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Details

Stereochemistry ACHIRAL
Molecular Formula C6H12O7.C6H11O6.C3H5ClO.Fe
Molecular Weight 523.672
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUSOFERRON

SMILES

[Fe+3].ClCC1CO1.OC[C@@H](O)[C@@H](O)[C@H]([O-])[C@@H]([O-])C[O-].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O

InChI

InChIKey=VGDATRQLXLLOSX-MFOKLRKYSA-N
InChI=1S/C6H12O7.C6H11O6.C3H5ClO.Fe/c7-1-2(8)3(9)4(10)5(11)6(12)13;7-1-3(9)5(11)6(12)4(10)2-8;4-1-3-2-5-3;/h2-5,7-11H,1H2,(H,12,13);3-7,9,11H,1-2H2;3H,1-2H2;/q;-3;;+3/t2-,3-,4+,5-;3-,4+,5-,6-;;/m11../s1

HIDE SMILES / InChI
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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Osmitrol

Approved Use

Osmitrol 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 Date

1964
Primary
Osmitrol

Approved Use

Osmitrol 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 Date

1964
Primary
Osmitrol

Approved Use

Osmitrol 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 Date

1964
Diagnostic
ARIDOL

Approved Use

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.

Launch Date

2010
Palliative
Bronchitol

Approved Use

Bronchitol 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 Date

2012
Primary
SORBITOL 3.3% IN PLASTIC CONTAINER

Approved Use

Renagel 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 Date

1978
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of sodium polystyrene sulfonate on lithium bioavailability.
1992 Nov
Detection and characterization of verotoxin-producing strains among sorbitol non-fermenting Escherichia coli.
2001 Jul-Sep
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
Membrane-bound D-sorbitol dehydrogenase of Gluconobacter suboxydans IFO 3255--enzymatic and genetic characterization.
2003 Apr 11
New quinoproteins in oxidative fermentation.
2003 Apr 11
[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
Attenuated total reflectance Fourier transform mid-infrared spectroscopic quantification of sorbitol and sorbose during a Gluconobacter biotransformation process.
2003 Feb
New developments in oxidative fermentation.
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
Genetic relationships among avian isolates classified as Pasteurella haemolytica, 'Actinobacillus salpingitidis' or Pasteurella anatis with proposal of Gallibacterium anatis gen. nov., comb. nov. and description of additional genomospecies within Gallibacterium gen. nov.
2003 Jan
Effect of glucose on assimilatory sulphate reduction in Arabidopsis thaliana roots.
2003 Jul
[Evaluating liver functional reserve by combining D-sorbitol with indocyanine green measurement].
2003 Jun
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
Evaluation of the site(s) of glycation in human proinsulin by ion-trap LCQ electrospray ionization mass spectrometry.
2003 May 15
Nucleation of one polymorph by another.
2003 May 28
D-xylose metabolism in Hypocrea jecorina: loss of the xylitol dehydrogenase step can be partially compensated for by lad1-encoded L-arabinitol-4-dehydrogenase.
2003 Oct
In vitro cytotoxic effects of stabilizing sugars within human intravenous immunoglobulin preparations against the human macrophage THP-1 cell-line.
2003 Oct
Home-prepared hamburger and sporadic hemolytic uremic syndrome, Argentina.
2003 Sep
Evaluation of liver functional reserve by combining D-sorbitol clearance rate and CT measured liver volume.
2003 Sep
The heat shock protein 90 of Plasmodium falciparum and antimalarial activity of its inhibitor, geldanamycin.
2003 Sep 15
[Comparative analysis of dependence of saliva sorbitol and fructosamine levels on blood glucose level in patients with diabetes].
2004
Autodisplay of active sorbitol dehydrogenase (SDH) yields a whole cell biocatalyst for the synthesis of rare sugars.
2004 Apr 2
Aeromonas spp. and infectious diarrhea, Hong Kong.
2004 Aug
Growth and characterisation of primary bovine colon epithelial cells in vitro.
2004 Dec
Effect of physical exercise on human preference for solutions of various sweet substances.
2004 Dec
Polyol pathway along the bovine epididymis.
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
Functional hepatic flow in patients with liver cirrhosis.
2004 Mar 15
The metabolic role and evolution of L-arabinitol 4-dehydrogenase of Hypocrea jecorina.
2004 May
[Sorbitol].
2004 Nov
Mycobacterium cosmeticum sp. nov., a novel rapidly growing species isolated from a cosmetic infection and from a nail salon.
2004 Nov
Mild detergent treatment of Candida tropicalis reveals a NADPH-dependent reductase in the crude membrane fraction, which enables the production of pure bicyclic exo-alcohol.
2004 Nov
Anaphylaxis to excipient mannitol: evidence for an immunoglobulin E-mediated mechanism.
2004 Oct
C2-symmetric diphosphinite ligands derived from carbohydrates. The strong influence of remote stereocenters on asymmetric rhodium-catalyzed hydrogenation.
2004 Oct 29
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
A sensitive assay of red blood cell sorbitol level by high performance liquid chromatography: potential for diagnostic evaluation of diabetes.
2005 Apr
Water T2 relaxation in sugar solutions.
2005 Apr 11
Oral contrast agents for small bowel distension in MRI: influence of the osmolarity for small bowel distention.
2005 Jul
Microbial production of L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone by Ketogulonicigenium vulgare DSM 4025.
2005 Mar
Patents

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
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)
Name Type Language
GLUSOFERRON
INN  
INN  
Official Name English
glusoferron [INN]
Common Name English
D-GLUCONIC ACID, POLYMER WITH (CHLOROMETHYL)OXIRANE AND D-GLUCITOL, IRON(3+) SALT
Common Name English
FERASTRAL
Brand Name English
A-2152
Code English
Code System Code Type Description
FDA UNII
R79WUI68IB
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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CAS
56959-18-3
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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NCI_THESAURUS
C170030
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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INN
4234
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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ChEMBL
CHEMBL2108434
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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SMS_ID
300000034216
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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PUBCHEM
171553
Created by admin on Sat Dec 16 08:25:56 GMT 2023 , Edited by admin on Sat Dec 16 08:25:56 GMT 2023
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