U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H4N2O4.C4H6N4O
Molecular Weight 282.2129
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORAZAMIDE

SMILES

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

InChI

InChIKey=PVCSUEOGEIOUHG-UHFFFAOYSA-N
InChI=1S/C5H4N2O4.C4H6N4O/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)

HIDE SMILES / InChI

Molecular Formula C4H6N4O
Molecular Weight 126.1166
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H4N2O4
Molecular Weight 156.0963
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 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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:18:22 GMT 2023
Edited
by admin
on Fri Dec 15 16:18:22 GMT 2023
Record UNII
CLY9MRR8FV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORAZAMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
orazamide [INN]
Common Name English
ORAZAMIDE [MI]
Common Name English
Orazamide [WHO-DD]
Common Name English
5-AMINOIMIDAZOLE-4-CARBOXAMIDE OROTATE
Common Name English
ORAZAMIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2081
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
Code System Code Type Description
CAS
2574-78-9
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
MESH
C000259
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
FDA UNII
CLY9MRR8FV
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
SMS_ID
100000083323
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
INN
2957
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
DRUG CENTRAL
1994
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
PUBCHEM
167459
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
219-923-7
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
MERCK INDEX
m8226
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY Merck Index
EVMPD
SUB09452MIG
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
NCI_THESAURUS
C80155
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID40948614
Created by admin on Fri Dec 15 16:18:22 GMT 2023 , Edited by admin on Fri Dec 15 16:18:22 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS