Product Name

  • Name

    Glipizide

  • EINECS 249-427-6
  • CAS No. 29094-61-9
  • Article Data12
  • CAS DataBase
  • Density 1.34 g/cm3
  • Solubility methanol: 1.9 mg/mL
  • Melting Point 208-209 °C
  • Formula C21H27N5O4S
  • Boiling Point
  • Molecular Weight 445.542
  • Flash Point
  • Transport Information
  • Appearance crystalline solid
  • Safety 24/25-53-36/37-26-25
  • Risk Codes 21-36/38-46-62-63
  • Molecular Structure Molecular Structure of 29094-61-9 (Glipizide)
  • Hazard Symbols IrritantXi,HarmfulXn
  • Synonyms Glucotrol;Glydiazinamide;Prestwick_242;N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-pyrazine-2-carboxamide;Pyrazinecarboxamide,N-[2-[4-[[[(cyclohexylamino) carbonyl]amino]sulfonyl]phenyl]- ethyl]-5-methyl-;TK 1320;Glucotrol (TN);(Glipizide);
  • PSA 138.53000
  • LogP 4.33160

Synthetic route

carbon monoxide
201230-82-2

carbon monoxide

C14H16N4O3S*NaCl

C14H16N4O3S*NaCl

cyclohexylamine
108-91-8

cyclohexylamine

glipizide
29094-61-9

glipizide

Conditions
ConditionsYield
With iron(III)-acetylacetonate In methanol at 20 - 30℃; for 6h;85%
N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea
2015-16-9

N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea

5-methylpyrazine-2-carboxylic acid methyl ester
41110-33-2

5-methylpyrazine-2-carboxylic acid methyl ester

glipizide
29094-61-9

glipizide

Conditions
ConditionsYield
With water; sodium methylate In methanol at 85℃; Concentration; Temperature; Solvent;84%
ethyl cellulose

ethyl cellulose

1-ethenyl-2-pyrrolidinone
88-12-0

1-ethenyl-2-pyrrolidinone

glipizide
29094-61-9

glipizide

4-(2-aminoethyl)benzenesulfonamide
35303-76-5

4-(2-aminoethyl)benzenesulfonamide

glipizide
29094-61-9

glipizide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N,N-dimethyl-formamide / 4 h / 20 °C
2: potassium carbonate / acetone / 3 h / 50 - 55 °C
3: hydrogenchloride / methanol / 3 h / 50 - 55 °C
4: sodium methylate; water / methanol / 85 °C
View Scheme
tert-butyl (4-sulfamoyl phenethyl)carbamate
258262-54-3

tert-butyl (4-sulfamoyl phenethyl)carbamate

glipizide
29094-61-9

glipizide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 3 h / 50 - 55 °C
2: hydrogenchloride / methanol / 3 h / 50 - 55 °C
3: sodium methylate; water / methanol / 85 °C
View Scheme
tert-butyl (4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)carbamate

tert-butyl (4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)carbamate

glipizide
29094-61-9

glipizide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol / 3 h / 50 - 55 °C
2: sodium methylate; water / methanol / 85 °C
View Scheme
glipizide
29094-61-9

glipizide

N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide
33288-71-0

N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide

Conditions
ConditionsYield
With 3-azapentane-1,5-diamine at 120℃; for 6h; Sealed tube;89%
With dmap; phthalic anhydride In pyridine for 5h; Reflux; Inert atmosphere;63%
With pyridine; dmap; phthalic anhydride for 5h; Inert atmosphere; Reflux;63%
acetic anhydride
108-24-7

acetic anhydride

glipizide
29094-61-9

glipizide

N-<4-<2-(5-Methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>acetamid

N-<4-<2-(5-Methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>acetamid

Conditions
ConditionsYield
With pyridine for 0.25h;73%
diethylenetriaminepentaacetic dianhydride
23911-26-4

diethylenetriaminepentaacetic dianhydride

glipizide
29094-61-9

glipizide

DTPA-glipizide
848488-95-9

DTPA-glipizide

Conditions
ConditionsYield
Stage #1: glipizide With sodium amide In dimethyl sulfoxide at 20℃; for 0.166667h;
Stage #2: diethylenetriaminepentaacetic dianhydride With sodium amide In dimethyl sulfoxide at 20℃; for 4.16667h;
61.7%
glipizide
29094-61-9

glipizide

A

N-Cyclohexyl-N',N''-bis-<4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>guanidin

N-Cyclohexyl-N',N''-bis-<4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>guanidin

B

N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide
33288-71-0

N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride Heating;A 60%
B 17%
water
7732-18-5

water

cobalt(II) chloride
7646-79-9

cobalt(II) chloride

glipizide
29094-61-9

glipizide

C42H56CoN10O10S2

C42H56CoN10O10S2

Conditions
ConditionsYield
Reflux;54.16%
zirconium(II) nitrate

zirconium(II) nitrate

glipizide
29094-61-9

glipizide

C42H52N10O8S2Zr

C42H52N10O8S2Zr

Conditions
ConditionsYield
Reflux;52.14%
dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

glipizide
29094-61-9

glipizide

N,N'-Dicyclohexyl-N''-<4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>guanidin

