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CAS No.: | 56180-94-0 |
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Name: | Acarbose |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C25H43NO18 |
Molecular Weight: | 645.612 |
Synonyms: | D-Glucose,O-4,6-dideoxy-4-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-(1?;4)-, [1S-(1a,4a,5b,6a)]-;Ascarbose;BAY-g 5421;Glucobay;Prandase;Precose;Acarbose EP5; |
EINECS: | 260-030-7 |
Density: | 1.74 g/cm3 |
Melting Point: | 165-170 °C |
Boiling Point: | 971.6 °C at 760 mmHg |
Flash Point: | 541.4 °C |
Solubility: | very soluble in water, soluble in methanol, practically insoluble in methylene chloride |
Appearance: | Off-white solid |
Safety: | 24/25 |
PSA: | 321.17000 |
LogP: | -8.17360 |
The Acarbose, with the CAS registry number 56180-94-0, is also known as Acarbosum. It belongs to the product categories of Sugars, Carbohydrates & Glucosides; Intermediates & Fine Chemicals; Oligosaccharides; Pharmaceuticals; API's. Its EINECS registry number is 260-030-7. This chemical's molecular formula is C25H43NO18 and molecular weight is 645.605. Its IUPAC name is called (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.
Physical properties of Acarbose: (1)ACD/LogP: -4.17; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -4.61; (4)ACD/LogD (pH 7.4): -4.17; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 19; (10)#H bond donors: 14; (11)#Freely Rotating Bonds: 22; (12)Index of Refraction: 1.689; (13)Molar Refractivity: 141.21 cm3; (14)Molar Volume: 369.7 cm3; (15)Surface Tension: 114.5 dyne/cm; (16)Density: 1.74 g/cm3; (17)Flash Point: 541.4 °C; (18)Enthalpy of Vaporization: 160.48 kJ/mol; (19)Boiling Point: 971.6 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
Acarbose is an anti-diabetic drug used to treat type 2 diabetes mellitus and, in some countries, prediabetes. It is sold in Europe under the brand name Glucobay (Bayer AG), in North America as Precose (Bayer Pharmaceuticals), and in Canada as Prandase (Bayer AG). It is an inhibitor of alpha glucosidase, an enteric enzyme that releases glucose from larger carbohydrates. Hepatitis has been reported with acarbose use. It usually goes away when the medicine is stopped.
You can still convert the following datas into molecular structure:
(1)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
(2)InChI: InChI=1/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
(3)InChIKey: XUFXOAAUWZOOIT-SXARVLRPBZ
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | oral | 10gm/kg (10000mg/kg) | Pharmaceutical Chemistry Journal Vol. 23, Pg. 82, 1989. | |
man | TDLo | oral | 56mg/kg/13D-I (56mg/kg) | BLOOD: EOSINOPHILIA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Lancet. Vol. 354, Pg. 396, 1999. |
mouse | LD50 | intravenous | 12gm/kg (12000mg/kg) | Drugs in Japan Vol. -, Pg. 2, 1995. | |
mouse | LD50 | oral | 24gm/kg (24000mg/kg) | Drugs in Japan Vol. -, Pg. 2, 1995. | |
rat | LD50 | intravenous | 6gm/kg (6000mg/kg) | Drugs in Japan Vol. -, Pg. 2, 1995. | |
rat | LD50 | oral | 24gm/kg (24000mg/kg) | Drugs in Japan Vol. -, Pg. 2, 1995. | |
rat | LD50 | subcutaneous | 12gm/kg (12000mg/kg) | Drugs in Japan Vol. -, Pg. 2, 1995. | |
women | TDLo | oral | 360mg/kg/60D- (360mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: LIVER FUNCTION TESTS IMPAIRED | Annals of Internal Medicine. Vol. 124, Pg. 931, 1996. |
women | TDLo | oral | 378mg/kg/9W-I (378mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: LIVER FUNCTION TESTS IMPAIRED | Lancet. Vol. 349, Pg. 698, 1997 |