Name: Glibenclamide
SKU: 10238-21-8

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Basic Information

Molecular Structure:
CAS No.:	10238-21-8
Name:	Glibenclamide
Article Data:	26

Formula:	C₂₃H₂₈C_lN₃O₅S
Molecular Weight:	494.011
Synonyms:	Urea,1-[[p-[2-(5-chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-cyclohexyl- (8CI);1-[4-[2-(5-Chloro-2-methoxybenzamido)ethyl]phenylsulfonyl]-3-cyclohexylurea;Adiab;Antibet;Apo-Glibenclamide;Betanaz;Betanese 5;Calabren;Cytagon;Daonil;Daonil N;Debtan;Dia-basan;Diabeta;Diabiphage;Dibelet;Duraglucon;Euglucan;Euglucon;Euglucon 5;Euglykon;GBN 5;Gilemal;Gl;Glamide;Gliban;Gliben;Gliben-Puren N;Glibenclamide;Glibenil;Glibens;Glibesyn;Glibet;Glibetic;Glibil;Glibomet;Gliboral;Glicem;Glidiabet;Glucobene;Glucohexal;Glucolon;Glucomid;Glucoremed;Glucoven;Glukovital;Glyben;Glybenzcyclamide;Glycomin;HD 419;Hemi-Daonil;Libanil;Melix;N-4-[2-(5-Chloro-2-methoxybenzamido)ethyl]phenylsulfonyl-N'-cyclohexylurea;N-[4-[b-(2-Methoxy-5-chlorobenzamido)ethyl]benzenesulfonyl]-N'-cyclohexylurea;Orabetic;Pira;Prodiabet;Renabetic;Semi-Daonil;
EINECS:	233-570-6
Density:	1.36 g/cm³
Melting Point:	173-175 °C
Solubility:	Practically insoluble in water, sparingly soluble in methylene chloride, slightly soluble in ethanol (96%) and in methanol. Practically insoluble in ether. It dissolves in dilute solutions of alkali hydroxides.
Appearance:	white or almost white crystalline podwer
Hazard Symbols:	Xn
Risk Codes:	20/21/22
Safety:	22-36/37/39
PSA:	121.98000
LogP:	5.89520

Synthetic route

: 16673-34-0
5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide

: 3173-53-3
Cyclohexyl isocyanate

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
With copper(l) chloride In nitromethane at 20℃; for 2h; Reagent/catalyst; Solvent; Concentration; Milling;	100 %Spectr.
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Sealed tube;	81 mg
With 18-crown-6 ether; potassium tert-butylate In N,N-dimethyl-formamide at 0 - 5℃; for 6h; Reflux;	4.49 g

: 201230-82-2
carbon monoxide

: 4-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl azide

: 108-91-8
cyclohexylamine

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
With palladium diacetate In acetonitrile at 20℃; under 15 Torr; Schlenk technique; Sealed tube;	99%

...Expand

: C19H21ClN2O6S*C6H13N

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
In toluene at 110℃; Industrial scale;

: 3438-16-2
5-chloro-2-methoxybenzoic acid

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane / 12 h / 20 °C / Schlenk technique 2: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 3: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 5 steps 1: oxalyl dichloride / dichloromethane / 12 h / 20 °C / Schlenk technique 2: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 3: chlorosulfonic acid / 1,2-dichloro-ethane / 50 °C / Schlenk technique 4: sodium azide / acetonitrile / 50 °C / Schlenk technique 5: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 4 steps 1: phosphorus trichloride / tetrahydrofuran / 0.08 h / 150 °C / Sealed tube 2: chlorosulfonic acid / chloroform / 0.17 h / 60 °C / Sealed tube 3: ammonium hydroxide / 1,4-dioxane / 0.17 h / 120 °C / Sealed tube; Cooling with ice 4: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Sealed tube View Scheme

: 33924-49-1
DK13

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 1,2-dichloro-ethane / 50 °C / Schlenk technique 2: sodium azide / acetonitrile / 50 °C / Schlenk technique 3: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 3 steps 1: chlorosulfonic acid / chloroform / 0.17 h / 60 °C / Sealed tube 2: ammonium hydroxide / 1,4-dioxane / 0.17 h / 120 °C / Sealed tube; Cooling with ice 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Sealed tube View Scheme

: 64-04-0
phenethylamine

: 10238-21-8
Glibenclamid

Conditions

Yield

Multi-step reaction with 4 steps
1: phosphorus trichloride / tetrahydrofuran / 0.08 h / 150 °C / Sealed tube
2: chlorosulfonic acid / chloroform / 0.17 h / 60 °C / Sealed tube
3: ammonium hydroxide / 1,4-dioxane / 0.17 h / 120 °C / Sealed tube; Cooling with ice
4: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Sealed tube
View Scheme