N,N'-Dicyclohexyl-N''-<4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>guanidin

Conditions
ConditionsYield
With pyridine Heating;52%
succinic acid anhydride
108-30-5

succinic acid anhydride

glipizide
29094-61-9

glipizide

N-Cyclohexyl-N'-4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl-bernsteinsaeurediamid

N-Cyclohexyl-N'-4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl-bernsteinsaeurediamid

Conditions
ConditionsYield
With pyridine; dmap35%
diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

glipizide
29094-61-9

glipizide

N,N'-Diisopropyl-N''-<4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>guanidin

N,N'-Diisopropyl-N''-<4-<2-(5-methyl-2-pyrazincarboxamido)ethyl>benzolsulfonyl>guanidin

Conditions
ConditionsYield
With pyridine Heating;21%
tert-butyl peroxyacetate
107-71-1

tert-butyl peroxyacetate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

glipizide
29094-61-9

glipizide

A

N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-3,5-dimethylpyrazine-2-carboxamide trifluoroacetate

N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-3,5-dimethylpyrazine-2-carboxamide trifluoroacetate

B

N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-3,5,6-trimethylpyrazine-2-carboxamide trifluoroacetate

N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-3,5,6-trimethylpyrazine-2-carboxamide trifluoroacetate

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile at 30℃; Inert atmosphere; Irradiation;A 21%
B 21%
β‐cyclodextrin
7585-39-9

β‐cyclodextrin

glipizide
29094-61-9

glipizide

2C21H27N5O4S*C42H70O35

2C21H27N5O4S*C42H70O35

Conditions
ConditionsYield
In methanol; water for 0.75h; Kneading;
β‐cyclodextrin
7585-39-9

β‐cyclodextrin

glipizide
29094-61-9

glipizide

C21H27N5O4S*C42H70O35
468055-52-9

C21H27N5O4S*C42H70O35

Conditions
ConditionsYield
In methanol; water for 0.75h; Kneading;
β‐cyclodextrin
7585-39-9

β‐cyclodextrin

glipizide
29094-61-9

glipizide

C21H27N5O4S*2C42H70O35

C21H27N5O4S*2C42H70O35

Conditions
ConditionsYield
In methanol; water for 0.75h; Kneading;
β‐cyclodextrin
7585-39-9

β‐cyclodextrin

glipizide
29094-61-9

glipizide

C21H27N5O4S*3C42H70O35

C21H27N5O4S*3C42H70O35

Conditions
ConditionsYield
In methanol; water for 0.75h; Kneading;
piperazine
110-85-0

piperazine

glipizide
29094-61-9

glipizide

glipizide*piperazine

glipizide*piperazine

Conditions
ConditionsYield
In methanol for 0.333333h;
glipizide
29094-61-9

glipizide

N-(4-(N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)sulfamoyl)phenethyl)-5-methylpyrazine-2-carboxamide

N-(4-(N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)sulfamoyl)phenethyl)-5-methylpyrazine-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap; phthalic anhydride / pyridine / 5 h / Reflux; Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil
2.2: 15 h / 20 °C / Inert atmosphere
View Scheme

Glipizide Chemical Properties

Molecular Structure of Glipizide (CAS NO.29094-61-9):

IUPAC Name:N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-5-methylpyrazine-2-carboxamide
Molecular Formula: C21H27N5O4S
Molecular Weight: 445.535180 g/mol
Appearance: white solid
Melting Point: 208-209°C
H bond acceptors: 9
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 112.16Å2
Index of Refraction: 1.615
Molar Refractivity: 115.92 cm3
Molar Volume: 331.8 cm3
Surface Tension: 66.8 dyne/cm
Density: 1.34 g/cm3
Solubility: methanol 1.9 mg/mL
Categories: Intermediates & Fine Chemicals; Pharmaceuticals; API's; Potassium channel

Glipizide Safety Profile

Safety Information of  Glipizide (CAS NO.29094-61-9):
Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 21-36/38-46-62-63
21:Harmful in contact with skin
36/38:Irritating to eyes and skin 
46:May cause heritable genetic damage
62:Possible risk of impaired fertility 
63:Possible risk of harm to the unborn child 
Safety Statements: 24/25-53-36/37-26-25
24/25:Avoid contact with skin and eyes
53:Avoid exposure - obtain special instruction before use
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
25:Avoid contact with eyes    
WGK Germany: 3
RTECS: YS7640000
F: 10

Glipizide Specification

  Glipizide , with CAS number of 29094-61-9, can be called 2-pyrazinecarboxamide, N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl- ; N-(2-{4-[(Cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-5-methyl-2-pyrazinecarboxamide ; Pyrazinecarboxamide, N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-5-methyl- . Glipizide (CAS NO.29094-61-9) is an oral medium-to-long acting anti-diabetic drug.

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