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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H10O8
Molecular Weight 210.1388
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUCARIC ACID

SMILES

O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O

InChI

InChIKey=DSLZVSRJTYRBFB-LLEIAEIESA-N
InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1

HIDE SMILES / InChI

Molecular Formula C6H10O8
Molecular Weight 210.1388
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Glucaric acid is a non-toxic, naturally occurring compound, which is found in small amounts in plants and mammals, including humans. Salts of glucaric acid have potent antiproliferative properties in vivo. The risk of cancer development can be reduced by ingesting food rich in glucaric acid or self-medication with its salts. Glucaric acid inhibits bacterial beta-glucuronidase, thus increasing the excretion of conjugated xenobiotic compounds and decreasing activity of harmful substances. Inhibition of beta-glucuronidase ultimately results in potentially decreasing the risk of carcinogenesis. Calcium salt of the acid demonstrated anti-cancer activity in patients with breast cancer (phase I clinical trial) and in preclinical models of liver, lung, colon and skin cancers. Calcium-D-glucarate is being marketed as a dietary supplement.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Gut microflora beta-glucuronidase
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of acetaminophen in the human neonate: formation of acetaminophen glucuronide and sulfate in relation to plasma bilirubin concentration and D-glucaric acid excretion.
1975 Jun
Melatonin prevents oxidative stress resulting from iron and erythropoietin administration.
2001 Apr
Efficacy of a mixed amphetamine salts compound in adults with attention-deficit/hyperactivity disorder.
2001 Aug
TEMPO-mediated oxidation of maltodextrins and D-glucose: effect of pH on the selectivity and sequestering ability of the resulting polycarboxylates.
2001 Jan 15
Risk of bacterial infection in patients under intravenous iron therapy: dose versus length of treatment.
2001 Nov
Re: Experience with a large dose (500 mg) of intravenous iron dextran and iron saccharate in peritoneal dialysis patients.
2001 Sep-Oct
Ferric saccharate induces oxygen radical stress and endothelial dysfunction in vivo.
2002 Mar
In vitro-in vivo correlations for drugs eliminated by glucuronidation: investigations with the model substrate zidovudine.
2002 Nov
Induction of protein oxidation by intravenous iron in hemodialysis patients: role of inflammation.
2002 Nov
Tolerance and efficacy of intravenous iron saccharate for iron deficiency anemia in children and adolescents receiving long-term parenteral nutrition.
2002 Oct
Prolonged administration over six hours of large doses of intravenous iron saccharate (500 mg) prevents severe adverse reactions in peritoneal dialysis patients.
2002 Sep-Oct
Detoxifying cancer causing agents to prevent cancer.
2003 Jun
Influence of parenteral iron preparations on non-transferrin bound iron uptake, the iron regulatory protein and the expression of ferritin and the divalent metal transporter DMT-1 in HepG2 human hepatoma cells.
2003 Jun 15
Calcium glucarate prevents tumor formation in mouse skin.
2003 Mar
Assessment of copper status in epileptic patients treated with anticonvulsant drugs by measuring the specific oxidase activity of ceruloplasmin.
2003 Oct
Relationship between PCBs in blood and D-glucaric acid in urine.
2003 Sep 15
Determination of iron sucrose (Venofer) or iron dextran (DexFerrum) removal by hemodialysis: an in-vitro study.
2004 Jan 12
AlIII ion complexes of saccharic acid and mucic acid: a solution and solid-state study.
2004 Mar 5
Carbamazepine regulates intestinal P-glycoprotein and multidrug resistance protein MRP2 and influences disposition of talinolol in humans.
2004 Sep
Possible induction of cholinesterase in epileptic patients treated with anticonvulsant drugs: relationship with lipoprotein levels.
2004 Sep
Parenteral iron therapy in treatment of anemia in end-stage renal disease patients: a comparative study between iron saccharate and gluconate.
2005
[Evaluation of the efficacy of intravenous iron III-hydroxide saccharate for treating adult patients with iron deficiency anemia].
2005 Nov-Dec
Purification and characterization of a beta-glucuronidase present during embryogenesis of the mollusk Pomacea sp.
2005 Oct
[Post-haemodilution anaemia in paediatric cardiac surgery: benefit of intravenous iron therapy].
2005 Oct
Poly(glycoamidoamine)s for gene delivery: stability of polyplexes and efficacy with cardiomyoblast cells.
2006 Jan-Feb
Induction of apoptosis by calcium D-glucarate in 7,12-dimethyl benz [a] anthracene-exposed mouse skin.
2007
Diversity of Shewanella population in fish Sparus aurata harvested in the Aegean Sea.
2007 Sep
[Improvement of urinary d-glucaric acid assay and its application].
2008 Jan
Pregnancy in dialysis patients: a case series.
2008 Jan 20
New insights into the alternative D-glucarate degradation pathway.
2008 Jun 6
[The biological role of D-glucaric acid and its derivatives: potential use in medicine].
2008 Sep 5
Global effect of RpoS on gene expression in pathogenic Escherichia coli O157:H7 strain EDL933.
2009 Aug 3
Characterization of metabolites of sibutramine in primary cultures of rat hepatocytes by liquid chromatography-ion trap mass spectrometry.
2009 Feb
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.
2009 Jan 8
Convenient large-scale synthesis of D-glucaro-1,4:6,3-dilactone.
2009 Nov 6
Micro-PET imaging of beta-glucuronidase activity by the hydrophobic conversion of a glucuronide probe.
2009 Sep
Mild reductions in mitochondrial NAD-dependent isocitrate dehydrogenase activity result in altered nitrate assimilation and pigmentation but do not impact growth.
2010 Jan
Patents

Sample Use Guides

The recommended oral dosage of calcium salt of glucaric acid (calcium-D-glucarate) is generally in the range of 1500-3000 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 01:59:33 UTC 2023
Edited
by admin
on Thu Jul 06 01:59:33 UTC 2023
Record UNII
QLZ991V4A2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLUCARIC ACID
INCI  
INCI  
Official Name English
D-TETRAHYDROXYADIPIC ACID
Common Name English
D-SACCHARIC ACID
Common Name English
D-SACCHARATE
Common Name English
SACCHARIC ACID
Common Name English
D-(+)-SACCHARIC ACID
Common Name English
GLUCARIC ACID, D-
Common Name English
D-GLUCOSACCHARIC ACID
Common Name English
D-GLUCARIC ACID
MI  
Common Name English
GLUCARIC ACID [INCI]
Common Name English
D-GLUCARIC ACID [MI]
Common Name English
Code System Code Type Description
CHEBI
35392
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
CHEBI
17301
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
FDA UNII
QLZ991V4A2
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-768-1
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID60859455
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
CHEBI
33801
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
MESH
D005937
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
RXCUI
1788997
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
WIKIPEDIA
SACCHARIC ACID
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
MERCK INDEX
M5755
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY Merck Index
PUBCHEM
33037
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
CHEBI
16002
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
CAS
87-73-0
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
DRUG BANK
DB03603
Created by admin on Thu Jul 06 01:59:33 UTC 2023 , Edited by admin on Thu Jul 06 01:59:33 UTC 2023
PRIMARY
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