Multi-step reaction with 5 steps
1.1: pyridine / tetrahydrofuran / 4 h / 20 °C / Cooling with ice
2.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
3.1: ammonium hydroxide / acetone / 20 °C
4.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
4.2: 16 h / 20 °C
5.1: potassium tert-butylate; 18-crown-6 ether / N,N-dimethyl-formamide / 6 h / 0 - 5 °C / Reflux
View Scheme

: 29568-33-0
2-methoxy-5-chlorobenzoyl chloride

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 2: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 2: chlorosulfonic acid / 1,2-dichloro-ethane / 50 °C / Schlenk technique 3: sodium azide / acetonitrile / 50 °C / Schlenk technique 4: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme

: 33924-54-8
4-(2-[(5-chloro-2-methoxyphenyl)formamido]ethyl)benzene-1-sulfonyl chloride

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / acetonitrile / 50 °C / Schlenk technique 2: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme

: 16673-34-0
5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium hydroxide / acetone / Industrial scale 2.1: pyrographite / acetone / 1.17 h / Reflux; Industrial scale 2.2: 0.5 h / 58 °C / Industrial scale 3.1: toluene / 110 °C / Industrial scale View Scheme

: 458-85-5
2,2,2-trifluoro-N-(2-phenylethyl)acetamide

: 10238-21-8
Glibenclamid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice 2.1: ammonium hydroxide / acetone / 20 °C 3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 3.2: 16 h / 20 °C 4.1: potassium tert-butylate; 18-crown-6 ether / N,N-dimethyl-formamide / 6 h / 0 - 5 °C / Reflux View Scheme

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Specification

The Glyburide has the cas register number 10238-21-8, and it is a kind of white crystalline powder. The IUPAC name and systematic name are the same which is 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide. This chemical is insoluble in water while slightly soluble in ethanol, acetone, chloroform, and its product categories are including Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organics; Amino Acids & Derivatis; Isotope Labeled Compounds; API's; Potassium channel; Ion Channels. When you neee to store it, keep it in a dry, cool and well-ventilated storeroom.

The physical properties of this chemical are as follows: (1)ACD/LogP: 3.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.58; (4)ACD/LogD (pH 7.4): 1.79; (5)ACD/BCF (pH 5.5): 27.82; (6)ACD/BCF (pH 7.4): 4.52; (7)ACD/KOC (pH 5.5): 173.93; (8)ACD/KOC (pH 7.4): 28.24; (9)#H bond acceptors: 8; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 95.61; (13)Index of Refraction: 1.616; (14)Molar Refractivity: 126.9 cm³; (15)Molar Volume: 362.9 cm³; (16)Polarizability: 50.3×10^-24cm³; (17)Surface Tension: 61.2 dyne/cm; (18)Density: 1.36 g/cm³; (19)Exact Mass: 493.143819; (20)MonoIsotopic Mass: 493.143819; (21)Topological Polar Surface Area: 122; (22)Heavy Atom Count: 33; (23)Formal Charge: 0; (24)Complexity: 746.

As to its usage, it is usually applied in pharmaceutics. It could be used as the hypoglycemicagent, with better curative effect than tolbutamide; It is often used in the curing of mild and moderate non-insulin-dependent diabetes mellitus.

When you are dealing with this kind of chemical, you should be much more careful and then take some measures to protect yourself. Being a kind of harmful chemical, it may cause damage to health. And if by inhalation, in contact with skin and if swallowed, you will be hurt by this chemical. Therefore, you should take the following instructions. Wear suitable protective clothing, gloves and eye/face protection while using and then do not breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
(2)InChI: InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-
10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
(3)InChIKey: ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Below are the toxicity information of this chemical:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	oral	> 10gm/kg (10000mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969.
guinea pig	LD50	oral	> 15gm/kg (15000mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969.
man	TDLo	oral	209mg/kg/4Y-I (209mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: "JAUNDICE, CHOLESTATIC" LIVER: OTHER CHANGES	Western Journal of Medicine. Vol. 168, Pg. 274, 1998.
mouse	LD50	intraperitoneal	2700mg/kg (2700mg/kg)		Pharmaceutical Chemistry Journal Vol. 29, Pg. 265, 1995.
mouse	LD50	oral	3250mg/kg (3250mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1640, 1966.
mouse	LD50	subcutaneous	> 20gm/kg (20000mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970.
rabbit	LD	oral	> 20gm/kg (20000mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970.
rat	LD50	intraperitoneal	3750mg/kg (3750mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
rat	LD50	oral	> 20gm/kg (20000mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
rat	LD50	subcutaneous	> 20gm/kg (20000mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
women	TDLo	oral	147ug/kg (0.147mg/kg)	BEHAVIORAL: COMA ENDOCRINE: HYPOGLYCEMIA	Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 142, 1984.

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Specification