Sorbitol

Identification

Name
Sorbitol
Accession Number
DB01638  (EXPT02939, DB09391)
Type
Small Molecule
Groups
Approved
Description

A polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures.

Structure
Thumb
Synonyms
  • (−)-sorbitol
  • D-(−)-sorbitol
  • D-glucitol
  • D-Sorbit
  • D-Sorbitol
  • G-ol
  • L-Gulitol
External IDs
7B5697N / E 420 / E-420 / E420 / FEMA NO. 3029 / NSC-25944
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SorbitolIrrigant3.3 g/100mLIrrigationB. Braun Medical Inc.1978-02-16Not applicableUs
SorbitolIrrigant30 g/1000mLIrrigationBaxter Laboratories1980-05-30Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SorbitolSolution1 g/mLRectalH&H Laboratories, Inc.2013-06-10Not applicableUs
SorbitolSolution258.2 g/474mLOralGeritrex Llc2012-07-17Not applicableUs
SorbitolSolution13.5 g/15mLRectalGericare Pharmaceuticals2000-01-01Not applicableUs
Sorbitol Rougier Pws 5gmPowder, for solution5 gOralRougier Pharma Division Of Ratiopharm Inc1975-12-312001-09-05Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Char-flo With Sorbitol - SusSorbitol (400 mg) + Activated charcoal (208 mg)SuspensionOralBallard Medical Products1997-08-202004-08-04Canada
Cystosol W 3% HexitolsSorbitol (2.5 g) + Mannitol (500 mg)LiquidIrrigationBaxter Laboratories1989-12-31Not applicableCanada
Microlax Micro EnemaSorbitol (625 mg) + Sodium Citrate (90 mg) + Sodium lauryl sulfoacetate (9 mg)Enema; LiquidRectalMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1995-12-31Not applicableCanada
Microlax Micro-enemaSorbitol (625 g) + Sodium Citrate (90 g) + Sodium lauryl sulfoacetate (9 g)LiquidRectalKabi Pharmacia Canada Inc.1993-12-311996-09-10Canada
Salivart AerSorbitol (3 %) + Calcium Chloride (.015 %) + Carboxymethylcellulose sodium (1 %) + Dipotassium phosphate (.034 %) + Magnesium chloride (.005 %) + Potassium Chloride (.12 %) + Sodium Chloride (.084 %)AerosolOralAll Star Sales and Service Ltd.1990-12-311997-11-10Canada
Sorbitol Mannitol IrrigationSorbitol (27 mg) + Mannitol (5.4 mg)SolutionIrrigationIcu Medical Canada Inc1980-12-31Not applicableCanada
Sorbitol-MannitolSorbitol (2.7 g/100mL) + Mannitol (.54 g/100mL)IrrigantUrethralHospira, Inc.1980-02-22Not applicableUs
Categories
UNII
506T60A25R
CAS number
50-70-4
Weight
Average: 182.1718
Monoisotopic: 182.07903818
Chemical Formula
C6H14O6
InChI Key
FBPFZTCFMRRESA-JGWLITMVSA-N
InChI
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
IUPAC Name
(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
SMILES

Pharmacology

Indication

Used as a non-stimulant laxative via an oral suspension or enema.

Structured Indications
Pharmacodynamics
Not Available
Mechanism of action

Sorbitol exerts its laxative effect by drawing water into the large intestine, thereby stimulating bowel movements.

TargetActionsOrganism
UXylose isomeraseNot AvailableStreptomyces rubiginosus
UXylose isomeraseNot AvailableActinoplanes missouriensis (strain ATCC 14538 / DSM 43046 / CBS 188.64 / JCM 3121 / NCIMB 12654 / NBRC 102363 / 431)
UXylose isomeraseNot AvailableArthrobacter sp. (strain NRRL B3728)
UMalate synthase GNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Sorbitol will either be excreted in the urine by the kidneys, or metabolized to carbon dioxide and dextrose.

Half life
Not Available
Clearance
Not Available
Toxicity

Acute oral toxicity (LD50): 15900 mg/kg [Rat].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Fructose intolerance, hereditaryDisease
GalactosemiaDisease
FructosuriaDisease
Galactose MetabolismMetabolic
Fructose and Mannose DegradationMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Gerhard Darsow, "Process for the preparation of epimer-free sugar alcohols from the group consisting of xylitol, sorbitol (D-glucitol), 4-O-.beta.-D-galactopyranosyl-D-glucitol and 4-O-.alpha.-D-glucopyranosyl-D-sorbitol." U.S. Patent US5162517, issued August, 1985.

