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2D Structure
Also known as: 8013-17-0, Invert sugar, Hs 500, 2,3,4,5,6-pentahydroxyhexanal;1,3,4,5,6-pentahydroxyhexan-2-one, Sugar,invert, Schembl20361633
Molecular Formula
C12H24O12
Molecular Weight
360.31  g/mol
InChI Key
PJVXUVWGSCCGHT-UHFFFAOYSA-N

Invert sugar is obtained from sugar cane when this is treated with dilute acid or with the invertase enzyme. It is formed by an equal amount of glucose and fructose. It differentiates from sugar cane in the rotation of the polarized light, which in the case of invert sugar it is to the left (levorotatory). Invert sugar is FDA approved since 1988 as a safe substance (GRAS).
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,3,4,5,6-pentahydroxyhexanal;1,3,4,5,6-pentahydroxyhexan-2-one
2.1.2 InChI
InChI=1S/2C6H12O6/c2*7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2;1,3-6,8-12H,2H2
2.1.3 InChI Key
PJVXUVWGSCCGHT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(C(C(C(C(C=O)O)O)O)O)O.C(C(C(C(C(=O)CO)O)O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Invert Sugar

2.2.2 Depositor-Supplied Synonyms

1. 8013-17-0

2. Invert Sugar

3. Hs 500

4. 2,3,4,5,6-pentahydroxyhexanal;1,3,4,5,6-pentahydroxyhexan-2-one

5. Sugar,invert

6. Schembl20361633

7. Mfcd00148911

8. 1,3,4,5,6-pentahydroxyhexan-2-one; 2,3,4,5,6-pentahydroxyhexanal

9. 2,3,4,5,6-pentahydroxyhexanal Compound With 1,3,4,5,6-pentahydroxyhexan-2-one (1:1)

2.3 Create Date
2007-12-05
3 Chemical and Physical Properties
Molecular Weight 360.31 g/mol
Molecular Formula C12H24O12
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count12
Rotatable Bond Count10
Exact Mass360.12677620 g/mol
Monoisotopic Mass360.12677620 g/mol
Topological Polar Surface Area236 Ų
Heavy Atom Count24
Formal Charge0
Complexity285
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count7
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Cariogenic Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


SOLN CONTAINING 25% TO 50% DEXTROSE ARE USED IN PARENTERAL HYPERALIMENTATION. THESE MAY BE ADMIN SLOWLY TO PROVIDE AS MUCH AS 3,000-4,000 CALORIES DAILY, & MUST BE GIVEN VIA THE SUPERIOR VENA CAVA OR OTHER EQUALLY LARGE VEIN. /DEXTROSE/

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 181


SOLN CONTAINING 50% TO 75% DEXTROSE DECR THE FREQUENCY OF DIALYSIS IN PATIENTS WITH RENAL FAILURE. /DEXTROSE/

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 181


4.2 Drug Warning

IF THE INDIVIDUAL PATIENT'S CAPACITY TO UTILIZE DEXTROSE IS EXCEEDED, GLYCOSURIA & DIURESIS WILL OCCUR. /DEXTROSE/

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 181


10% SOLN OF INVERT SUGAR BUFFERED TO PH 6.8 WAS FOUND TO CAUSE SIGNIFICANTLY LOWER INCIDENCE OF THROMBOPHLEBITIS THAN SOLN OF SAME STRENGTH WITH PH BETWEEN 3.5 AND 5.4 FOLLOWING INTRAVENOUS INJECTION OF 500 ML QUANTITIES IN 76 PATIENTS.

Blacow, N. W. (ed.). Martindale: The Extra Pharmacopoeia. 26th ed. London: The Pharmaceutical Press, 1972., p. 81


DEXTROSE INJECTION SHOULD NOT BE USED AS A DILUENT FOR BLOOD BECAUSE IT CAUSES CLUMPING OF RED BLOOD CELLS &, POSSIBLY, HEMOLYSIS. THIS CAN BE AVOIDED BY USING 5% DEXTROSE IN 0.2% OR 0.11% SODIUM CHLORIDE INJECTION. /DEXTROSE/

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 181


SUBCUTANEOUS /ADMIN OF INVERT SUGAR/: GENERALLY DEEMED INADVISABLE.

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 181


For more Drug Warnings (Complete) data for INVERT SUGAR (7 total), please visit the HSDB record page.


4.3 Drug Indication

Invert sugar presents a large variety of uses. It can be used therapeutically for parenteral hyperalimentation or to be used as an excipient with a known effect. Invert sugar is also approved for its use in food products as a humectant, crystallization modifier, and liquid and nutritive sweetener.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Intravenous administration of invert sugar has been proven to be favorable. These reports indicate a temporary rise, within physiological levels, of lactate, pyruvate, and insulin in the blood plasma whereas the level of free fatty acids was declined.


5.2 MeSH Pharmacological Classification

Cariogenic Agents

Substances that promote DENTAL CARIES. (See all compounds classified as Cariogenic Agents.)


Sweetening Agents

Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) (See all compounds classified as Sweetening Agents.)


5.3 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

C05B - Antivaricose therapy

C05BB - Sclerosing agents for local injection

C05BB03 - Invert sugar


5.4 Absorption, Distribution and Excretion

Absorption

It has been reported that administration of 10-15% of intravenous invert sugar solution is rapidly absorbed in the intestine and distributed in blood without exceeding the renal threshold. The absorption of invert sugar happens mainly as monosaccharides. Glucose is absorbed into the portal vein by the transporter GLUT2 while fructose is absorbed by the transporter GLUT5.


Route of Elimination

Reports have indicated that after intravenous administration of invert sugar present a reduced content or carbohydrates in urine when compared to the intravenous administration of glucose. This response indicates a reduced diuresis of invert sugar. It has also been reported a reduced diuresis in the presence of invert diuresis.


LESS THAN 2% OF SUGAR IS EXCRETED IN URINE WHEN 1 L OF 10% INVERT SUGAR SOLN IS INFUSED IN 1 HR. WHEN GIVEN OVER A LONGER PERIOD OF TIME INVERT SUGAR IS COMPLETELY UTILIZED AND NONE IS EXCRETED IN URINE.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 40:20


5.5 Metabolism/Metabolites

The metabolism of invert sugar and other fructose-glucose sweeteners is not meaningfully different. Once absorbed, the fructose monosaccharides are taken up by the liver and bypass a key step regulatory step in glycolysis. Both of the monosaccharides first step metabolism is marked by its phosphorylation to glucose-6-phosphate by glucokinase or fructose-1-phosphate by fructokinase. After this step, the glycolysis continues its pathway until the obtention of pyruvic acid. The metabolism of fructose is more rapid than the one of glucose and thus, it is possible to administer at the same speed than a glucose dose correspondent to 55% of the invert sugar dose.


5.6 Biological Half-Life

The glucose half-life following intravenous administration of invert sugar is of approximately 30 min. In the same report, the half-life of fructose after the intravenous administration is reported to be 16 min.