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56180-94-0

56180-94-0 structure
56180-94-0 structure

Name acarbose
Synonyms Acbose API
roxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-d-glucopyranosyl-o
Acbos
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
MFCD00869592
O-4,6-Dideoxy-4-[[[1S-(1α,4α,5β,6α)]-4,5,6-trihydroxy-3-(hydroxyMethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-O-α-D-glucopyranosyl-D-glucose
acarviostatin I01
Acbose extrapure
Acboser
Acbose Hydrate
4",6"-dideoxy-4"-[(1 S )-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino]maltotriose
O-4,6-DIDEOXY-4-[[[1S-(1A,4A,5BETA,6A)]-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL]AMINO]-ALPHA-D-GLUCOPYRANOSYL-O-ALPHA-D-GLUCOPYRANOSYL-D-GLUCOSE
4)-O-a-D-glucopyranosyl-(1®
(2R,3R,4R,5S,6R)-5-((2R,3R,4R,5S,6R)-5
high qualtiy Acbose 5
O-4,6-Dideoxy-4-[[[1S-(1a,4a,5b,6a)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-O-a-D-glucopyranosyl-D-gluco- se
Acbose //BP
EINECS 260-030-7
Acbose Hydrate>
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
Bay g 5421:Glucobay
Ascarbose
ACBOSE DC ANULES
Bay g 5421
Acbose
AMylostatin J, Bay g 5421, alpha-GHI
Acbose for identification CRS
Acbose (1.0mg/ml in DMSO)
(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-méthyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxyméthyl)cyclohex-2-én-1-yl]amino}tétrahydro-2H-pyran-2-yl]oxy}-3,4-dihydro
Acbose 5
O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-O-α-D-glucopyranosyl-D-Glucose
d-glucose,o-4,6-dideoxy-4-(((1s-(1-alpha,4-alpha,5-beta,6-alpha))-4,5,6-trihyd
Acbose CRS
Acbose, alpha-glucosidase inhibitor
(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-(hydroxy methyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2, 3 4-trio
Acbose for peak identification CRS
(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
O-4,6-Dideoxy-4-[[[1S(1α,4α,5β,6α-)-4,5,6-trihydrDxy-3-(hydroxymethyl)-2-cyclohexen-1-y1]amino]- α-D-glucopyranosyl-(1→4)-O-α-D-ducopyranosyl-(1→4)-D-glucose
O-4,6-DIDEOXY-4-[[[1S-(1A,4A,5BETA,6A)]-4,5,6-TRIHYDROXY-3-(HYDROXYMETHY
Acbose 56-0
D-Glucose, O-4,6-dideoxy-4-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-, [1S-(1α,4α,5β,6α)]
AcboseQ: What is Acbose Q: What is the CAS Number of Acbose Q: What e the applications of Acbose
(2R,3R,4R,5R)-4-(((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)-2,3,5,6-tetrahydroxyhexanal
D-Glucose,O-4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxyMethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-(1®
Acbose (COLD SHIPMENT REQUIRED)
(3S,5S)-5-[(2R,3S,5S)-5-[(2R,3S,5S)-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
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
O-4,6-Dideoxy-4-[[[1S-(1a,4a,5,6a)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-O-a-D-glucopyranosyl-D-glucose
D-Glucose, 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)
Acbose Tablets
Precos
4-O-[4-O-[4-[[(1S,4R,5S,6S)-4,5,6-Trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-4,6-dideoxy-α-D-glucopyranosyl]-α-D-glucopyranosyl]-D-glucopyranose
A.3-aminopropane-1-sulfonicacid(homotaurine)
(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-(hydroxy methyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2, 3 4-triol
Ascbose
5-[5-[3,4-DIHYDROXY-6-METHYL-5-[[4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-1-CYCLOHEX-2-ENYL]AMINO]OXAN-2-YL]OXY-3,4-DIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY-6-(HYDROXYMETHYL)OXANE-2,3,4-TRIOL
(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-méthyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxyméthyl)cyclohex-2-én-1-yl]amino}tétrahydro-2H-pyran-2-yl]oxy}-3,4-dihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-6-(hydroxyméthyl)tétrahydro-2H-pyran-2,3,4-triol
Acbose fom Actinoplanes sp. ca. 100 FIP-AIU/mg
(2R,3R,4R,5R)-4-(((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)-2,3,5,6
4-[[5-[[3,4-dihydroxy-6-methyl-5-[[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-2,3,5,6-tetrahydroxyhexanal
Acbose (Acbosum)
(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
Acbose (Acbosum) (Mixture ofDiastereomers)
bay-g5421
alpha-d-glucopyranosyl
4",6"-Dideoxy-4"-([1S]-[1,4,6/5]-4,5,6-trihydroxy-3-hydroxymethyl-2-yclohexenylamino)-maltotriose
Prandase
Precose
Glucobay
Description Acarbose is an inhibitor of alpha glucosidase, an anti-diabetic drug.
Related Catalog
In Vitro Acarbose (1, 2, and 3 μM) dose- and time-dependently inhibits TNF-α-induced VSMC proliferation and migration. Acarbose (1, 2, and 3 μM) dose-dependently decreases β-galactosidase, Ras expression and increased p-AMPK expression in TNF-α pre-treated A7r5 cells[2].
In Vivo Acarbose (300 mg/60 kg body weight) decreases the fasting blood glucose, and regulates the glucose tolerance of DM rats without body weight loss. Acarbose significantly suppresses serum IL6 and TNF-α in DM rats[1]. Acarbose (2.5 and 5.0 mg/kg) significantly and dose-dependently decreases the intensity of neointimal IL-6, TNF-α, and iNOS staining, and significantly increases the intensity of neointimal p-AMPK staining. Acarbose (2.5 and 5.0 mg/kg) significantly and dose-dependently decreases neointimal Ras and β-galactosidase expression in HCD-fed rabbits without body weight loss[2].
Cell Assay Cell viability is determined using the MTT assay. Cells are seeded in 24-well culture plates at a density of 2×104 cells/well, incubated for 48 h, treated with acarbose at varying concentrations (0.5, 1.0, 2.0, 3.0, and 5.0 μM) for 24 h; or pre-treated with TNF-α (20 ng/mL) for either 24 h or 48 h to evaluate the dose-dependent effects of acarbose on VSMC growth and viability, cultured with 0.5 mg/mL MTT at 37°C in a humidified atmosphere of 5% CO2 for another 4 h, and solubilized with isopropanol. The viable cell number varies directly with the concentration of formazan product measured spectrophotometrically at 563 nm.
Animal Admin Twenty-four male New Zealand white rabbits, weighing 2500 g are used. They are individually housed in metal cages in an air-conditioned room (22 ± 2°C, 55 ± 5% humidity), under a 12 h light/12 h dark cycle with free access to food and water. All rabbits are randomLy assigned to four groups of 6 animals each and are fed either standard chow (Group I), high cholesterol diet (HCD; containing 95.7% standard Purina chow + 3% lard oil + 0.5% cholesterol) (Group II), HCD diet and 2.5 mg/kg per day acarbose (Group III), or HCD diet and 5.0 mg/kg per day acarbose (Group IV). At the end of the 25 weeks, all rabbits are sacrificed by exsanguination under deep anesthesia with pentobarbital (30 mg/kg i.v.) injected via the marginal ear vein. Serum is stored at −80°C prior to measurement of serum values. The aortic arch and thoracic aortas are carefully removed to protect the endothelial lining, and are collected and freed of adhering soft tissue.
References

