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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4N2O4.C4H6N4O.2H2O
Molecular Weight 318.2435
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORAZAMIDE DIHYDRATE

SMILES

O.O.NC(=O)C1=C(N)NC=N1.OC(=O)C2=CC(=O)NC(=O)N2

InChI

InChIKey=RAZMBRTXTADRMQ-UHFFFAOYSA-N
InChI=1S/C5H4N2O4.C4H6N4O.2H2O/c8-3-1-2(4(9)10)6-5(11)7-3;5-3-2(4(6)9)7-1-8-3;;/h1H,(H,9,10)(H2,6,7,8,11);1H,5H2,(H2,6,9)(H,7,8);2*1H2

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17561451 | https://www.ncbi.nlm.nih.gov/pubmed/535326 | https://www.ncbi.nlm.nih.gov/pubmed/15120611

Orazamide, which is composed of one molecule of 5-aminoimidazole-4-carboxamide (AICA), one molecule of orotic acid and two molecules of water, is used clinically for the treatment of hepatitis and cirrhosis The nucleoside of AICA (AICAR) is internalized and becomes phosphorylated by adenosine kinase to form AICAR mono-phosphate (AICA ribotide, ZMP), an intermediate in the late steps of de novo purine biosynthesis. In hepatocytes, AICA can inhibit the fatty acid synthesis, sterol synthesis, and gluconeogenesis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Orazamide

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Determination of 5-aminoimidazole-4-carboxamide in human plasma by ion-pair extraction and LC-MS/MS.
2007 Aug 15
Patents

Patents

Sample Use Guides

treatment group orally administered with orazamide tablets 0.3 g,​tid
Route of Administration: Oral
For analysis of TNF-alpha, macrophages were plated onto either 24-well or 6-well tissue culture plates. Cells (1.5x10^6 cells/ml) were treated with various concentrations (0.1, 0.5 and 1 mM) of AICAR (5-aminoimidazole-4-carboxamide) and LPS, as indicated. The quantity of TNF-a in culture supernatants was measured with an ELISA kit, according to the manufacturer’s instructions. The concentrations of TNF-a in each sample were calculated from a standard curve prepared using known concentrations of recombinant TNF- alpha.
Name Type Language
ORAZAMIDE DIHYDRATE
MI  
Common Name English
ORAZAMIDE DIHYDRATE [MI]
Common Name English
1H-IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-, MONO(1,2,3,6-TETRAHYDRO-2,6-DIOXO-4-PYRIMIDINECARBOXYLATE), DIHYDRATE
Common Name English
4-PYRIMIDINECARBOXYLIC ACID, 1,2,3,6-TETRAHYDRO-2,6-DIOXO-, COMPD. WITH 5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE, HYDRATE (1:1:2)
Common Name English
4-PYRIMIDINECARBOXYLIC ACID, 1,2,3,6-TETRAHYDRO-2,6-DIOXO-, COMPD. WITH 5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE (1:1), DIHYDRATE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID60975528
Created by admin on Sat Dec 16 04:29:17 GMT 2023 , Edited by admin on Sat Dec 16 04:29:17 GMT 2023
PRIMARY
PUBCHEM
102285
Created by admin on Sat Dec 16 04:29:17 GMT 2023 , Edited by admin on Sat Dec 16 04:29:17 GMT 2023
PRIMARY
FDA UNII
7793E20Q84
Created by admin on Sat Dec 16 04:29:17 GMT 2023 , Edited by admin on Sat Dec 16 04:29:17 GMT 2023
PRIMARY
MERCK INDEX
m8226
Created by admin on Sat Dec 16 04:29:17 GMT 2023 , Edited by admin on Sat Dec 16 04:29:17 GMT 2023
PRIMARY Merck Index
CAS
60104-30-5
Created by admin on Sat Dec 16 04:29:17 GMT 2023 , Edited by admin on Sat Dec 16 04:29:17 GMT 2023
PRIMARY