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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H19NO9
Molecular Weight 309.2699
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACENEURAMIC ACID

SMILES

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=KBGAYAKRZNYFFG-BOHATCBPSA-N
InChI=1S/C11H19NO9/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)/t5-,7+,8+,9+,10+/m0/s1

HIDE SMILES / InChI
Molecular Formula C11H19NO9
Molecular Weight 309.2699
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Unknown
127998
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
651
Unknown

Approved Use

Unknown
Primary
Phase II
1133
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Characterizing glycosylation pathways.
2001
Electrophoretic and aggregation behavior of bovine, horse and human red blood cells in plasma and in polymer solutions.
2001
Sialoadhesin structure.
2001
Sialyltransferase activity in normal and atherosclerotic human aorta intima.
2001 Apr
Evaluation of recurrence in 36 subacute thyroiditis patients managed with prednisolone.
2001 Apr
Novel erythropoiesis stimulating protein (NESP) for the treatment of anaemia of chronic disease associated with cancer.
2001 Apr
Development and characterization of novel erythropoiesis stimulating protein (NESP).
2001 Apr
Corynebacterium diphtheriae surface proteins as adhesins to human erythrocytes.
2001 Apr 13
Characterization of high-affinity binding between gangliosides and amyloid beta-protein.
2001 Apr 15
Thermal stability of the hemagglutinin-neuraminidase from Sendai virus evidences two folding domains.
2001 Apr 20
Chemical derivatization of amino acids for in situ analysis of Martian samples by gas chromatography.
2001 Apr 27
Biochemical engineering of the side chain of sialic acids increases the biological stability of the highly sialylated cell adhesion molecule CEACAM1.
2001 Apr 27
Synthesis and biological evaluation of a sialyl Lewis X mimic with significantly improved E-selectin inhibition.
2001 Apr 9
Differential contribution of sialic acid to the function of repolarizing K(+) currents in ventricular myocytes.
2001 Aug
Biosynthesis of N-acetylneuraminic acid in cells lacking UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase.
2001 Feb
Glycoproteins from insect cells: sialylated or not?
2001 Feb
N-acetylgalactosamine, N-acetylglucosamine and sialic acid expression in primary breast cancers.
2001 Feb
Chronic postnatal administration of methylmalonic acid provokes a decrease of myelin content and ganglioside N-acetylneuraminic acid concentration in cerebrum of young rats.
2001 Feb
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 Feb 16
Structure of O-glycosidically linked oligosaccharides from glycoproteins of Trypanosoma cruzi CL-Brener strain: evidence for the presence of O-linked sialyl-oligosaccharides.
2001 Jan
Synthesis of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified at the C-4 and C-9 positions and their behaviour towards sialidase from influenza virus and pig liver membrane.
2001 Jan 15
Synthesis of novel ganglioside GM4 analogues containing N-deacetylated and lactamized sialic acid: probes for searching new ligand structures for human L-selectin.
2001 Jan 15
Sialic acid in human milk: composition and functions.
2001 Jan-Feb
Redirection of sialic acid metabolism in genetically engineered Escherichia coli.
2001 Jul
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 Jun
Siglecs in the immune system.
2001 Jun
Effect of papaya seed extract on microenvironment of cauda epididymis.
2001 Jun
Dominant inheritance of sialuria, an inborn error of feedback inhibition.
2001 Jun
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 Jun 1
Role of galactosylation in the renal pathogenicity of murine immunoglobulin G3 monoclonal cryoglobulins.
2001 Jun 1
Overexpression of lysosomal-type sialidase leads to suppression of metastasis associated with reversion of malignant phenotype in murine B16 melanoma cells.
2001 Jun 15
Exploring the acceptor substrate recognition of the human beta-galactoside alpha 2,6-sialyltransferase.
2001 Jun 15
Identification and characterization of S2V, a novel putative siglec that contains two V set Ig-like domains and recruits protein-tyrosine phosphatases SHPs.
2001 Jun 29
Binding of adeno-associated virus type 5 to 2,3-linked sialic acid is required for gene transfer.
2001 Jun 8
Multiple ligand binding sites on domain seven of human complement factor H.
2001 Mar
Modulating cell surface immunoreactivity by metabolic induction of unnatural carbohydrate antigens.
2001 Mar
Biochemical characterization of the soluble form of tumor antigen MUC1 isolated from sera and ascites fluid of breast and pancreatic cancer patients.
2001 Mar
Sialic acid-dependent binding of baculovirus-expressed recombinant antigens from Plasmodium falciparum EBA-175 to Glycophorin A.
2001 Mar
New functions for the sialic acid-binding adhesion molecule CD22, a member of the growing family of Siglecs.
2001 Mar
Effect of nitrofurazone on the reproductive organs in adult male mice.
2001 Mar
A comparative study of the asparagine-linked oligosaccharides on siglec-5, siglec-7 and siglec-8, expressed in a CHO cell line, and their contribution to ligand recognition.
2001 Mar
CD83 is an I-type lectin adhesion receptor that binds monocytes and a subset of activated CD8+ T cells [corrected].
2001 Mar 15
Pseudomonas aeruginosa infection of respiratory epithelium in a cystic fibrosis xenograft model.
2001 Mar 15
Synthesis of carbobicyclic compounds via palladium-catalyzed cyclization/hydrosilylation: evidence for reversible silylpalladation.
2001 Mar 9
Biochemical characterization and surfactant properties of horse allergens.
2001 May
Comparison of the sialic acid binding activity of transmissible gastroenteritis coronavirus and E. coli K99.
2001 May
Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-alpha,beta-D-mannosamine as substrates for N-acetylneuraminic acid aldolase.
2001 May 18
Neuraminidase from a bacterial source enhances both HIV-1-mediated syncytium formation and the virus binding/entry process.
2001 May 25
Effects of sialic acid residues of transferrin on the binding with aluminum and iron studied by HPLC/high-resolution ICP-MS.
2001 May 3
Metabolic control of recombinant protein N-glycan processing in NS0 and CHO cells.
2001 May 5
Patents

