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Identification
- Generic Name
- AICA ribonucleotide
- DrugBank Accession Number
- DB01700
- Background
5-Aminoimidazole-4-carboxamide ribonucleotide (AICAR) is an intermediate in the generation of inosine monophosphate and analog of adenosine monophosphate (AMP) that is capable of stimulating AMP-dependent protein kinase (AMPK) activity. AICAR has been used clinically to treat and protect against cardiac ischemic injury. The drug was first used in the 1980s as a method to preserve blood flow to the heart during surgery and is currently of interest as a potential treatment for diabetes by increasing the metabolic activity of tissues by changing the physical composition of muscle.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for AICA ribonucleotide (DB01700)
- Weight
- Average: 338.2112
Monoisotopic: 338.062749988 - Chemical Formula
- C9H15N4O8P
- Synonyms
- 1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide
- 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
- 5-aminoimidazole-4-carboxamide ribotide
- 5-phosphoribosyl-4-carbamoyl-5-aminoimidazole
- 5'-phospho-ribosyl-5-amino-4-imidazole carboxamide
- 5'-phosphoribosyl-5-amino-4-imidazolecarboxamide
- acadesine 5'-monophosphate
- AICA-ribonucleotide
- AICAR
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBifunctional purine biosynthesis protein ATIC Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Adenylosuccinate Lyase Deficiency Disease Xanthine Dehydrogenase Deficiency (Xanthinuria) Disease Xanthinuria Type I Disease Mitochondrial DNA Depletion Syndrome Disease Myoadenylate Deaminase Deficiency Disease Purine Metabolism Metabolic Purine Nucleoside Phosphorylase Deficiency Disease Lesch-Nyhan Syndrome (LNS) Disease Gout or Kelley-Seegmiller Syndrome Disease Mercaptopurine Action Pathway Drug action Adenine Phosphoribosyltransferase Deficiency (APRT) Disease Adenosine Deaminase Deficiency Disease AICA-Ribosiduria Disease Molybdenum Cofactor Deficiency Disease Azathioprine Action Pathway Drug action Thioguanine Action Pathway Drug action Xanthinuria Type II Disease - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with AICA ribonucleotide. Acebutolol The therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Acebutolol. Acetazolamide The therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Acetazolamide. Acetohexamide The risk or severity of hypoglycemia can be increased when Acetohexamide is combined with AICA ribonucleotide. Acetyl sulfisoxazole The therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Acetyl sulfisoxazole. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Imidazole ribonucleosides and ribonucleotides
- Sub Class
- 1-ribosyl-imidazolecarboxamides
- Direct Parent
- 1-ribosyl-imidazolecarboxamides
- Alternative Parents
- Pentose phosphates / Glycosylamines / Monosaccharide phosphates / 2-heteroaryl carboxamides / Monoalkyl phosphates / Carbonylimidazoles / Aminoimidazoles / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds show 11 more
- Substituents
- 1,2-diol / 1-ribosyl-imidazolecarboxamide / 2-heteroaryl carboxamide / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aminoimidazole / Aromatic heteromonocyclic compound / Azacycle show 31 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- 1-(phosphoribosyl)imidazolecarboxamide, aminoimidazole (CHEBI:18406)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- F0X88YW0YK
- CAS number
- 3031-94-5
- InChI Key
- NOTGFIUVDGNKRI-UUOKFMHZSA-N
- InChI
- InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
- IUPAC Name
- {[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
- SMILES
- NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001517
- KEGG Compound
- C04677
- PubChem Compound
- 65110
- PubChem Substance
- 46508570
- ChemSpider
- 58620
- BindingDB
- 22579
- ChEBI
- 18406
- ChEMBL
- CHEMBL483849
- ZINC
- ZINC000004096500
- PDBe Ligand
- AMZ
- Wikipedia
- AICA_ribonucleotide
- PDB Entries
- 1m9n / 1p4r / 1pl0 / 2cnq / 2ntl / 2qre / 2r7k / 2r7l / 2r84 / 2uv5 … show 12 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.79 mg/mL ALOGPS logP -2.2 ALOGPS logP -4.8 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 1.22 Chemaxon pKa (Strongest Basic) 4.8 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 203.38 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 69.14 m3·mol-1 Chemaxon Polarizability 28.57 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.903 Blood Brain Barrier + 0.9226 Caco-2 permeable - 0.7239 P-glycoprotein substrate Non-substrate 0.7073 P-glycoprotein inhibitor I Non-inhibitor 0.8892 P-glycoprotein inhibitor II Non-inhibitor 0.9716 Renal organic cation transporter Non-inhibitor 0.9664 CYP450 2C9 substrate Non-substrate 0.8032 CYP450 2D6 substrate Non-substrate 0.8426 CYP450 3A4 substrate Non-substrate 0.6249 CYP450 1A2 substrate Non-inhibitor 0.8664 CYP450 2C9 inhibitor Non-inhibitor 0.9028 CYP450 2D6 inhibitor Non-inhibitor 0.9083 CYP450 2C19 inhibitor Non-inhibitor 0.8902 CYP450 3A4 inhibitor Non-inhibitor 0.9368 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.985 Ames test Non AMES toxic 0.8452 Carcinogenicity Non-carcinogens 0.8999 Biodegradation Not ready biodegradable 0.8328 Rat acute toxicity 2.4155 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9938 hERG inhibition (predictor II) Non-inhibitor 0.8014
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.8888132 predictedDarkChem Lite v0.1.0 [M-H]- 161.761 predictedDeepCCS 1.0 (2019) [M+H]+ 186.1473132 predictedDarkChem Lite v0.1.0 [M+H]+ 164.15659 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.0175132 predictedDarkChem Lite v0.1.0 [M+Na]+ 171.79063 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Bifunctional enzyme that catalyzes the last two steps of purine biosynthesis (PubMed:11948179, PubMed:14756554). Acts as a transformylase that incorporates a formyl group to the AMP analog AICAR (5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide) to produce the intermediate formyl-AICAR (FAICAR) (PubMed:10985775, PubMed:11948179, PubMed:9378707). Can use both 10-formyldihydrofolate and 10-formyltetrahydrofolate as the formyl donor in this reaction (PubMed:10985775). Also catalyzes the cyclization of FAICAR to IMP (PubMed:11948179, PubMed:14756554). Is able to convert thio-AICAR to 6-mercaptopurine ribonucleotide, an inhibitor of purine biosynthesis used in the treatment of human leukemias (PubMed:10985775). Promotes insulin receptor/INSR autophosphorylation and is involved in INSR internalization (PubMed:25687571)
- Specific Function
- Cadherin binding
- Gene Name
- ATIC
- Uniprot ID
- P31939
- Uniprot Name
- Bifunctional purine biosynthesis protein ATIC
- Molecular Weight
- 64615.255 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 28, 2022 01:12