Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H14O6 |
Molecular Weight | 182.1718 |
Optical Activity | ( - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI
InChIKey=FBPFZTCFMRRESA-KVTDHHQDSA-N
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
Molecular Formula | C6H14O6 |
Molecular Weight | 182.1718 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=16cc9d47-5382-4237-ab84-f22c5436fe2ehttps://www.drugbank.ca/drugs/DB00742 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022368Orig1s000LBL.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/013684s091lbl.pdfCurator's Comment: description was created based on several sources, including:
http://www.sailhome.org/Concerns/Vaccines.html
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=16cc9d47-5382-4237-ab84-f22c5436fe2ehttps://www.drugbank.ca/drugs/DB00742 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022368Orig1s000LBL.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/013684s091lbl.pdf
Curator's Comment: description was created based on several sources, including:
http://www.sailhome.org/Concerns/Vaccines.html
Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. Mannitol (marketed under the brand Osmitrol) may also be used for the promotion of diuresis before irreversible renal failure becomes established; the promotion of urinary excretion of toxic substances; as an Antiglaucoma agent; and as a renal function diagnostic aid. Mannitol, the active ingredient in ARIDOL, is indicated for the assessment of bronchial hyperresponsiveness in patients 6 years of age or older who do not have clinically apparent asthma. Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. As a diurectic mannitol induces diuresis because it is not reabsorbed in the renal tubule, thereby increasing the osmolality of the glomerular filtrate, facilitating excretion of water, and inhibiting the renal tubular reabsorption of sodium, chloride, and other solutes. Mannitol promotes the urinary excretion of toxic materials and protects against nephrotoxicity by preventing the concentration of toxic substances in the tubular fluid. As an Antiglaucoma agent mannitol elevates blood plasma osmolarity, resulting in enhanced flow of water from the eye into plasma and a consequent reduction in intraocular pressure. As a renal function diagnostic aid mannitol is freely filtered by the glomeruli with less than 10% tubular reabsorption. Therefore, its urinary excretion rate may serve as a measurement of glomerular filtration rate (GFR).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=26035307https://www.anaesthesiamcq.com/FluidBook/fl8_5.php
Curator's Comment: Mannitol does not cross the blood-brain barrier so an elevated plasma osmolality due to an infusion of hypertonic mannitol is effective in removing fluid from the brain.
Originator
Sources: Alternative Sweeteners, Third Edition, Revised and Expanded. Ed. Lyn O'Brien-Nabors. CRC Press, 2001 . - pp. 572https://books.google.ru/books?id=_F1YSezlIzwC&pg=PA268&lpg=PA268&dq=mannitol retrieved from Carbohydrates, p.268
Curator's Comment: The first sugar alcohol isolated was mannitol from manna of ash (Fraxinus sp.) by Proust in 1806
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Osmitrol Approved UseOsmitrol Injection (Mannitol Injection, USP) is indicated for:
The promotion of diuresis, in the prevention and/or treatment of the oliguric phase of acute renal
failure before irreversible renal failure becomes established;
The reduction of intracranial pressure and treatment of cerebral edema by reducing brain mass;
The reduction of elevated intraocular pressure when the pressure cannot be lowered by other means,
and promoting the urinary excretion of toxic substances. Launch Date1964 |
|||
Primary | Osmitrol Approved UseOsmitrol Injection (Mannitol Injection, USP) is indicated for:
The promotion of diuresis, in the prevention and/or treatment of the oliguric phase of acute renal
failure before irreversible renal failure becomes established;
The reduction of intracranial pressure and treatment of cerebral edema by reducing brain mass;
The reduction of elevated intraocular pressure when the pressure cannot be lowered by other means,
and promoting the urinary excretion of toxic substances. Launch Date1964 |
|||
Primary | Osmitrol Approved UseOsmitrol Injection (Mannitol Injection, USP) is indicated for:
The promotion of diuresis, in the prevention and/or treatment of the oliguric phase of acute renal
failure before irreversible renal failure becomes established;
The reduction of intracranial pressure and treatment of cerebral edema by reducing brain mass;
The reduction of elevated intraocular pressure when the pressure cannot be lowered by other means,
and promoting the urinary excretion of toxic substances. Launch Date1964 |
|||
Diagnostic | ARIDOL Approved UseMannitol, the active ingredient in ARIDOL, is indicated for the assessment of bronchial hyperresponsiveness in patients 6 years of age or older who do not have clinically apparent asthma. Launch Date2010 |
|||
Palliative | Bronchitol Approved UseBronchitol is indicated for the treatment of cystic fibrosis (CF) in adults aged 18 years and above as
an add-on therapy to best standard of care. Launch Date2012 |
|||
Primary | SORBITOL 3.3% IN PLASTIC CONTAINER Approved UseRenagel Capsules are indicated for the reduction of serum phosphorus in patients with end-stage renal disease (ESRD). The safety and efficacy of Renagel Capsules in ESRD patients who are not on hemodialysis have not been studied. In hemodialysis patients, Renagel decreases the incidence of
hypercalcemic episodes relative to patients on calcium acetate treatment. Launch Date1978 |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Quinone reductase inhibitors block SAPK/JNK and NFkappaB pathways and potentiate apoptosis. | 1999 Oct 29 |
|
Sorbitol as a marker for drug-induced decreases of variable duration in liver blood flow in healthy volunteers. | 2000 Dec |
