Acarbose information

Acarbose
Clinical data
Trade names	Glucobay, Precose, Prandase
Other names	(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5- {[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl- 5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3- (hydroxymethyl)cyclohex-2-en-1-yl]amino} tetrahydro-2H-pyran-2-yl]oxy}-3,4-dihydroxy- 6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}- 6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol
AHFS/Drugs.com	Monograph
MedlinePlus	a696015
License data	US DailyMed: Acarbose;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
ATC code	A10BF01 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Extremely low
Metabolism	Gastrointestinal tract
Elimination half-life	2 hours
Excretion	Kidney (less than 2%)
Identifiers
	IUPAC name O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose;
CAS Number	56180-94-0 ;
PubChem CID	444254;
IUPHAR/BPS	6791;
DrugBank	DB00284 ;
ChemSpider	392239 ;
UNII	T58MSI464G;
KEGG	D00216 ;
ChEMBL	ChEMBL1566 ;
CompTox Dashboard (EPA)	DTXSID8046034 ;
ECHA InfoCard	100.054.555
Chemical and physical data
Formula	C25H43NO18
Molar mass	645.608 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O([C@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@@H]1CO)[C@H]4O[C@@H]([C@@H](O[C@H]3O[C@H](C)[C@@H](N[C@H]2/C=C(/CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]3O)[C@H](O)[C@H]4O)CO;
	InChI InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12-,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-/m1/s1 ; Key:XUFXOAAUWZOOIT-SXARVLRPSA-N ;
	(verify)

Acarbose (INN)^[1]^[2] is an anti-diabetic drug used to treat diabetes mellitus type 2 and, in some countries, prediabetes. It is a generic sold in Europe and China as Glucobay (Bayer AG), in North America as Precose (Bayer Pharmaceuticals), and in Canada as Prandase (Bayer AG).

Acarbose is a starch blocker. It works by inhibiting alpha glucosidase, an intestinal enzyme that releases glucose from larger carbohydrates such as starch and sucrose. It is composed of an acarviosin moiety with a maltose at the reducing terminus. It can be degraded by a number of gut bacteria.^[3]

Acarbose is cheap and popular in China, but not in the U.S. One physician explains that use in the U.S. is limited because it is not potent enough to justify the side effects of diarrhea and flatulence.^[4] However, a large study concluded in 2013 that "acarbose is effective, safe and well tolerated in a large cohort of Asian patients with type 2 diabetes."^[5] A possible explanation for the differing opinions is an observation that acarbose is significantly more effective in patients eating a relatively high carbohydrate Eastern diet.^[6]

^ Elks J, Ganellin CR, eds. (1990). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1–. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2085-3.
^ "International Nonproprietary Names for Pharmaceutical Substances. Recommended International Nonproprietary Names (Rec. INN): List 19" (PDF). World Health Organization. 1979. Retrieved 9 November 2016.
^ Cite error: The named reference :0 was invoked but never defined (see the help page).
^ Kresge N (21 November 2011). "China's Thirst for New Diabetes Drugs Threatens Bayer's Lead". Bloomberg Business Week. Archived from the original on 21 November 2011. Retrieved 15 April 2016.
^ Zhang W, Kim D, Philip E, Miyan Z, Barykina I, Schmidt B, Stein H (April 2013). "A multinational, observational study to investigate the efficacy, safety and tolerability of acarbose as add-on or monotherapy in a range of patients: the Gluco VIP study". Clinical Drug Investigation. 33 (4): 263–274. doi:10.1007/s40261-013-0063-3. PMID 23435929. S2CID 207483590.
^ Zhu Q, Tong Y, Wu T, Li J, Tong N (June 2013). "Comparison of the hypoglycemic effect of acarbose monotherapy in patients with type 2 diabetes mellitus consuming an Eastern or Western diet: a systematic meta-analysis". Clinical Therapeutics. 35 (6): 880–899. doi:10.1016/j.clinthera.2013.03.020. PMID 23602502.

[1] Elks J, Ganellin CR, eds. (1990). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1–. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2085-3.

[INN-2] "International Nonproprietary Names for Pharmaceutical Substances. Recommended International Nonproprietary Names (Rec. INN): List 19" (PDF). World Health Organization. 1979. Retrieved 9 November 2016.

[:0-3] Cite error: The named reference :0 was invoked but never defined (see the help page).

[4] Kresge N (21 November 2011). "China's Thirst for New Diabetes Drugs Threatens Bayer's Lead". Bloomberg Business Week. Archived from the original on 21 November 2011. Retrieved 15 April 2016.

[5] Zhang W, Kim D, Philip E, Miyan Z, Barykina I, Schmidt B, Stein H (April 2013). "A multinational, observational study to investigate the efficacy, safety and tolerability of acarbose as add-on or monotherapy in a range of patients: the Gluco VIP study". Clinical Drug Investigation. 33 (4): 263–274. doi:10.1007/s40261-013-0063-3. PMID 23435929. S2CID 207483590.

[6] Zhu Q, Tong Y, Wu T, Li J, Tong N (June 2013). "Comparison of the hypoglycemic effect of acarbose monotherapy in patients with type 2 diabetes mellitus consuming an Eastern or Western diet: a systematic meta-analysis". Clinical Therapeutics. 35 (6): 880–899. doi:10.1016/j.clinthera.2013.03.020. PMID 23602502.

Acarbose information

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