ORAZAMIDE

Possibly Marketed Outside US

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 Search

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

Description
Sources: http://med.wanfangdata.com.cn/Paper/Detail?id=PeriodicalPaper_yydb201202020
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 4 Target ID: CHEMBL2111345 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15120611	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/535326	Primary		Not Provided 504	Orazamide Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of 5-aminoimidazole-4-carboxamide in human plasma by ion-pair extraction and LC-MS/MS.	2007 Aug 15	17561451

Patents

Sample Use Guides

In Vivo Use Guide

treatment group orally administered with orazamide tablets 0.3 g,tid

Route of Administration: Oral

In Vitro Use Guide

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

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