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Gliclazide
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Name

Gliclazide

 EINECS 244-260-5
CAS No. 21187-98-4 Density 1.35 g/cm3
PSA 86.89000 LogP 3.43030
Solubility soluble in methylene chloride Melting Point 163-169 °C(lit.)
Formula C15H21N3O3S Boiling Point N/A
Molecular Weight 323.416 Flash Point N/A
Transport Information N/A Appearance white cyrstalline solid
Safety 25-26-36/37-53 Risk Codes 21-36/38-46-62-63
Molecular Structure Molecular Structure of 21187-98-4 (Gliclazide) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

Urea,1-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)- (8CI);Cyclopenta[c]pyrrole, benzenesulfonamide deriv.;1-(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea;Diabezidum;Diabyl;Diamicron;Diaprel;Glimicron;Glinormax;Glyzide;N-(4-Methylbenzenesulfonyl)-N'-[3-azabicyclo(3,3,0)oct-3-yl]urea;S1702;S 852;SE 1702;Benzenesulfonamide,N-[[(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-methyl-;

Article Data 10

Gliclazide Synthetic route

N-(hexahydrocyclopenta[c]pyrrole-2-(1H)-yl)aminocarbonyl chloride

70-55-3

toluene-4-sulfonamide

21187-98-4

gliclazide

Conditions
ConditionsYield
With N,N-dimethyl-formamide In toluene for 2h; Reagent/catalyst; Reflux;91.9%
58108-05-7

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride

1694-06-0

4-toluenesulfonylurea

21187-98-4

gliclazide

Conditions
ConditionsYield
In toluene for 3h; Reflux;86%

phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

70-55-3

toluene-4-sulfonamide

21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h; Reagent/catalyst; Solvent;		70%

p-methoxyphenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

70-55-3

toluene-4-sulfonamide

21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: p-methoxyphenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h;		60%

p-fluorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

70-55-3

toluene-4-sulfonamide

21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: p-fluorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h;		52%

p-chlorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

70-55-3

toluene-4-sulfonamide

21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: p-chlorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h;		40%

N-amino-1,2-cyclopentanedicarboximide

21187-98-4

gliclazide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; pyrographite; ruthenium(III) chloride trihydrate; hydrogen / water / 16 h / 140 °C / 60006 Torr / Autoclave
2: hydrogenchloride
3: toluene / 3 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; hydrogen / 4 h / 80 °C / 15001.5 Torr / Autoclave
2: N,N-dimethyl-formamide / dichloromethane / 3 h / 50 °C / 4500.45 Torr / Autoclave; Inert atmosphere
3: N,N-dimethyl-formamide / toluene / 2 h / Reflux
View Scheme

N-[N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-N'-hydroxycarbamimidoyl]-4-methylbenzenesulfonamide

21187-98-4

gliclazide

Conditions
ConditionsYield
With Simulated Gastric Fluid at 37℃; for 2h; pH=1.2; Time;
54528-00-6

N-amino-aza-3-bicyclo<3.3.0>octane

21187-98-4

gliclazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-heptane / 1 h / 0 - 25 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 3 h / 100 °C
2.2: 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-heptane / 1 h / 0 - 25 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 3 h / 100 °C
2.2: 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-heptane / 1 h / 0 - 25 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 3 h / 100 °C
2.2: 2 h / 25 °C
View Scheme
21187-98-4

gliclazide

copper dichloride

C30H44CuN6O6S2

Conditions
ConditionsYield
Reflux;74%

Gliclazide Chemical Properties


IUPAC Name: 1-(3,3a,4,5,6,6a-Hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea 
Empirical Formula: C15H21N3O3S
Molecular Weight: 323.4105
Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2
InChI: InChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)
InChIKey: BOVGTQGAOIONJV-UHFFFAOYSA-N
EINECS: 244-260-5
Product Categories: Pharmaceutical; Active Pharmaceutical Ingredients; APIs; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Potassium channel 
Index of Refraction: 1.623
Molar Refractivity: 84.41 cm3
Molar Volume: 239.2 cm3
Surface Tension: 60.4 dyne/cm
Density: 1.35 g/cm3 
Appearance: White Cyrstalline Solid
Melting Point: 163-169 °C(lit.)
solubility: methylene chloride: soluble
Classification Code of Gliclazide (CAS NO.21187-98-4): Drug / Therapeutic Agent; Human Data; Hypoglycemic agents; Reproductive Effect

Gliclazide Uses

 Gliclazide is used for control of hyperglycemia in gliclazide-responsive diabetes mellitus of stable, mild, non-ketosis prone, maturity-onset or adult type. It is used when diabetes cannot be controlled by proper dietary management and exercise or when insulin therapy is not appropriate.

Gliclazide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 17, Pg. 81, 1982.
mouse LD50 intravenous 295mg/kg (295mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 2661, 1980.
mouse LD50 oral 3gm/kg (3000mg/kg)   Indian Drugs. Vol. 15, Pg. 161, 1978.
mouse LD50 subcutaneous 1034mg/kg (1034mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 2661, 1980.
rat LD50 intravenous 382mg/kg (382mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 2661, 1980.
rat LD50 oral 3gm/kg (3000mg/kg)   Indian Drugs. Vol. 15, Pg. 161, 1978.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 2661, 1980.
women TDLo oral 9600ug/kg/24D (9.6mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED		 Internal Medicine. Vol. 33, Pg. 163, 1994.

Gliclazide Safety Profile

Hazard Codes:HarmfulXn,IrritantXi
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:Possible 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 instruction before use
WGK Germany:2
RTECS:YT4500000

Gliclazide Specification

 Gliclazide (CAS NO.21187-98-4), its Synonyms are 1-(3-Azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea ; 1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea ; Benzenesulfonamide, N-(((hexahydrocyclopenta(c)pyrrol-2(1H)-yl)amino)carbonyl)-4-methyl- ; Diamicron ; Glimicron ; N-(4-Methylbenzenesulfonyl)-N'-(3-azabicyclo(3.3.0)oct-3-yl)urea ; Nordialex .
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