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21187-98-4

Basic Information
CAS No.: 21187-98-4
Name: Gliclazide
Molecular Structure:
Molecular Structure of 21187-98-4 (Gliclazide)
Formula: C15H21N3O3S
Molecular Weight: 323.41
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-;
EINECS: 244-260-5
Density: 1.35 g/cm3
Melting Point: 163-169 °C(lit.)
Boiling Point:
Flash Point:
Solubility: soluble in methylene chloride
Appearance: white cyrstalline solid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 21-36/38-46-62-63
Safety: 25-26-36/37-53
Transport Information:
PSA: 86.89000
LogP: 3.43030
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%
21187-98-4

gliclazide

Co metal salt solution

Co metal salt solution

C30H48CoN6O8S2

Conditions
ConditionsYield
Reflux;70%
21187-98-4

gliclazide

7646-85-7

zinc(II) chloride

C30H40N6O6S2Zn

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

gliclazide

A

70-55-3

toluene-4-sulfonamide

B

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;
21187-98-4

gliclazide

670-54-2

ethenetetracarbonitrile

C15H21N3O3S*C6N4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.5h;
111-20-6

1,10-decanedioic acid

21187-98-4

gliclazide

C15H21N3O3S*C10H18O4

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

glycolic Acid

21187-98-4

gliclazide

C15H21N3O3S*C2H4O3

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

4-aminopyridine

21187-98-4

gliclazide

gliclazide-4-aminopyridine salt

Conditions
ConditionsYield
In diethyl ether; ethanol for 168h;
54-96-6

3,4-diaminopyridine

21187-98-4

gliclazide

gliclazide-3,4-aminopyridine salt

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

gliclazide

120-80-9

benzene-1,2-diol

gliclazide*catechol

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

gliclazide

108-46-3

recorcinol

gliclazide*resorcinol

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

piperazine

21187-98-4

gliclazide

gliclazide*piperazine

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

gliclazide

104-15-4

toluene-4-sulfonic acid

gliclazide*p-toluenesulfonic acid

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

gliclazide

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

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

gliclazide

156-87-6

propan-1-ol-3-amine

GZD-AMP salt

Conditions
ConditionsYield
In methanol; water
21187-98-4

gliclazide

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

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

gliclazide

88-89-1

2,4,6-Trinitrophenol

C15H21N3O3S*C6H3N3O7

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

gliclazide

84-58-2

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

C15H21N3O3S*C8Cl2N2O2

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

gliclazide

670-54-2

ethenetetracarbonitrile

A

74-90-8

hydrogen cyanide

B

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

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

gliclazide

87-88-7

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

C15H21N3O3S*C6H2Cl2O4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2h;
Downstream Products
58108-05-7
70-55-3
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    Product name:Gliclazide Molecular Formula: C15H21N3O3S Molecular Weight: 323.41 CAS No.: 21187-98-4 EINECS: 244-260-5 Function: Anti-diabetic drug Grade: CP,EP,BP Certificate: GMP Appearance:White powder Storage:Store in cool and dr

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Chemistry


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

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.

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.

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

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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