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Basic Information
| CAS No.: | 21187-98-4 |
|---|---|
| Name: | Gliclazide |
| Article Data: | 10 |
| Molecular Structure: | |
|
|
|
| Formula: | C15H21N3O3S |
| Molecular Weight: | 323.416 |
| 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.) |
| Solubility: | soluble in methylene chloride |
| Appearance: | white cyrstalline solid |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 21-36/38-46-62-63 |
| Safety: | 25-26-36/37-53 |
| PSA: | 86.89000 |
| LogP: | 3.43030 |
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Synthetic route
- 70-55-3
toluene-4-sulfonamide
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| In toluene for 3h; Reflux; | 86% |
- 70-55-3
toluene-4-sulfonamide
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 70-55-3
toluene-4-sulfonamide
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 70-55-3
toluene-4-sulfonamide
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 70-55-3
toluene-4-sulfonamide
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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 |
- 21187-98-4
gliclazide
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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 |
Conditions
| Conditions | Yield |
|---|---|
| Reflux; | 74% |
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Gliclazide
Chemistry
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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:
Xn,
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: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
Xn,XiRisk 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 .