ACARBOSE

ACARBOSE

The structural formula

Brief background information

MF C 25 H 43 NO 18

MW 645.61 g / mol

cas   56180-94-0

Acarbose, Bay-g-5421, Prandase, Glucor, Precose, Glucobay

O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-alpha-D-glucopyranosyl-(1--4)-O-alpha-D-glucopyranosyl-(1--4)-D-glucose; O-4,6-Dideoxy-4-[[[1S-(1alpha,4alpha,5beta,6alpha)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-c

Acarbose is an anti-diabetic drug used to treat type 2 diabetes mellitus and, in some countries, prediabetes. It is an inhibitor of alpha glucosidase, an enteric enzyme that releases glucose from larger carbohydrates. 

The total synthesis of acarbose has been reported. Condensation 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (I) with the protected 1,6-anhydromaltose (II) in the presence of trimethylsilyl triflate gave trisaccharide (III) as a mixture of 
epimers at position 1". Hydrogenolysis of the desired isomer using Pd/C furnished the debenzylated trisaccharide (IV). After conversion of (IV) to the corresponding 
nona-acetate and chromatographic purification, deacetylation with sodium methoxide in MeOH afforded 1,6-anhydromaltotriose (V).

http://www.chemdrug.com/databases/8_0_pcrgfloeixammedx.html

Application

• antidiabetic
• an inhibitor of α-glucosidase
• hypoglycemic

Classes of substances

• Carbohydrates, amino derivatives

Synthesis pathway

Synthesis a)
Produced by fermentation of Actinoplanes SE50 / 110

Trade Names

Country	Trade name	Manufacturer
Germany	Glucobay	Bayer
France	Glyukor	- "-
United Kingdom	Glucobay	- "-
Italy	Glikobaz	- "-
Japan	Glucobay	- "-
USA	Prekoz	- "-
Ukraine	Glucobay	Helsker Bayer AG, Germany  Bayer AG, Germany
	Alumina	ABDI IBRAHIM Ilach Sanayi ve Ticaret AS, Turkey

Formulations

• Tablets of 50 mg, 100 mg

UV - spectrum

Conditions : Concentration - 5 mg / 100 ml
Solvent designation schedule	Methanol	Water	0.1 M HCl	0.1M NaOH
The absorption maximum	-	-	-	-
	-	-	-	-
ε	-	-	-	-

IR - spectrum

Wavelength (μm)
Wavenumber (cm -1 )

NMR Spectrum

WILL BE ADDED

Links

• US 4,062,950 (Bayer; 13.12.1977; D-prior. 22.9.1973).
• DOS 2,347,782 (Bayer; appl. 21.9.1973).
• Schmidt, DD et al .: Naturwissenschaften (NATWAY) 64, 535 (1977).

• UV and IR Spectra. H.-W. Dibbern, RM Muller, E. Wirbitzki, 2002 ECV
• NIST / EPA / NIH Mass Spectral Library 2008
• Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman.Academic Press, 2000.
• Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.