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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15NO6.H2O
Molecular Weight 239.2231
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-ACETYL-D-MANNOSAMINE HYDRATE

SMILES

O.CC(=O)N[C@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO

InChI

InChIKey=KVWIBLJBIFTKIZ-XNJRRJNCSA-N
InChI=1S/C8H15NO6.H2O/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11;/h2,5-8,11,13-15H,3H2,1H3,(H,9,12);1H2/t5-,6-,7-,8-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C8H15NO6
Molecular Weight 221.2078
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/25962821

N-acetylmannosamine (ManNAc), a hexosamine monosaccharide, is the first committed biological precursor of Neu5Ac. N-acetylmannosamine is being investigated as a potential treatment for GNE myopathy. N-acetylmannosamine has being reported to improve the cognitive function in aged animals. It has potential therapeutic application for cognitive dysfunction. N-acetylmannosamine is under investigation for GNE myopathy.

CNS Activity

Curator's Comment: N-acetylmannosamine (ManNAc) enhanced the hippocampal cell proliferation in mice. ManNAc had positive effects on the age-related brain dysfunction.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: D-glucose phosphorylation
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2585 ng/mL
10 g single, oral
dose: 10 g
route of administration: Oral
experiment type: SINGLE
co-administered:
N-ACETYLMANNOSAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14161 ng × h/mL
10 g single, oral
dose: 10 g
route of administration: Oral
experiment type: SINGLE
co-administered:
N-ACETYLMANNOSAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.4 h
10 g single, oral
dose: 10 g
route of administration: Oral
experiment type: SINGLE
co-administered:
N-ACETYLMANNOSAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
10 g single, oral
Highest studied dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.6, 20
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: myopathy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources: Page: p.6, 20
Other AEs: Diarrhea, Nausea...
Other AEs:
Diarrhea (50%)
Nausea (16.7%)
Sources: Page: p.6, 20
AEs

AEs

AESignificanceDosePopulation
Nausea 16.7%
10 g single, oral
Highest studied dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.6, 20
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: myopathy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources: Page: p.6, 20
Diarrhea 50%
10 g single, oral
Highest studied dose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.6, 20
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: myopathy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources: Page: p.6, 20
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
2-Acetamidoglucal, a new metabolite isolated from the urine of a patient with sialuria.
1979 Mar 22
Partial purification and properties of neuraminidase from Bifidobacterium lactentis.
1981 Feb
Synthesis of omega-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates.
1992 Jun 4
Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-alpha,beta-D-mannosamine as substrates for N-acetylneuraminic acid aldolase.
2001 May 18
Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts.
2002 Nov
No overall hyposialylation in hereditary inclusion body myopathy myoblasts carrying the homozygous M712T GNE mutation.
2005 Mar 4
Patents

Sample Use Guides

GNE myopathy or hereditary inclusion body myopathy: liquid solution of N-acetylmannosamine - 3,000 mg, 6,000 mg, and 10,000 mg orally
Route of Administration: Oral
In Vitro Use Guide
50uM of N-acetylmannosamine caused a reduction of total capillary length by 75% of the values obtained for spheroids, which were not co-stimulated with sialic acid precursors.
Substance Class Chemical
Created
by admin
on Sat Dec 16 13:34:44 UTC 2023
Edited
by admin
on Sat Dec 16 13:34:44 UTC 2023
Record UNII
FPD5WTK4TS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-ACETYL-D-MANNOSAMINE HYDRATE
Common Name English
D-MANNOSE, 2-(ACETYLAMINO)-2-DEOXY-, MONOHYDRATE
Common Name English
D-MANNOSE, 2-(ACETYLAMINO)-2-DEOXY-, HYDRATE (1:1)
Systematic Name English
N-ACETYL-D-MANNOSAMINE MONOHYDRATE
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1635
Created by admin on Sat Dec 16 13:34:44 UTC 2023 , Edited by admin on Sat Dec 16 13:34:44 UTC 2023
Code System Code Type Description
SMS_ID
100000183815
Created by admin on Sat Dec 16 13:34:44 UTC 2023 , Edited by admin on Sat Dec 16 13:34:44 UTC 2023
PRIMARY
FDA UNII
FPD5WTK4TS
Created by admin on Sat Dec 16 13:34:44 UTC 2023 , Edited by admin on Sat Dec 16 13:34:44 UTC 2023
PRIMARY
CAS
676347-48-1
Created by admin on Sat Dec 16 13:34:44 UTC 2023 , Edited by admin on Sat Dec 16 13:34:44 UTC 2023
PRIMARY Scifinder
PUBCHEM
22868018
Created by admin on Sat Dec 16 13:34:44 UTC 2023 , Edited by admin on Sat Dec 16 13:34:44 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE