Details of the Drug

General Information of Drug (ID: DM46F5X)

Drug Name
isobutylmethylxanthine
Synonyms
3-Isobutyl-1-methylxanthine; IBMX; 28822-58-4; 1-METHYL-3-ISOBUTYLXANTHINE; Methylisobutylxanthine; 3-Isobutyl-1-methyl-1H-purine-2,6(3H,7H)-dione; Xanthine, 3-isobutyl-1-methyl-; 3-Isobutyl-1-methyxanthine; 1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-; Methyl-isobutylxanthine; 3-isobutyl-1-methylxanthine (ibmx); UNII-TBT296U68M; 3-Isobutyl 1-methylxanthine; NSC 165960; CCRIS 4290; CHEBI:34795; 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione; 3-isobutyl-1-methyl-7H-xanthine; methylisobutylxanthine; 3-Isobutyl-1-methyl-3,9-dihydro-purine-2,6-dione; 3-ISOBUTYL-1-METHYLXANTHINE
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 222.24
Logarithm of the Partition Coefficient (xlogp) 1.5
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Therapeutic agent toxicity Not Available SMPDL3A OTQDYH8E [2]
Chemical Identifiers
Formula
C10H14N4O2
IUPAC Name
1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
Canonical SMILES
CC(C)CN1C2=C(C(=O)N(C1=O)C)NC=N2
InChI
InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
InChIKey
APIXJSLKIYYUKG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3758
ChEBI ID
CHEBI:34795
CAS Number
28822-58-4
DrugBank ID
DB07954
TTD ID
D0R6MT

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Antagonist [3]
Adenosine A2a receptor (ADORA2A) TTM2AOE AA2AR_HUMAN Inhibitor [4]
Adenosine A2b receptor (ADORA2B) TTNE7KG AA2BR_HUMAN Inhibitor [5]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Inhibitor [5]
Phosphodiesterase 1 (PDE1) TTHQENC NOUNIPROTAC Inhibitor [6]
Phosphodiesterase 2A (PDE2A) TTJGW1Z PDE2A_HUMAN Inhibitor [7]
Phosphodiesterase 3A (PDE3A) TT06AWU PDE3A_HUMAN Inhibitor [6]
Phosphodiesterase 4A (PDE4A) TTZ97H5 PDE4A_HUMAN Inhibitor [6]
Phosphodiesterase 4B (PDE4B) TTVIAT9 PDE4B_HUMAN Inhibitor [6]
Phosphodiesterase 4D (PDE4D) TTSKMI8 PDE4D_HUMAN Inhibitor [7]
Phosphodiesterase 5A (PDE5A) TTJ0IQB PDE5A_HUMAN Inhibitor [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Adiponectin (ADIPOQ) OTNX23LE ADIPO_HUMAN Gene/Protein Processing [8]
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [9]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [10]
Choriogonadotropin subunit beta 3 (CGB3) OTVM2SU3 CGB3_HUMAN Protein Interaction/Cellular Processes [11]
Cyclic GMP-AMP phosphodiesterase SMPDL3A (SMPDL3A) OTQDYH8E ASM3A_HUMAN Drug Response [2]
Cystic fibrosis transmembrane conductance regulator (CFTR) OT6B22QH CFTR_HUMAN Gene/Protein Processing [12]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [13]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [14]
Fatty acid-binding protein, adipocyte (FABP4) OT3DKFOU FABP4_HUMAN Gene/Protein Processing [8]
Interleukin-2 receptor subunit alpha (IL2RA) OT0MWCHG IL2RA_HUMAN Gene/Protein Processing [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 388).
2 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
3 Species difference in the G protein selectivity of the human and bovine A1-adenosine receptor. J Biol Chem. 1994 Dec 23;269(51):32077-84.
4 Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors. J Med Chem. 1986 Jul;29(7):1305-8.
5 Adenosine receptors: targets for future drugs. J Med Chem. 1982 Mar;25(3):197-207.
6 A new generation of phosphodiesterase inhibitors: multiple molecular forms of phosphodiesterase and the potential for drug selectivity. J Med Chem. 1985 May;28(5):537-45.
7 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
8 Aloe-emodin inhibits adipocyte differentiation and maturation during in vitro human mesenchymal stem cell adipogenesis. J Biochem Mol Toxicol. 2012 Aug;26(8):291-300. doi: 10.1002/jbt.21415. Epub 2012 May 29.
9 The epidermal growth factor-like growth factor amphiregulin is strongly induced by the adenosine 3',5'-monophosphate pathway in various cell types. Endocrinology. 2004 Nov;145(11):5177-84. doi: 10.1210/en.2004-0232. Epub 2004 Jul 29.
10 Dual regulation of 2-adrenoceptor messenger RNA expression in human lung fibroblasts by 2-cAMP signaling; delayed upregulated inhibitors oppose a rapid in onset, direct stimulation of gene expression. Naunyn Schmiedebergs Arch Pharmacol. 2014 Jul;387(7):649-57. doi: 10.1007/s00210-014-0971-7. Epub 2014 Apr 8.
11 BLTK1 murine Leydig cells: a novel steroidogenic model for evaluating the effects of reproductive and developmental toxicants. Toxicol Sci. 2012 Jun;127(2):391-402. doi: 10.1093/toxsci/kfs121. Epub 2012 Mar 29.
12 Activation of CFTR by genistein in human airway epithelial cell lines. Biochem Biophys Res Commun. 2003 Aug 29;308(3):518-22. doi: 10.1016/s0006-291x(03)01436-0.
13 Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline. Xenobiotica. 2001 Mar;31(3):135-51.
14 Evaluation of estrogen receptor alpha activation by glyphosate-based herbicide constituents. Food Chem Toxicol. 2017 Oct;108(Pt A):30-42.
15 Pentoxifylline and other methyl xanthines inhibit interleukin-2 receptor expression in human lymphocytes. Cell Immunol. 1991 Jul;135(2):314-25. doi: 10.1016/0008-8749(91)90276-h.