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Identification
NameAicar
Accession NumberDB01700  (EXPT00407)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIF0X88YW0YK
CAS number3031-94-5
WeightAverage: 338.2112
Monoisotopic: 338.062749988
Chemical FormulaC9H15N4O8P
InChI KeyInChIKey=NOTGFIUVDGNKRI-BZKDHIKHSA-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+/m0/s1
IUPAC Name
{[(2S,3R,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)[[email protected]](O)[[email protected]]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1-phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide linked to a ribose phosphate through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-phosphoribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-phosphoribosyl-imidazolecarboxamide
  • 1-phosphoribosyl-imidazole
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Aminoimidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Myoadenylate deaminase deficiencyDiseaseSMP00537
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Azathioprine Action PathwayDrug actionSMP00427
Xanthinuria type IIDiseaseSMP00513
Purine MetabolismMetabolicSMP00050
Adenosine Deaminase DeficiencyDiseaseSMP00144
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Mitochondrial DNA depletion syndromeDiseaseSMP00536
AICA-RibosiduriaDiseaseSMP00168
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
Xanthinuria type IDiseaseSMP00512
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.903
Blood Brain Barrier+0.9226
Caco-2 permeable-0.7239
P-glycoprotein substrateNon-substrate0.7073
P-glycoprotein inhibitor INon-inhibitor0.8892
P-glycoprotein inhibitor IINon-inhibitor0.9716
Renal organic cation transporterNon-inhibitor0.9664
CYP450 2C9 substrateNon-substrate0.8032
CYP450 2D6 substrateNon-substrate0.8426
CYP450 3A4 substrateNon-substrate0.6249
CYP450 1A2 substrateNon-inhibitor0.8664
CYP450 2C9 inhibitorNon-inhibitor0.9028
CYP450 2D6 inhibitorNon-inhibitor0.9083
CYP450 2C19 inhibitorNon-inhibitor0.8902
CYP450 3A4 inhibitorNon-inhibitor0.9368
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.985
Ames testNon AMES toxic0.8452
CarcinogenicityNon-carcinogens0.8999
BiodegradationNot ready biodegradable0.8328
Rat acute toxicity2.4155 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9938
hERG inhibition (predictor II)Non-inhibitor0.8014
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.79 mg/mLALOGPS
logP-2.2ALOGPS
logP-4.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area203.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.14 m3·mol-1ChemAxon
Polarizability28.61 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AripiprazoleThe therapeutic efficacy of Aicar can be decreased when used in combination with Aripiprazole.
Arsenic trioxideThe therapeutic efficacy of Aicar can be decreased when used in combination with Arsenic trioxide.
ArticaineThe therapeutic efficacy of Aicar can be decreased when used in combination with Articaine.
AsenapineThe therapeutic efficacy of Aicar can be decreased when used in combination with Asenapine.
AtazanavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Atazanavir.
BendroflumethiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Bendroflumethiazide.
BetamethasoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Betamethasone.
BrexpiprazoleThe therapeutic efficacy of Aicar can be decreased when used in combination with Brexpiprazole.
BumetanideThe therapeutic efficacy of Aicar can be decreased when used in combination with Bumetanide.
BuserelinThe therapeutic efficacy of Aicar can be decreased when used in combination with Buserelin.
CeritinibThe therapeutic efficacy of Aicar can be decreased when used in combination with Ceritinib.
ChlorothiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Chlorothiazide.
ChlorpropamideAicar may increase the hypoglycemic activities of Chlorpropamide.
ChlorthalidoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Chlorthalidone.
ClozapineThe therapeutic efficacy of Aicar can be decreased when used in combination with Clozapine.
CorticotropinThe therapeutic efficacy of Aicar can be decreased when used in combination with Corticotropin.
Cortisone acetateThe therapeutic efficacy of Aicar can be decreased when used in combination with Cortisone acetate.
Cyproterone acetateThe therapeutic efficacy of Aicar can be decreased when used in combination with Cyproterone acetate.
DabrafenibThe therapeutic efficacy of Aicar can be decreased when used in combination with Dabrafenib.
