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
UNII
TBT296U68M
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.