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Acarbose

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-A3013

  • Specification : 98%

  • CAS number : 56180-94-0

  • Formula : C25H43NO18

  • Molecular Weight : 645.6

  • PUBCHEM ID : 41774

  • Volume : 25mg

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Catalogue Number

BF-A3013

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

645.6

Appearance

White needle crystal

Botanical Source

Structure Type

Carbohydrates

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C=C(C(C(C4O)O)O)CO

Synonyms

β-D-Glucopyranose, 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)-/Acarbose/(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-dihydro/BAY-g 5421/(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/4,6-Dideoxy-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino}-α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-β-D-glucopyranose/O-4,6-Dideoxy-4-[[[1S-(1a,4a,5b,6a)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-(1®4)-O-a-D-glucopyranosyl-(1®4)-D-glucose/Ascarbose/acarviostatin I01/Bay g 5421/4",6"-dideoxy-4"-[(1 S )-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino]maltotriose/(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-dihydro/(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/4,6-Dideoxy-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}-α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-β-D-glucopyranose/bay-g5421/Prandase/Precose/Glucobay/Precos

IUPAC Name

(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]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol

Density

1.7±0.1 g/cm3

Solubility

Methanol; Water; DMSO

Flash Point

541.4±34.3 °C

Boiling Point

971.6±65.0 °C at 760 mmHg

Melting Point

165-170ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2940000000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:56180-94-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

12086760

Abstract

BACKGROUND:
The worldwide increase in type 2 diabetes mellitus is becoming a major health concern. We aimed to assess the effect of acarbose in preventing or delaying conversion of impaired glucose tolerance to type 2 diabetes.

METHODS:
In a multicentre, placebo-controlled randomised trial, we randomly allocated patients with impaired glucose tolerance to 100 mg acarbose or placebo three times daily. The primary endpoint was development of diabetes on the basis of a yearly oral glucose tolerance test (OGTT). Analyses were by intention to treat.

FINDINGS:
We randomly allocated 714 patients with impaired glucose tolerance to acarbose and 715 to placebo. We excluded 61 (4%) patients because they did not have impaired glucose tolerance or had no postrandomisation data. 211 (31%) of 682 patients in the acarbose group and 130 (19%) of 686 on placebo discontinued treatment early. 221 (32%) patients randomised to acarbose and 285 (42%) randomised to placebo developed diabetes (relative hazard 0.75 [95% CI 0.63-0.90]; p=0.0015). Furthermore, acarbose significantly increased reversion of impaired glucose tolerance to normal glucose tolerance (p<0.0001). At the end of the study, treatment with placebo for 3 months was associated with an increase in conversion of impaired glucose tolerance to diabetes. The most frequent side-effects to acarbose treatment were flatulence and diarrhoea.

INTERPRETATION:
Acarbose could be used, either as an alternative or in addition to changes in lifestyle, to delay development of type 2 diabetes in patients with impaired glucose tolerance.

Comment in
Acarbose delays onset of type 2 diabetes mellitus. [J Fam Pract. 2002]
Acarbose for type 2 diabetes prevention. [Lancet. 2002]
Acarbose for type 2 diabetes prevention. [Lancet. 2002]

Title

Acarbose for prevention of type 2 diabetes mellitus: the STOP-NIDDM randomised trial.

Author

Chiasson JL1, Josse RG, Gomis R, Hanefeld M, Karasik A, Laakso M; STOP-NIDDM Trail Research Group.

Publish date

2002 Jun 15

PMID

28234967

Abstract

In this work, we investigated the effect of pH on Streptomyces M37 growth and its acarbose biosynthesis ability. We observed that low pH was beneficial for cell growth, whereas high pH favored acarbose synthesis. Moreover, addition of glucose and maltose to the fermentation medium after 72 h of cultivation promoted acarbose production. Based on these results, a two-stage fermentation strategy was developed to improve acarbose production. Accordingly, pH was kept at 7.0 during the first 72 h and switched to 8.0 after that. At the same time, glucose and maltose were fed to increase acarbose accumulation. With this strategy, we achieved an acarbose titer of 6210 mg/L, representing an 85.7% increase over traditional batch fermentation without pH control. Finally, we determined that the increased acarbose production was related to the high activity of glutamate dehydrogenase and glucose 6-phosphate dehydrogenase.

Title

Enhanced acarbose production by Streptomyces M37 using a two-stage fermentation strategy.

Author

Ren F1,2,3, Chen L2, Xiong S3, Tong Q2.

Publish date

2017 Feb 24

PMID

32200914

Abstract

BACKGROUND:
Acarbose and repaglinide are two safe and effective antidiabetic agents that are especially in wide use in Asian and Middle Eastern countries. These two prandial agents share some outstanding qualities that their newer counterparts do not. While globally available in generic versions, both are oral and cheap. There is a paucity of data regarding their comparative efficacy. Herein, a head-to-head comparison of the efficacy of the two in treatment of postprandial hyperglycemia of newly-diagnosed type 2 diabetes was investigated.

MATERIALS AND METHODS:
One hundred and sixty-four newly-diagnosed type 2 diabetes patients with fasting plasma glucose levels of <7.2 mmol/L (130 mg/dL) but 2-hour postprandial glucose (2hPPG) levels of >10 mmol/L (180 mg/dL) were consecutively alternated between acarbose- and repaglinide-treatment for 6 months.

RESULTS:
Per protocol analysis, 67% of acarbose-treated patients versus 85% of repaglinide-treated patients achieved 2hPPG levels of <10 mmol/L (180 mg/dL) (P = 0.05). Treatment adherence rates were 52.4% and 72%, respectively (P < 0.02). Thirteen of the repaglinide-treated and 2 of acarbose-treated patients reported at least one episode of hypoglycemia (P < 0.03). Fasting plasma glucose, 2hPPG, glycated hemoglobin and basal insulin requirement decreased more significantly with repaglinde than acarbose (P, <0.05, <0.04, <0.04 and <0.03, respectively). Weight increased with repaglinide and decreased with acarbose (P = 0.03). There were no significant changes in LDL levels with either treatment (P = 0.58), but triglycerides decreased more significantly with acarbose treatment (P = 0.03) CONCLUSIONS: Significantly higher rates of treatment-adherence and at-target glycemic levels were seen with repaglinide treatment. Weight decreased with acarbose and increased with repaglinide treatment. Hypoglycemic episodes were much less frequent with acarbose treatment.

Copyright © 2020 Southern Society for Clinical Investigation. Published by Elsevier Inc. All rights reserved.

KEYWORDS

Acarbose; Cost considerations; Postprandial hyperglycemia; Repaglinide; Treatment adherence; Type 2 diabetes

Title

Acarbose versus Repaglinide in Diabetes Treatment: A New Appraisal of Two Old Rivals.

Author

Pishdad R1, Pishdad P2, Pishdad GR3.

Publish date

2020 Apr


Description :

Acarbose is an inhibitor of alpha glucosidase, an anti-diabetic drug.