DanazolThe therapeutic efficacy of Aicar can be decreased when used in combination with Danazol.
DarunavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Darunavir.
DesogestrelThe therapeutic efficacy of Aicar can be decreased when used in combination with Desogestrel.
DexamethasoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Dexamethasone.
DiazoxideThe therapeutic efficacy of Aicar can be decreased when used in combination with Diazoxide.
DienogestThe therapeutic efficacy of Aicar can be decreased when used in combination with Dienogest.
DisopyramideAicar may increase the hypoglycemic activities of Disopyramide.
DrospirenoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Drospirenone.
EpinephrineThe therapeutic efficacy of Aicar can be decreased when used in combination with Epinephrine.
EstradiolThe therapeutic efficacy of Aicar can be decreased when used in combination with Estradiol.
Estrone sulfateThe therapeutic efficacy of Aicar can be decreased when used in combination with Estrone sulfate.
Etacrynic acidThe therapeutic efficacy of Aicar can be decreased when used in combination with Etacrynic acid.
Ethinyl EstradiolThe therapeutic efficacy of Aicar can be decreased when used in combination with Ethinyl Estradiol.
Ethynodiol diacetateThe therapeutic efficacy of Aicar can be decreased when used in combination with Ethynodiol diacetate.
EtonogestrelThe therapeutic efficacy of Aicar can be decreased when used in combination with Etonogestrel.
EverolimusThe therapeutic efficacy of Aicar can be decreased when used in combination with Everolimus.
FludrocortisoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Fludrocortisone.
FosamprenavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Fosamprenavir.
FurosemideThe therapeutic efficacy of Aicar can be decreased when used in combination with Furosemide.
GliclazideAicar may increase the hypoglycemic activities of Gliclazide.
GlimepirideAicar may increase the hypoglycemic activities of Glimepiride.
GlipizideAicar may increase the hypoglycemic activities of Glipizide.
GlyburideAicar may increase the hypoglycemic activities of Glyburide.
GoserelinThe therapeutic efficacy of Aicar can be decreased when used in combination with Goserelin.
HistrelinThe therapeutic efficacy of Aicar can be decreased when used in combination with Histrelin.
HydrochlorothiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Hydrochlorothiazide.
HydrocortisoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Hydrocortisone.
HydroflumethiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Hydroflumethiazide.
Hydroxyprogesterone caproateThe therapeutic efficacy of Aicar can be decreased when used in combination with Hydroxyprogesterone caproate.
IloperidoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Iloperidone.
IndapamideThe therapeutic efficacy of Aicar can be decreased when used in combination with Indapamide.
IndinavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Indinavir.
Insulin AspartAicar may increase the hypoglycemic activities of Insulin Aspart.
Insulin DetemirAicar may increase the hypoglycemic activities of Insulin Detemir.
Insulin GlargineAicar may increase the hypoglycemic activities of Insulin Glargine.
Insulin GlulisineAicar may increase the hypoglycemic activities of Insulin Glulisine.
Insulin HumanAicar may increase the hypoglycemic activities of Insulin Human.
Insulin LisproAicar may increase the hypoglycemic activities of Insulin Lispro.
LanreotideThe therapeutic efficacy of Aicar can be decreased when used in combination with Lanreotide.
LanreotideAicar may increase the hypoglycemic activities of Lanreotide.
LeuprolideThe therapeutic efficacy of Aicar can be decreased when used in combination with Leuprolide.
LevonorgestrelThe therapeutic efficacy of Aicar can be decreased when used in combination with Levonorgestrel.
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Aicar.
LopinavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Lopinavir.
LurasidoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Lurasidone.
MecaserminAicar may increase the hypoglycemic activities of Mecasermin.
Medroxyprogesterone acetateThe therapeutic efficacy of Aicar can be decreased when used in combination with Medroxyprogesterone acetate.
Megestrol acetateThe therapeutic efficacy of Aicar can be decreased when used in combination with Megestrol acetate.
MestranolThe therapeutic efficacy of Aicar can be decreased when used in combination with Mestranol.
