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Chemistry

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Also known as: D-arabino-hex-2-ulo-pyranose, D-fru, D-fructopyranose, D-fructopyranoside, Fru, Fructopyranose
Molecular Formula
C6H12O6
Molecular Weight
180.16  g/mol
InChI Key
LKDRXBCSQODPBY-VRPWFDPXSA-N

D-Fructose API
Fructose is a metabolite found in the aging mouse brain.
1 2D Structure

D-Fructose API

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
2.1.2 InChI
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4-,5+,6?/m1/s1
2.1.3 InChI Key
LKDRXBCSQODPBY-VRPWFDPXSA-N
2.1.4 Canonical SMILES
C1C(C(C(C(O1)(CO)O)O)O)O
2.1.5 Isomeric SMILES
C1[C@H]([C@H]([C@@H](C(O1)(CO)O)O)O)O
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. D-arabino-hex-2-ulo-pyranose

2. D-fru

3. D-fructopyranose

4. D-fructopyranoside

5. Fru

6. Fructopyranose

7. Fructopyranoside

8. Fructose

9. Chebi:37714

10. 6347-01-9

11. [14c]-fructose

12. Schembl239448

13. Chembl2325229

14. C6h12o6

15. Akos004910390

16. F0317

17. C05003

18. Q27117234

19. Wurcs=2.0/1,1,0/[ha122h-2x_2-6]/1/

20. Eb37038e-44a6-4af7-b0d8-47a315ad2f74

21. (3s,4r,5r)-2-(hydroxymethyl)tetrahydro-2h-pyran-2,3,4,5-tetraol

2.3 Create Date
2005-07-19
3 Chemical and Physical Properties
Molecular Weight 180.16 g/mol
Molecular Formula C6H12O6
XLogP3-2.8
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass180.06338810 g/mol
Monoisotopic Mass180.06338810 g/mol
Topological Polar Surface Area110 Ų
Heavy Atom Count12
Formal Charge0
Complexity162
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

...IT IS UTILIZED BY DIABETIC PATIENTS WITH KETOACIDOSIS...MAY BE USEFUL IN EARLY MANAGEMENT OF THIS COMPLICATION OF DIABETES MELLITUS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 769


MEDICATION (VET): AS A SUBSTITUTE FOR GLUCOSE IN PARENTERAL FLUIDS SINCE IT DOES NOT EXCEED RENAL THRESHOLD AS READILY. THUS, 10% SOLN CAN BE USED INSTEAD OF 5% GLUCOSE PROVIDING MORE TOTAL CALORIES PER ML, & THIS ACCOUNTS FOR ITS USE IN ACETONEMIA THERAPY IN ADULT CATTLE.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 229


FRUCTOSE SOLN, LIKE THOSE OF DEXTROSE, ARE EMPLOYED TO REPLACE OR SUPPLEMENT ORAL CONSUMPTION OF FOOD OR WATER IN ORDER TO PROVIDE CALORIES REQUIRED FOR METABOLIC NEEDS, TO SUPPLY BODY WATER, TO SPARE BODY PROTEINS, TO LOWER PRODN OF EXCESS KETONES BY LIVER, & TO SPARE LOSS OF ELECTROLYTES.

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


DENTAL ASPECTS OF CONSUMPTION OF FRUCTOSE DIETS RESULTED IN REDUCTION OF INCIDENCE OF DENTAL CARIES BY 30%.

MAKINEN KK; INT DENT J 26(1) 14 (1976)


For more Therapeutic Uses (Complete) data for FRUCTOSE (6 total), please visit the HSDB record page.


4.2 Drug Warning

SUBCUTANEOUS ROUTE IS NOT RECOMMENDED, BECAUSE SUGARS GIVEN SC CAUSE ELECTROLYTE DISTORTIONS, WHICH OCCASIONALLY MAY BE SEVERE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 964


FRUCTOSE IS NONTOXIC BUT SOLN SHOULD BE ADMIN SLOWLY. IT DECOMPOSES IN ALKALINE SOLN & THUS SUBSTANCES WHICH WOULD RAISE PH ABOVE 7 SHOULD NOT BE ADDED. CALCIUM & BARIUM FORM INSOL COMPLEXES WITH FRUCTOSE WHEN PH EXCEEDS 7 & ARE THUS INCOMPATIBLE. CLOUDY SOLN OF FRUCTOSE SHOULD NOT BE USED.

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


5 Pharmacology and Biochemistry
5.1 ATC Code

V - Various

V06 - General nutrients

V06D - Other nutrients

V06DC - Carbohydrates

V06DC02 - Fructose


5.2 Absorption, Distribution and Excretion

TWICE THE CONCN OF FRUCTOSE CAN BE INFUSED AT THE SAME RATE AS DEXTROSE WITH BETTER RETENTION AND LESS DISTURBANCE OF FLUID BALANCE.

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


...ADVANTAGES OF FRUCTOSE IS ITS RAPID REMOVAL FROM EXTRACELLULAR SPACE, & THEREFORE, URINARY EXCRETION IS MINIMIZED.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 769


5.3 Metabolism/Metabolites

IN ABSENCE OF GLUCOSE, FRUCTOSE IS PHOSPHORYLATED PERIPHERALLY BY HEXOKINASE TO FRUCTOSE-6-PHOSPHATE, &, ON ACCOUNT OF HIGH KM VALUE FOR FRUCTOSE & LOW KM VALUE FOR GLUCOSE, LATTER IS PREFERENTIALLY PHOSPHORYLATED BY THIS ENZYME IN PERIPHERAL TISSUES.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 171


ORAL FRUCTOSE IS OFTEN CONVERTED TO GLUCOSE IN INTESTINAL MUCOSA OF A NUMBER OF SPECIES, SUCH AS GUINEA PIG, HAMSTER, & DOG. NEWBORN PIGS & YOUNG CALVES UP TO 1 MO OF AGE CANNOT UTILIZE IT. SPECIES...WITH LOW GLUCOSE-6-PHOSPHATE DEHYDROGENASE & RELATED ENZYME DEFICIENCIES MAY HAVE DIFFICULTY IN METABOLIZING IT.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 229


FRUCTOSE IS MORE RAPIDLY METABOLIZED & MORE QUICKLY CONVERTED TO GLYCOGEN THAN IS DEXTROSE, & PRESENCE OF INSULIN IS NOT NECESSARY FOR THIS REACTION TO TAKE PLACE. WHEN...INJECTED LOWER LEVELS OF BLOOD SUGAR & LESS SPILLAGE RESULT THAN WHEN SIMILAR AMT OF DEXTROSE ARE GIVEN @ SAME RATE.

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


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