US5162517
General References
Not Available
External Links
Human Metabolome Database
HMDB00247
KEGG Drug
D00096
KEGG Compound
C00794
PubChem Compound
5780
PubChem Substance
46507030
ChemSpider
5576
ChEBI
17924
ChEMBL
CHEMBL1682
PharmGKB
PA451455
HET
SOR
Wikipedia
Sorbitol
ATC Codes
A06AD18 — SorbitolA06AG07 — SorbitolV04CC01 — SorbitolB05CX02 — Sorbitol
AHFS Codes
  • 56:12.00 — Cathartics and Laxatives
PDB Entries
1d8c / 1fqa / 1fqb / 1xih / 2dxr / 2vft / 2xin / 3brf / 3xim / 4dvo
show 6 more
MSDS
Download (47.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentPain, Acute1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentGeneral Surgery / Ileus / Occasional Constipation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionOral
LiquidIrrigation
Enema; liquidRectal
LiquidRectal
AerosolOral
IrrigantIrrigation3.3 g/100mL
IrrigantIrrigation30 g/1000mL
SolutionOral258.2 g/474mL
SolutionRectal1 g/mL
SolutionRectal13.5 g/15mL
SolutionIrrigation
Powder, for solutionOral5 g
IrrigantUrethral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)111http://pubchem.ncbi.nlm.nih.gov/compound/5780?from=summary
water solubility2.75E+006 mg/L (at 30 °C)MULLIN,JW (1972)
logP-2.20SANGSTER (1994)
logS1.09ADME Research, USCD
pKa13.6BENSON,FR (1978)
Predicted Properties
PropertyValueSource
Water Solubility229.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m3·mol-1ChemAxon
Polarizability17.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6525
Blood Brain Barrier-0.5997
Caco-2 permeable-0.8958
P-glycoprotein substrateNon-substrate0.662
P-glycoprotein inhibitor INon-inhibitor0.9535
P-glycoprotein inhibitor IINon-inhibitor0.9551
Renal organic cation transporterNon-inhibitor0.9252
CYP450 2C9 substrateNon-substrate0.8706
CYP450 2D6 substrateNon-substrate0.878
CYP450 3A4 substrateNon-substrate0.7431
CYP450 1A2 substrateNon-inhibitor0.824
CYP450 2C9 inhibitorNon-inhibitor0.9419
CYP450 2D6 inhibitorNon-inhibitor0.9412
CYP450 2C19 inhibitorNon-inhibitor0.9232
CYP450 3A4 inhibitorNon-inhibitor0.9402
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.958
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7823
BiodegradationReady biodegradable0.8595
Rat acute toxicity1.1260 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9709
hERG inhibition (predictor II)Non-inhibitor0.9329
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0ldj-0941000000-19d96a9ba7ba0c482c83
GC-MS Spectrum - GC-MS (6 TMS)GC-MSsplash10-014i-1973000000-d907b75f68a7927501a7
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ldj-0941000000-19d96a9ba7ba0c482c83
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1973000000-d907b75f68a7927501a7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ktb-0931000000-4ffadb4b25e8e2510d93
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-017j-8900000000-700285f86eac0a3501d1
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-066r-9000000000-84676b839b145250d67d
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-052f-9000000000-dce72cab270c488d65da
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0ik9-2900000000-26a16e983791be7818f2
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0ik9-2900000000-6513771e890cbff9c402
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0900000000-58e6917626e28d1830a2
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0900000000-83169b2192f847cc0636
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0900000000-4cd721d87e359527adf3
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0900000000-b44f68c64bc74e79e9fc
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0900000000-bbb5e957a9e67ddc411e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-772c3052966c05f29842
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-d1fbea514e7f1c1628f2
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0790000000-b5b098cd5b4b4ec10821
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0690000000-41d4e48d49836c63485c
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Sugar alcohols
Alternative Parents
Monosaccharides / Secondary alcohols / Polyols / Primary alcohols / Hydrocarbon derivatives
Substituents
Sugar alcohol / Monosaccharide / Secondary alcohol / Polyol / Hydrocarbon derivative / Primary alcohol / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
glucitol (CHEBI:17924)

Targets

Kind
Protein
Organism
Streptomyces rubiginosus
Pharmacological action
Unknown
General Function
Xylose isomerase activity
Specific Function
Involved in D-xylose catabolism.
Gene Name
xylA
Uniprot ID
P24300
Uniprot Name
Xylose isomerase
Molecular Weight
43226.915 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Actinoplanes missouriensis (strain ATCC 14538 / DSM 43046 / CBS 188.64 / JCM 3121 / NCIMB 12654 / NBRC 102363 / 431)
Pharmacological action
Unknown
General Function
Xylose isomerase activity
Specific Function
Not Available
Gene Name
xylA
Uniprot ID
P12851
Uniprot Name
Xylose isomerase
Molecular Weight
43498.425 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Arthrobacter sp. (strain NRRL B3728)
Pharmacological action
Unknown
General Function
Xylose isomerase activity
Specific Function
Not Available
Gene Name
xylA
Uniprot ID
P12070
Uniprot Name
Xylose isomerase
Molecular Weight
43291.15 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in the glycolate utilization. Catalyzes the condensation and subsequent hydrolysis of acetyl-coenzyme A (acetyl-CoA) and glyoxylate to form malate and CoA.
Gene Name
glcB
Uniprot ID
P37330
Uniprot Name
Malate synthase G
Molecular Weight
80487.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2017 21:49