MethotrimeprazineThe therapeutic efficacy of Aicar can be decreased when used in combination with Methotrimeprazine.
MethyclothiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Methyclothiazide.
MethylprednisoloneThe therapeutic efficacy of Aicar can be decreased when used in combination with Methylprednisolone.
MetolazoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Metolazone.
MifepristoneAicar may increase the hypoglycemic activities of Mifepristone.
NateglinideAicar may increase the hypoglycemic activities of Nateglinide.
NelfinavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Nelfinavir.
NiacinThe therapeutic efficacy of Aicar can be decreased when used in combination with Niacin.
NilotinibThe therapeutic efficacy of Aicar can be decreased when used in combination with Nilotinib.
NorethisteroneThe therapeutic efficacy of Aicar can be decreased when used in combination with Norethisterone.
NorgestimateThe therapeutic efficacy of Aicar can be decreased when used in combination with Norgestimate.
OctreotideThe therapeutic efficacy of Aicar can be decreased when used in combination with Octreotide.
OctreotideAicar may increase the hypoglycemic activities of Octreotide.
OlanzapineThe therapeutic efficacy of Aicar can be decreased when used in combination with Olanzapine.
PaliperidoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Paliperidone.
PasireotideThe therapeutic efficacy of Aicar can be decreased when used in combination with Pasireotide.
PasireotideAicar may increase the hypoglycemic activities of Pasireotide.
PentamidineThe therapeutic efficacy of Aicar can be decreased when used in combination with Pentamidine.
PentamidineAicar may increase the hypoglycemic activities of Pentamidine.
PiperazineThe therapeutic efficacy of Aicar can be decreased when used in combination with Piperazine.
PipotiazineThe therapeutic efficacy of Aicar can be decreased when used in combination with Pipotiazine.
PolythiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Polythiazide.
PrednisoloneThe therapeutic efficacy of Aicar can be decreased when used in combination with Prednisolone.
PrednisoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Prednisone.
ProgesteroneThe therapeutic efficacy of Aicar can be decreased when used in combination with Progesterone.
QuetiapineThe therapeutic efficacy of Aicar can be decreased when used in combination with Quetiapine.
QuinethazoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Quinethazone.
QuinineAicar may increase the hypoglycemic activities of Quinine.
RepaglinideAicar may increase the hypoglycemic activities of Repaglinide.
RisperidoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Risperidone.
RitonavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Ritonavir.
SaquinavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Saquinavir.
SirolimusThe therapeutic efficacy of Aicar can be decreased when used in combination with Sirolimus.
SulfadiazineAicar may increase the hypoglycemic activities of Sulfadiazine.
SulfamethoxazoleAicar may increase the hypoglycemic activities of Sulfamethoxazole.
SulfisoxazoleAicar may increase the hypoglycemic activities of Sulfisoxazole.
SunitinibAicar may increase the hypoglycemic activities of Sunitinib.
TacrolimusThe therapeutic efficacy of Aicar can be decreased when used in combination with Tacrolimus.
TemsirolimusThe therapeutic efficacy of Aicar can be decreased when used in combination with Temsirolimus.
TipranavirThe therapeutic efficacy of Aicar can be decreased when used in combination with Tipranavir.
TolazamideAicar may increase the hypoglycemic activities of Tolazamide.
TolbutamideAicar may increase the hypoglycemic activities of Tolbutamide.
TorasemideThe therapeutic efficacy of Aicar can be decreased when used in combination with Torasemide.
TriamcinoloneThe therapeutic efficacy of Aicar can be decreased when used in combination with Triamcinolone.
TrichlormethiazideThe therapeutic efficacy of Aicar can be decreased when used in combination with Trichlormethiazide.
TriptorelinThe therapeutic efficacy of Aicar can be decreased when used in combination with Triptorelin.
VorinostatThe therapeutic efficacy of Aicar can be decreased when used in combination with Vorinostat.
ZiprasidoneThe therapeutic efficacy of Aicar can be decreased when used in combination with Ziprasidone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.Promotes insulin receptor/INSR autophosphorylation and is involved in INSR internalization (PubMed:25687571).
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular Weight:
64615.255 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23