂₄H₃₄N₄O₅S
Molecular Weight:	490.624
Synonyms:	glimepirid; hoe490
EINECS:	642-919-5
Density:	1.29 g/cm³
Melting Point:	212.2-214.5 °C
Solubility:	DMSO: >10 mg/mL
Appearance:	white cyrstalline solid
Hazard Symbols:	Xn,Xi
Risk Codes:	21-36/38-46-62-63
Safety:	25-26-36/37-53
PSA:	133.06000
LogP:	5.26540

Synthetic route

: 32175-00-1
(1R,4R)-1-isocyanato-4-methylcyclohexane

: 119018-29-0
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide

: 93479-97-1
glimepiride

Conditions

Conditions	Yield
Stage #1: (1R,4R)-1-isocyanato-4-methylcyclohexane; N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide With potassium carbonate In acetonitrile at 50 - 60℃; for 6h; Stage #2: With water at 70 - 75℃; for 4h;

: 766-36-9
3-ethyl-4-methyl-3-pyrrolin-2-one

: 93479-97-1
glimepiride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene / 2 h / 120 - 130 °C / Industrial scale 2.1: chlorosulfonic acid / dichloromethane / -5 - 30 °C 3.1: ammonium hydroxide / methanol / 2 h / 20 - 30 °C / Industrial scale 4.1: potassium carbonate / acetonitrile / 6 h / 50 - 60 °C 4.2: 4 h / 70 - 75 °C View Scheme

: 1943-82-4
phenethyl isocyanate

: 93479-97-1
glimepiride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene / 2 h / 120 - 130 °C / Industrial scale 2.1: chlorosulfonic acid / dichloromethane / -5 - 30 °C 3.1: ammonium hydroxide / methanol / 2 h / 20 - 30 °C / Industrial scale 4.1: potassium carbonate / acetonitrile / 6 h / 50 - 60 °C 4.2: 4 h / 70 - 75 °C View Scheme

: 247098-18-6
3-ethyl-4-methyl-2-oxo-N-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide

: 93479-97-1
glimepiride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / dichloromethane / -5 - 30 °C 2.1: ammonium hydroxide / methanol / 2 h / 20 - 30 °C / Industrial scale 3.1: potassium carbonate / acetonitrile / 6 h / 50 - 60 °C 3.2: 4 h / 70 - 75 °C View Scheme

Raw Materials

32175-00-1

119018-29-0

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Chemistry

Empirical Formula: C₂₄H₃₄N₄O₅S
Molecular Weight: 490.6156
Index of Refraction: 1.599
Molar Refractivity: 129.42 cm³
Molar Volume: 378.8 cm³
Surface Tension: 58.2 dyne/cm
Density: 1.29 g/cm³
Melting point: 212.2-214.5 °C
Storage tempreture: Room temp
Solubility: DMSO: >10 mg/mL
Sensitive: Moisture sensitive
Appearance: White cyrstalline solid
Structure of Glimepiride (CAS NO.93479-97-1):

IUPAC Name: 4-Ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl] ethyl]-5-oxo-2H-pyrrole-1-carboxamide
Canonical SMILES: CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)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
Product Category of Glimepiride (CAS NO.93479-97-1): Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Monovalent Ion Channels;Potassium Channel Modulators;Voltage-gated Ion Channels

Uses

Glimepiride (CAS NO.93479-97-1) is a sulfonylurea hypoglycemic agent, and is used as an antidiabetic.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	oral	28ug/kg/2D-I (0.028mg/kg)	BLOOD: HEMORRHAGE BLOOD: THROMBOCYTOPENIA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Annals of Pharmacotherpy. Vol. 34, Pg. 120, 2000.
mouse	LD50	unreported	> 10gm/kg (10000mg/kg)		Diabetes Frontier. Vol. 3, Pg. 565, 1992.
rat	LD	intraperitoneal	> 3950mg/kg (3950mg/kg)	LIVER: OTHER CHANGES	Arzneimittel-Forschung. Drug Research. Vol. 43, Pg. 547, 1993.
rat	LD	oral	> 10gm/kg (10000mg/kg)	LIVER: OTHER CHANGES	Arzneimittel-Forschung. Drug Research. Vol. 43, Pg. 547, 1993.
rat	LD50	unreported	> 10gm/kg (10000mg/kg)		Diabetes Frontier. Vol. 3, Pg. 565, 1992.

Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 21-36/38-46-62-63
R21:Harmful in contact with skin.
R36/38:Irritating to eyes and skin.
R46:May cause heritable genetic damage.
R62:Risk of impaired fertility.
R63:Possible risk of harm to the unborn child.
Safety Statements: 25-26-36/37-53
S25:Avoid contact with eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S53:Avoid exposure - obtain special instructions before use.
WGK Germany: 3
RTECS: UX9363950

Standards and Recommendations

APPEARANCE: white to yellowish crystalline powder
ASSAY (HPLC): 99.0% min
LOSS ON DRYING: 0.5% max
TOTAL IMPURITY: 1.0% max
HEAVY METALS: 20ppm max

Specification

Glimepiride , its cas register number is 93479-97-1. It also can be called 1-[[p-[2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea ; Amary ; and Glista OD . It is the first third-generation sulfonylurea, and is very potent. With Glimepiride (CAS NO.93479-97-1) GI absorption is complete, with no interference of meals.