Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H18NO9.Na |
| Molecular Weight | 331.2517 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC(=O)N[C@H]([C@@H](O)CC(=O)C([O-])=O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI
InChIKey=MVHOXPMVPRDZIH-CBSHMQKXSA-M
InChI=1S/C11H19NO9.Na/c1-4(14)12-8(5(15)2-6(16)11(20)21)10(19)9(18)7(17)3-13;/h5,7-10,13,15,17-19H,2-3H2,1H3,(H,12,14)(H,20,21);/q;+1/p-1/t5-,7+,8+,9+,10+;/m0./s1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C11H18NO9 |
| Molecular Weight | 308.2619 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Aceneuramic acid (also known as N-Acetylneuraminic Acid, Neu5Ac, the UX 001 tablets) prolonged released had been filed a marketing authorization application with the European Medicines Agency by Ultragenyx in the EU for the treatment of hereditary inclusion body myopathy (HIBM), a rare, progressive muscle-wasting disease. This compound, a muscle protein stimulant, is also in phase II of the clinical trial for the treatment thrombocytopenia. In addition, recently was made studies, which had shown, that existed the significant positive correlation between serum and salivary sialic acid levels in oral squamous cell carcinoma (OSCC) patients.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.624 μg/mL |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACENEURAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
0.285 μg/mL |
2000 mg 3 times / day multiple, oral dose: 2000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACENEURAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.279 μg × h/mL |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACENEURAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
1.731 μg × h/mL |
2000 mg 3 times / day multiple, oral dose: 2000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACENEURAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.089 h |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACENEURAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
6 g 1 times / day steady, oral Highest studied dose Dose: 6 g, 1 times / day Route: oral Route: steady Dose: 6 g, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
2 g 3 times / day steady, oral Studied dose Dose: 2 g, 3 times / day Route: oral Route: steady Dose: 2 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Acute myocardial infarction, Gastritis... Other AEs: Acute myocardial infarction (serious, 2.2%) Sources: Gastritis (serious, 2.2%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Acute myocardial infarction | serious, 2.2% | 2 g 3 times / day steady, oral Studied dose Dose: 2 g, 3 times / day Route: oral Route: steady Dose: 2 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Gastritis | serious, 2.2% | 2 g 3 times / day steady, oral Studied dose Dose: 2 g, 3 times / day Route: oral Route: steady Dose: 2 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification and adipocyte differentiation-dependent expression of the unique disialic acid residue in an adipose tissue-specific glycoprotein, adipo Q. | 2001-08-03 |
|
| Differential contribution of sialic acid to the function of repolarizing K(+) currents in ventricular myocytes. | 2001-08 |
|
| A rapid, semi-automated method for detection of Galbeta1-4GlcNAc alpha2,6-sialyltransferase (EC 2.4.99.1) activity using the lectin Sambucus nigra agglutinin. | 2001-07 |
|
| Redirection of sialic acid metabolism in genetically engineered Escherichia coli. | 2001-07 |
|
| Characterization and mutagenesis of the recombinant N-acetylneuraminate lyase from Clostridium perfringens: insights into the reaction mechanism. | 2001-07 |
|
| Identification and characterization of S2V, a novel putative siglec that contains two V set Ig-like domains and recruits protein-tyrosine phosphatases SHPs. | 2001-06-29 |
|
| De novo synthesis of a methylene-bridged Neu5Ac-alpha-(2,3)-gal C-disaccharide. | 2001-06-15 |
|
| Overexpression of lysosomal-type sialidase leads to suppression of metastasis associated with reversion of malignant phenotype in murine B16 melanoma cells. | 2001-06-15 |
|
| Genomics. Are there bugs in our genome? | 2001-06-08 |
|
| Capillary electrophoresis of sialic acid-containing glycoprotein. Effect of the heterogeneity of carbohydrate chains on glycoform separation using an alpha1-acid glycoprotein as a model. | 2001-06-01 |
|
| Role of galactosylation in the renal pathogenicity of murine immunoglobulin G3 monoclonal cryoglobulins. | 2001-06-01 |
|
| N-acetylneuraminic acid (NANA) stimulates in situ cyclic AMP production in tentacles of sea anemone (Aiptasia pallida): possible role in chemosensitization of nematocyst discharge. | 2001-06 |
|
| Siglecs in the immune system. | 2001-06 |
|
| Effect of papaya seed extract on microenvironment of cauda epididymis. | 2001-06 |
|
| A longitudinal study of salivary sialic acid in preterm infants: Comparison of human milk-fed versus formula-fed infants. | 2001-06 |