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Intestinal permeability tests in coeliac disease. | 2001 |
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[Production of vitamin C precursor--2-keto-L-gulonic acid from D-sorbitol by mixed culture of microorganisms]. | 2001 Dec |
|
[Intraoperative complications of 697 consecutive operative hysteroscopies]. | 2001 Feb |
|
Intestinal permeability in adult patients with growth hormone deficiency. | 2001 Feb |
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Improving water stress tolerance of the biocontrol yeast Candida sake grown in molasses-based media by physiological manipulation. | 2001 Feb |
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The combined hydrolysis and hydrogenation of inulin catalyzed by bifunctional Ru/C. | 2001 Feb 15 |
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Membrane-bound sugar alcohol dehydrogenase in acetic acid bacteria catalyzes L-ribulose formation and NAD-dependent ribitol dehydrogenase is independent of the oxidative fermentation. | 2001 Jan |
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Gluconobacter oxydans: its biotechnological applications. | 2001 Jul |
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Routes for fructose utilization by Escherichia coli. | 2001 Jul |
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Detection and characterization of verotoxin-producing strains among sorbitol non-fermenting Escherichia coli. | 2001 Jul-Sep |
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Cytochrome c release occurs via Ca2+-dependent and Ca2+-independent mechanisms that are regulated by Bax. | 2001 Jun 1 |
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Melatonin counteracts potentiation by lysophosphatidylcholine of serotonin-induced vasoconstriction in human umbilical artery: relation to calcium influx. | 2001 Mar |
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Roles of glucitol in the GutR-mediated transcription activation process in Bacillus subtilis: tight binding of GutR to tis binding site. | 2001 Mar 30 |
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Design and validation of an annular shear cell for pharmaceutical powder testing. | 2001 May |
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Determination of D-sorbitol in human erythrocytes by an enzymatic fluorometric method with an improved deproteinization procedure. | 2001 Nov |
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The solvent-free thermal dehydration of hexitols on zeolites. | 2002 Aug 16 |
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Effect of replacing the general energy-coupling proteins of the PEP:sugar phosphotransferase system of Salmonella typhimurium with their fructose-inducible counterparts on utilization of the PTS sugar glucitol. | 2002 Dec |
|
Molecular cloning and functional expression of D-sorbitol dehydrogenase from Gluconobacter suboxydans IF03255, which requires pyrroloquinoline quinone and hydrophobic protein SldB for activity development in E. coli. | 2002 Feb |
|
Purification and properties of membrane-bound D-sorbitol dehydrogenase from Gluconobacter suboxydans IFO 3255. | 2002 Jan |
|
Main polyol dehydrogenase of Gluconobacter suboxydans IFO 3255, membrane-bound D-sorbitol dehydrogenase, that needs product of upstream gene, sldB, for activity. | 2002 Nov |
|
Salt-promoted protein folding, preferential binding, or electrostatic screening? | 2002 Nov 1 |
|
Staphylococcus succinus subsp. casei subsp. nov., a dominant isolate from a surface ripened cheese. | 2002 Oct |
|
Application of NAD-dependent polyol dehydrogenases for enzymatic mannitol/sorbitol production with coenzyme regeneration. | 2003 |
|
Physiological characterization of osmotolerant yeast Pichia sorbitophila and comparison with a putative synonym Pichia farinosa. | 2003 |
|
Role of the different mitogen-activated protein kinase subfamilies in the stimulation of dog and human thyroid epithelial cell proliferation by cyclic adenosine 5'-monophosphate and growth factors. | 2003 Apr |
|
[Spinal anesthesia in a patient with hemiparesis after poliomyelitis]. | 2003 Dec |
|
Elimination of oxidative degradation during the per-O-methylation of carbohydrates. | 2003 Dec 31 |
|
New developments in oxidative fermentation. | 2003 Feb |
|
Demonstration of glycated insulin in human diabetic plasma and decreased biological activity assessed by euglycemic-hyperinsulinemic clamp technique in humans. | 2003 Feb |
|
Crystal structure of Pseudomonas fluorescens mannitol 2-dehydrogenase: evidence for a very divergent long-chain dehydrogenase family. | 2003 Feb 1 |
|
Characterization of recombinant xylitol dehydrogenase from Galactocandida mastotermitis expressed in Escherichia coli. | 2003 Feb 1 |
|
Peracetylated 1,6-dibromo-D-glucitol as efficient precursor of 1,6-diiodo and some mono-, disubstituted and heterocyclic D-glucitol derivatives. | 2003 Jan 20 |
|
[Evaluating liver functional reserve by combining D-sorbitol with indocyanine green measurement]. | 2003 Jun |
|
A new endoscopic ureteral reimplantation for primary vesicoureteral reflux (endoscopic trigonoplasty II). | 2003 Mar |
|
Escherichia albertii sp. nov., a diarrhoeagenic species isolated from stool specimens of Bangladeshi children. | 2003 May |
|
Enterococcus phoeniculicola sp. nov., a novel member of the enterococci isolated from the uropygial gland of the Red-billed Woodhoopoe, Phoeniculus purpureus. | 2003 May |
|
Autodisplay of active sorbitol dehydrogenase (SDH) yields a whole cell biocatalyst for the synthesis of rare sugars. | 2004 Apr 2 |
|
Growth and characterisation of primary bovine colon epithelial cells in vitro. | 2004 Dec |
|
A novel UBA and UBX domain protein that binds polyubiquitin and VCP and is a substrate for SAPKs. | 2004 Dec 1 |
|
Gelation behaviors of schizophyllan-sorbitol aqueous solutions. | 2004 Jan |
|