Patents

JP1055143A
2
JP1085924A
2
JP2000086687A
2
JP2000230931A
2
JP2000249710A
2
JP2001192402A
2
JP2001261705A
2
JP2001261706A
2
JP2002538183A
2
JP2002539204A
2
JP2003026648A
2
JP2003246792A
2
JP2006513142A
2
JP2006525796A
2
JP2007022940A
2
JP2008189635A
2
JP2009073845A
2
JP2009132727A
2
JP2009190993A
2
JP2009544680A
2
JP2010022253A
2
JP2010536929A
2
JP2011116736A
2
JP3238700B2
2
JP5360497B2
2
JPH01211499A
2
JPH02249968A
2
JPH03262495A
2
JPH05132496A
2
JPH05279379A
2
JPH0578381A
2
JPH06293788A
2
JPH06306092A
2
JPH07224100A
2
JPH08198892A
2
JPH09255576A
2
JPH10117795A
2
JPH10139774A
2
JPH1045602A
2
JPH11269190A
2
JPS60190787A
2
JPS61180719A
2
JPS62253399A
2
JPS6314793A
2
JPS63192399A
2
JPS6363697A
2
JPS6363972A
2
JPS6425716A
2

Sample Use Guides

In Vivo Use Guide
Subjects will take 4 tablets (500 mg aceneuramic acid extended-release (Ace-ER) each for 2 g per dose) orally 3 times per day (TID).The dose should be taken with food (i.e. within 30 minutes after a meal or snack).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 16 17:47:41 UTC 2022
Edited
by admin
on Fri Dec 16 17:47:41 UTC 2022
Record UNII
GZP2782OP0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACENEURAMIC ACID
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
5-N-ACETYLNEURAMINIC ACID
Common Name English
aceneuramic acid [INN]
Common Name English
ACENEURAMIC ACID [USAN]
Common Name English
SIALIC ACIDS N-ACETYLNEURAMINIC ACID
MI  
Common Name English
(2S,4S,5R,6R)-5-ACETAMIDO-2,4-DIHYDROXY- 6-((1R,2R)-1,2,3-TRIHYDROXYPROPYL)OXANE-2-CARBOXYLIC ACID
Systematic Name English
N-ACETYLNEURAMINIC ACID [USP-RS]
Common Name English
UX-001
Code English
N-ACETYLSIALIC ACID
Common Name English
D-GLYCERO-D-GALACTO-NONULOSONIC ACID, 5-ACETAMIDO-3,5-DIDEOXY-
Common Name English
Aceneuramic acid [WHO-DD]
Common Name English
UX001
Code English
(-)-5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID
Common Name English
LACTAMINIC ACID
Common Name English
ACETYLNEURAMINIC ACID
INCI  
INCI  
Official Name English
N-ACETYLNEURAMINIC ACID [MI]
Common Name English
D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID, 5-(ACETYLAMINO)-3,5-DIDEOXY-
Common Name English
ACETYLNEURAMINIC ACID [INCI]
Common Name English
N-ACETYLNEURAMIC ACID
Common Name English
ACENEURAMIC ACID [JAN]
Common Name English
N-ACETYL-D-NEURAMINIC ACID
Common Name English
SIALIC ACID
Common Name English
5-N-ACETYL-D-NEURAMINIC ACID
Common Name English
SIALIC ACIDS N-ACETYLNEURAMINIC ACID [MI]
Common Name English
NSC-111756
Code English
N-ACETYLNEURAMINIC ACID
MI   USP-RS  
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 351511
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
WHO-ATC M09AX05
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
NCI_THESAURUS C28188
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID0050425
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
CAS
489-46-3
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
NON-SPECIFIC STOICHIOMETRY
INN
6697
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
PUBCHEM
14017587
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
CHEBI
17012
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
USAN
CD-39
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
FDA UNII
GZP2782OP0
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
GRAS Notification (GRN No.)
602
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
ChEMBL
CHEMBL2105945
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
NCI_THESAURUS
C80777
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
EVMPD
SUB05210MIG
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
WIKIPEDIA
N-ACETYLNEURAMINIC ACID
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
DRUG BANK
DB11797
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
RS_ITEM_NUM
1612619
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
ECHA (EC/EINECS)
205-023-1
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
NSC
111756
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
MERCK INDEX
M9893
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY Merck Index
CAS
131-48-6
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
CAS
19342-33-7
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
ALTERNATIVE
CHEBI
173082
Created by admin on Fri Dec 16 17:47:41 UTC 2022 , Edited by admin on Fri Dec 16 17:47:41 UTC 2022
PRIMARY
Related Record Type Details
Structure of SODIUM ACENEURAMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ACENEURAMIC ACID
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