|
| Metabolic selection of glycosylation defects in human cells. | 2001-06 |
|
| Dominant inheritance of sialuria, an inborn error of feedback inhibition. | 2001-06 |
|
| Neuraminidase from a bacterial source enhances both HIV-1-mediated syncytium formation and the virus binding/entry process. | 2001-05-25 |
|
| Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-alpha,beta-D-mannosamine as substrates for N-acetylneuraminic acid aldolase. | 2001-05-18 |
|
| Effects of sialic acid residues of transferrin on the binding with aluminum and iron studied by HPLC/high-resolution ICP-MS. | 2001-05-03 |
|
| Alcohol biomarkers: clinical significance and biochemical basis. | 2001-05 |
|
| Prenatal detection of free sialic acid storage disease: genetic and biochemical studies in nine families. | 2001-05 |
|
| Biochemical characterization and surfactant properties of horse allergens. | 2001-05 |
|
| Comparison of the sialic acid binding activity of transmissible gastroenteritis coronavirus and E. coli K99. | 2001-05 |
|
| Chemical derivatization of amino acids for in situ analysis of Martian samples by gas chromatography. | 2001-04-27 |
|
| Biochemical engineering of the side chain of sialic acids increases the biological stability of the highly sialylated cell adhesion molecule CEACAM1. | 2001-04-27 |
|
| A new fluorescent assay for sialyltransferase. | 2001-04-23 |
|
| Thermal stability of the hemagglutinin-neuraminidase from Sendai virus evidences two folding domains. | 2001-04-20 |
|
| Characterization of high-affinity binding between gangliosides and amyloid beta-protein. | 2001-04-15 |
|
| Corynebacterium diphtheriae surface proteins as adhesins to human erythrocytes. | 2001-04-13 |
|
| [The latest tumor marker in gastric cancer]. | 2001-04 |
|
| Sialyltransferase activity in normal and atherosclerotic human aorta intima. | 2001-04 |
|
| Evaluation of recurrence in 36 subacute thyroiditis patients managed with prednisolone. | 2001-04 |
|
| Novel erythropoiesis stimulating protein (NESP) for the treatment of anaemia of chronic disease associated with cancer. | 2001-04 |
|
| A dose-finding and safety study of novel erythropoiesis stimulating protein (NESP) for the treatment of anaemia in patients receiving multicycle chemotherapy. | 2001-04 |
|
| Pharmacokinetics of novel erythropoiesis stimulating protein (NESP) in cancer patients: preliminary report. | 2001-04 |
|
| Development and characterization of novel erythropoiesis stimulating protein (NESP). | 2001-04 |
|
| Investigating the paradox of hypothyroidism and increased serum thyrotropin (TSH) levels in Sheehan's syndrome: characterization of TSH carbohydrate content and bioactivity. | 2001-04 |
|
| Human FSH isoforms: carbohydrate complexity as determinant of in-vitro bioactivity. | 2001-03-28 |
|
| Multiple ligand binding sites on domain seven of human complement factor H. | 2001-03 |
|
| Modulating cell surface immunoreactivity by metabolic induction of unnatural carbohydrate antigens. | 2001-03 |
|
| Biochemical characterization of the soluble form of tumor antigen MUC1 isolated from sera and ascites fluid of breast and pancreatic cancer patients. | 2001-03 |
|
| Characterization of blood group ABO(H)-active gangliosides in type AB erythrocytes and structural analysis of type A-active ganglioside variants in type A human erythrocytes. | 2001-02-16 |
|
| The interaction of selective plant lectins with neuraminidase-treated and untreated IgA1 from the sera of IgA nephropathy patients. | 2001-02 |
|
| Biosynthesis of N-acetylneuraminic acid in cells lacking UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase. | 2001-02 |
|
| Glycoproteins from insect cells: sialylated or not? | 2001-02 |
|
| Post genome analysis of Campylobacter jejuni. | 2001 |
|
| Castration-induced hyperactivity of seminal vesicle in the catfish Clarias batrachus: a case of paradox and blockade by antiandrogen (cyproterone acetate) treatment. | 2001 |
|
| Characterizing glycosylation pathways. | 2001 |
|
| Electrophoretic and aggregation behavior of bovine, horse and human red blood cells in plasma and in polymer solutions. | 2001 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:49:07 GMT 2025
by
admin
on
Mon Mar 31 18:49:07 GMT 2025
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| Record UNII |
H87DON401P
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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H87DON401P
Created by
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101591028
Created by
admin on Mon Mar 31 18:49:07 GMT 2025 , Edited by admin on Mon Mar 31 18:49:07 GMT 2025
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126934-33-6
Created by
admin on Mon Mar 31 18:49:07 GMT 2025 , Edited by admin on Mon Mar 31 18:49:07 GMT 2025
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|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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