Exploration of essential gene functions via titratable promoter alleles. | 2004 Jul 9 |
|
[Changes in serum Na+ and blood hemoglobin levels during three types of transurethral procedures for the treatment of benign prostatic hypertrophy]. | 2004 Jun |
|
Johari-Goldstein relaxation and crystallization of sorbitol to ordered and disordered phases. | 2004 Mar 15 |
|
Detection of RNA in purified cytomegalovirus virions. | 2004 Sep 1 |
|
Characterization of the AXDH gene and the encoded xylitol dehydrogenase from the dimorphic yeast Arxula adeninivorans. | 2005 Apr |
|
A potent sorbitol dehydrogenase inhibitor exacerbates sympathetic autonomic neuropathy in rats with streptozotocin-induced diabetes. | 2005 Apr |
|
Water T2 relaxation in sugar solutions. | 2005 Apr 11 |
|
Microbial production of L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone by Ketogulonicigenium vulgare DSM 4025. | 2005 Mar |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: 3% sorbitol solution is used as irrigation solution during urinary tract surgery
https://dailymed.nlm.nih.gov/dailymed/getFile.cfm?setid=5f7be402-f25a-428e-b81f-6a4a00de894c&type=pdf&name=5f7be402-f25a-428e-b81f-6a4a00de894c
120 mL of a 25 to 30% w/v solution (Laxative)
Route of Administration:
Rectal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17200660
Curator's Comment: The effects of allopurinol (10(-6)-10(-5) M), deferoxamine (10(-4) M) and mannitol (10(-4)-5 x 10(-3) M) were tested on the transient contraction induced by nicotine. In conclusion, mannitol (5 x 10(-3) M) significantly reduced contractile response to nicotine on EFS only in high concentration. Whereas in small concentrations mannitol (10(-4) M) statistically did not cause any results. https://www.ncbi.nlm.nih.gov/pubmed/20085573
25 mM sorbitol for 7 days (effect of glucose free medium containing sorbitol on mouse retinal progenitor cells)
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:11:13 GMT 2023
by
admin
on
Fri Dec 15 15:11:13 GMT 2023
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Record UNII |
3OWL53L36A
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
BRONCHITOL (AUTHORIZED: CYSTIC FIBROSIS)
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EU-Orphan Drug |
EU/3/05/325
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WHO-ATC |
R05CB16
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WHO-ATC |
B05BC01
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WHO-ESSENTIAL MEDICINES LIST |
16
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WHO-VATC |
QB05CX04
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NCI_THESAURUS |
C49187
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NDF-RT |
N0000175359
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LOINC |
55941-9
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DSLD |
1364 (Number of products:8)
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NDF-RT |
N0000010288
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WHO-ATC |
A06AD16
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NDF-RT |
N0000175810
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WHO-ATC |
B05CX04
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FDA ORPHAN DRUG |
198704
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WHO-VATC |
QB05BC01
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FDA ORPHAN DRUG |
277009
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WHO-VATC |
QA06AD16
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CODEX ALIMENTARIUS (GSFA) |
INS-421
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JECFA EVALUATION |
INS-421
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WHO-VATC |
QR05CB16
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Code System | Code | Type | Description | ||
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87-78-5
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NON-SPECIFIC STEREOCHEMISTRY | |||
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3OWL53L36A
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PRIMARY | |||
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29864
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200-711-8
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SUB03087MIG
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D008353
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935
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69-65-8
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1375105
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6628
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CHEMBL689
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C625
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DB00742
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3OWL53L36A
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MANNITOL
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6251
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16899
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407017
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MANNITOL
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PRIMARY | Description: A white, crystalline powder; odourless. Solubility: Freely soluble in water; very slightly soluble in ethanol (~750 g/l) TS: practically insoluble in ether R. Category: Diuretic. Storage: Mannitol should be kept in a well-closed container. Additional information: Mannitol has a sweet taste. Definition: Mannitol contains not less than 98.0% and not more than 102.0% of C6H14O6, calculated with reference to the driedsubstance. | ||
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SUB20970
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100000091382
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m7080
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PRIMARY | Merck Index |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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