Identification

Generic Name
3-isobutyl-1-methyl-7H-xanthine
DrugBank Accession Number
DB07954
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 222.2438
Monoisotopic: 222.111675712
Chemical Formula
C10H14N4O2
Synonyms
  • 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
  • 1-methyl-3-isobutylxanthine
  • 3-isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione
  • 3-isobutyl-1-methylxanthine
  • 3-Isobutyl-1-methyxanthine
  • IBMX
External IDs
  • NSC-165960
  • SC 2964
  • SC-2964

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UcGMP-specific 3',5'-cyclic phosphodiesteraseNot AvailableHumans
UcGMP-inhibited 3',5'-cyclic phosphodiesterase BNot AvailableHumans
UHigh affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7ANot AvailableHumans
UcAMP-specific 3',5'-cyclic phosphodiesterase 4DNot AvailableHumans
UHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9ANot AvailableHumans
UHigh affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8ANot AvailableHumans
UcGMP-dependent 3',5'-cyclic phosphodiesteraseNot AvailableHumans
URetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaNot AvailableHumans
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
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
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.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
AbirateroneThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with 3-isobutyl-1-methyl-7H-xanthine.
AcetazolamideAcetazolamide may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
AdalimumabThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be decreased when it is combined with Adalimumab.
AdenosineThe therapeutic efficacy of Adenosine can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
AllopurinolThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Allopurinol.
AlprazolamThe therapeutic efficacy of Alprazolam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
AmiodaroneThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Amiodarone.
AmobarbitalThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be decreased when it is combined with Amobarbital.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Lactam / Organic nitrogen compound
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
3-isobutyl-1-methylxanthine (CHEBI:43253) / a small molecule (CPD-5461)
Affected organisms
Not Available

Chemical Identifiers

UNII
TBT296U68M
CAS number
28822-58-4
InChI Key
APIXJSLKIYYUKG-UHFFFAOYSA-N
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)
IUPAC Name
1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione
SMILES
CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O

References

General References
Not Available
KEGG Compound
C13708
PubChem Compound
3758
PubChem Substance
99444425
ChemSpider
3627
BindingDB
50027176
ChEBI
34795
ChEMBL
CHEMBL275084
ZINC
ZINC000003861807
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
IBM
Wikipedia
IBMX
PDB Entries
1rkp / 1soj / 1zkl / 1zkn / 2hd1 / 2r8q / 2yy2 / 3dy8 / 3dyl / 3dyn
show 9 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility5.44 mg/mLALOGPS
logP0.84ALOGPS
logP0.44ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)11.41ChemAxon
pKa (Strongest Basic)2.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.37 m3·mol-1ChemAxon
Polarizability22.52 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.989
Caco-2 permeable-0.5131
P-glycoprotein substrateNon-substrate0.5833
P-glycoprotein inhibitor INon-inhibitor0.7453
P-glycoprotein inhibitor IIInhibitor0.5777
Renal organic cation transporterNon-inhibitor0.8472
CYP450 2C9 substrateNon-substrate0.816
CYP450 2D6 substrateNon-substrate0.8375
CYP450 3A4 substrateSubstrate0.5588
CYP450 1A2 substrateInhibitor0.8472
CYP450 2C9 inhibitorNon-inhibitor0.9159
CYP450 2D6 inhibitorNon-inhibitor0.9667
CYP450 2C19 inhibitorNon-inhibitor0.9664
CYP450 3A4 inhibitorNon-inhibitor0.8583
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.955
Ames testNon AMES toxic0.7455
CarcinogenicityNon-carcinogens0.9232
BiodegradationNot ready biodegradable0.6337
Rat acute toxicity3.3966 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8844
hERG inhibition (predictor II)Non-inhibitor0.6887
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-3900100000-d4f10d08f06745544691

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase b binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. May play a role in fat metab...
Gene Name
PDE3B
Uniprot ID
Q13370
Uniprot Name
cGMP-inhibited 3',5'-cyclic phosphodiesterase B
Molecular Weight
124332.145 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name
PDE7A
Uniprot ID
Q13946
Uniprot Name
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
Molecular Weight
55504.475 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4D
Uniprot ID
Q08499
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Molecular Weight
91114.1 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Specifically hydrolyzes the second messenger cGMP, which is a key regulator of many important physiological processes. Highly specific: compared to other members of the cyclic nucleotide phosphodie...
Gene Name
PDE9A
Uniprot ID
O76083
Uniprot Name
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A
Molecular Weight
68491.95 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in maintaining basal levels of the cyclic nucleotide and/or in the cAMP reg...
Gene Name
PDE8A
Uniprot ID
O60658
Uniprot Name
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A
Molecular Weight
93303.05 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tpr domain binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.Isoform PDE2A2: Regulates Mit...
Gene Name
PDE2A
Uniprot ID
O00408
Uniprot Name
cGMP-dependent 3',5'-cyclic phosphodiesterase
Molecular Weight
105715.85 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Enzyme inhibitor activity
Specific Function
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name
PDE6G
Uniprot ID
P18545
Uniprot Name
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma
Molecular Weight
9643.09 Da
References
  1. 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 September 15, 2010 21:27 / Updated at June 12, 2020 16:52