[1]. Zhang Q, et al. Acarbose Reduces Blood Glucose by Activating miR-10a-5p and miR-664 in Diabetic Rats. PLoS One. 2013 Nov 18;8(11):e79697.

[2]. Chan KC, et al. Pleiotropic effects of acarbose on atherosclerosis development in rabbits are mediated via upregulating AMPK signals. Sci Rep. 2016 Dec 7;6:3864

Density 1.7±0.1 g/cm3
Boiling Point 971.6±65.0 °C at 760 mmHg
Melting Point 165-170ºC
Molecular Formula C25H43NO18
Molecular Weight 645.605
Flash Point 541.4±34.3 °C
Exact Mass 645.247986
PSA 321.17000
LogP -4.16
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.689

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LZ7153000
CHEMICAL NAME :
D-Glucose, O-4,6-dideoxy-4-(((1S-(1-alpha,4-alpha,5-beta,6-alpha ))-4,5,6-trihydroxy-3- (hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-gluc opyranosyl-(1-4)-O-al pha- D-glucopyranosyl-(1-4)-
CAS REGISTRY NUMBER :
56180-94-0
LAST UPDATED :
199704
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C25-H43-N-O18
MOLECULAR WEIGHT :
645.69

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
360 mg/kg/60D-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes Liver - liver function tests impaired
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 124,931,1996
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
24 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,2,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,2,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,2,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
24 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,2,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
12 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,2,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
72800 mg/kg/13W-I
TOXIC EFFECTS :
Gastrointestinal - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,4341,1989
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases 24/25
RIDADR NONH for all modes of transport
RTECS LZ7153000
HS Code 29400090

~60%

56180-94-0 structure

56180-94-0

Literature: Shibata, Yasushi; Ogawa, Seiichiro Carbohydrate Research, 1989 , vol. 189, p. 309 - 322

~%

56180-94-0 structure

56180-94-0

Literature: Journal of the Chemical Society, Chemical Communications, , p. 605 - 606
Precursor  1

DownStream  0

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