Product Name

  • Name

    Gliclazide

  • EINECS 244-260-5
  • CAS No. 21187-98-4
  • Article Data10
  • CAS DataBase
  • Density 1.35 g/cm3
  • Solubility soluble in methylene chloride
  • Melting Point 163-169 °C(lit.)
  • Formula C15H21N3O3S
  • Boiling Point
  • Molecular Weight 323.416
  • Flash Point
  • Transport Information
  • 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-;
  • PSA 86.89000
  • LogP 3.43030

Synthetic route

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

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

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
With N,N-dimethyl-formamide In toluene for 2h; Reagent/catalyst; Reflux;91.9%
3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride
58108-05-7

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

4-toluenesulfonylurea
1694-06-0

4-toluenesulfonylurea

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
In toluene for 3h; Reflux;86%
phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

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

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
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

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

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
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

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

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
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

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

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
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

N-amino-1,2-cyclopentanedicarboximide

gliclazide
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

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

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
With Simulated Gastric Fluid at 37℃; for 2h; pH=1.2; Time;
N-amino-aza-3-bicyclo<3.3.0>octane
54528-00-6

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

gliclazide
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
gliclazide
21187-98-4

gliclazide

copper dichloride

copper dichloride

C30H44CuN6O6S2

C30H44CuN6O6S2

Conditions
ConditionsYield
Reflux;74%
gliclazide
21187-98-4

gliclazide

water
7732-18-5

water

Co metal salt solution

Co metal salt solution

C30H48CoN6O8S2

C30H48CoN6O8S2

Conditions
ConditionsYield
Reflux;70%
...Expand
gliclazide
21187-98-4

gliclazide

zinc(II) chloride
7646-85-7

zinc(II) chloride

C30H40N6O6S2Zn

C30H40N6O6S2Zn

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 3h; pH=6 - 6.5; Reflux;53.16%
gliclazide
21187-98-4

gliclazide

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride
58108-05-7

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

Conditions
ConditionsYield
With chloride ions In various solvent(s) at 37℃; for 24h; Product distribution; various concentrations of anions and cations, with and without human serum proteins;
gliclazide
21187-98-4

gliclazide

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

C15H21N3O3S*C6N4

C15H21N3O3S*C6N4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.5h;
1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

gliclazide
21187-98-4

gliclazide

C15H21N3O3S*C10H18O4

C15H21N3O3S*C10H18O4

Conditions
ConditionsYield
In acetone at 20℃; for 1h;
glycolic Acid
79-14-1

glycolic Acid

gliclazide
21187-98-4

gliclazide

C15H21N3O3S*C2H4O3

C15H21N3O3S*C2H4O3

Conditions
ConditionsYield
In acetone at 20℃; for 1h;
4-aminopyridine
504-24-5

4-aminopyridine

gliclazide
21187-98-4

gliclazide

gliclazide-4-aminopyridine salt

gliclazide-4-aminopyridine salt

Conditions
ConditionsYield
In diethyl ether; ethanol for 168h;
3,4-diaminopyridine
54-96-6

3,4-diaminopyridine

gliclazide
21187-98-4

gliclazide

gliclazide-3,4-aminopyridine salt

gliclazide-3,4-aminopyridine salt

Conditions
ConditionsYield
In diethyl ether; ethanol for 336h;
gliclazide
21187-98-4

gliclazide

benzene-1,2-diol
120-80-9

benzene-1,2-diol

gliclazide*catechol

gliclazide*catechol

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 3h;
gliclazide
21187-98-4

gliclazide

recorcinol
108-46-3

recorcinol

gliclazide*resorcinol

gliclazide*resorcinol

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 3h;
piperazine
110-85-0

piperazine

gliclazide
21187-98-4

gliclazide

gliclazide*piperazine

gliclazide*piperazine

Conditions
ConditionsYield
In methanol for 0.333333h;
gliclazide
21187-98-4

gliclazide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

gliclazide*p-toluenesulfonic acid

gliclazide*p-toluenesulfonic acid

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 0.333333h;
gliclazide
21187-98-4

gliclazide

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

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

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 100℃;
gliclazide
21187-98-4

gliclazide

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

GZD-AMP salt

GZD-AMP salt

Conditions
ConditionsYield
In methanol; water
gliclazide
21187-98-4

gliclazide

2C15H21N3O3S*I(1+)*I3(1-)

2C15H21N3O3S*I(1+)*I3(1-)

Conditions
ConditionsYield
With iodine In methanol; chloroform at 20℃; for 24h;
gliclazide
21187-98-4

gliclazide

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

C15H21N3O3S*C6H3N3O7

C15H21N3O3S*C6H3N3O7

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 24h;
gliclazide
21187-98-4

gliclazide

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

C15H21N3O3S*C8Cl2N2O2

C15H21N3O3S*C8Cl2N2O2

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 24h;
In acetonitrile at 20℃; for 2h;
gliclazide
21187-98-4

gliclazide

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

hydrogen cyanide
74-90-8

hydrogen cyanide

B

4-methyl-N-(1-(1,2,2-tricyanovinyl)hexahydropenta[c]pyrrol-2-(1H)-ylcarbamoyl)benzenesulfonamide

4-methyl-N-(1-(1,2,2-tricyanovinyl)hexahydropenta[c]pyrrol-2-(1H)-ylcarbamoyl)benzenesulfonamide

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 24h;
...Expand
gliclazide
21187-98-4

gliclazide

3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone
87-88-7

3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone

C15H21N3O3S*C6H2Cl2O4

C15H21N3O3S*C6H2Cl2O4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2h;

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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