ISOBUTYLMETHYLXANTHINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H14N4O2
Molecular Weight	222.2438
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O

InChI

InChIKey=APIXJSLKIYYUKG-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C10H14N4O2
Molecular Weight	222.2438
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphodiesterase 1 12 Target ID: CHEMBL2097166 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8297	19.0 µM [IC50]
Phosphodiesterase 2A 7 Target ID: CHEMBL3477 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8297	50.0 µM [IC50]
Phosphodiesterase 3B 8 Target ID: CHEMBL5129 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8297	18.0 µM [IC50]
Phosphodiesterase 4 52 Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8297	13.0 µM [IC50]
Phosphodiesterase 5A 30 Target ID: CHEMBL3478 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8297	32.0 µM [IC50]

PubMed

Title	Date	PubMed
Insulin treatment improves islet function in type 2 diabetic Chinese hamsters.	2001	11453031
The expression and regulation of depolarization-activated K+ channels in the insulin-secreting cell line INS-1.	2001 Apr	11374068
Inhibition of rat cardiac fibroblast growth by cAMP--but not by cGMP-dependent protein kinase.	2001 Apr	11327337
Evaluation of signal transduction pathways in chemoattractant-induced human monocyte chemotaxis.	2001 Apr	11321360
Mechanisms of inverse agonism of antipsychotic drugs at the D(2) dopamine receptor: use of a mutant D(2) dopamine receptor that adopts the activated conformation.	2001 Apr	11299312
Human immunodeficiency virus type 1 Tat protein decreases cyclic AMP synthesis in rat microglia cultures.	2001 Apr	11299302
Signals from cone photoreceptors to L-type horizontal cells are differentially modulated by low calcium in carp retina.	2001 Apr	11298802
Cytokine induction of Fas gene expression in insulin-producing cells requires the transcription factors NF-kappaB and C/EBP.	2001 Aug	11473033
Platelet-derived growth factor stimulates phospholipase C-gamma 1, extracellular signal-regulated kinase, and arachidonic acid release in rat myometrial cells: contribution to cyclic 3',5'-adenosine monophosphate production and effect on cell proliferation.	2001 Aug	11466218
Members of the Kv1 and Kv2 voltage-dependent K(+) channel families regulate insulin secretion.	2001 Aug	11463864
Regulation of cAMP by light and dopamine receptors is dysfunctional in photoreceptors of dystrophic retinal degeneration slow(rds) mice.	2001 Aug	11446777
Mechanism for muscarinic inhibition of I(Ca(L)) is determined by the path for elevating cyclic AMP in cardiac myocytes.	2001 Aug 1	11470473
Persistent corticotropin-releasing factor(1) receptor desensitization and downregulation in the human neuroblastoma cell line IMR-32.	2001 Aug 15	11483248
The phorbol ester PMA and cyclic AMP activate different Cl(-) and HCO3(-) fluxes in C127 cells expressing CFTR.	2001 Feb 14	11342000
Effect of somatostatin on cholecystokinin-induced amylase release in rat pancreatic acini.	2001 Jul	11451139
Riboflavin uptake in human trophoblast-derived BeWo cell monolayers: cellular translocation and regulatory mechanisms.	2001 Jul	11408551
ClC-2 Cl- channels in human lung epithelia: activation by arachidonic acid, amidation, and acid-activated omeprazole.	2001 Jul	11401826
cAMP protection of pancreatic cancer cells against apoptosis induced by ERK inhibition.	2001 Jul 13	11444827
8-chloro-cAMP and 8-chloro-adenosine act by the same mechanism in multiple myeloma cells.	2001 Jul 15	11454694
Long-term hormonal regulation of the cAMP-specific phosphodiesterases in cultured FRTL-5 thyroid cells.	2001 Jul 25	11476896
Biphasic response to human galanin of extracellular acidification in human Bowes melanoma cells.	2001 Jul 6	11448477
Assessment of DNA damage in C6 glioma cells after antidepressant treatment using an alkaline comet assay.	2001 Jun	11482523
Prostaglandins and nitric oxide mediate superoxide-induced myocardial contractile dysfunction in isolated rat hearts.	2001 Jun	11444916
Expression and function of brain-derived neurotrophin factor and its receptor, TrkB, in ovarian follicles from the domestic hen (Gallus gallus domesticus).	2001 Jun	11441050
N-acetylneuraminic acid (NANA) stimulates in situ cyclic AMP production in tentacles of sea anemone (Aiptasia pallida): possible role in chemosensitization of nematocyst discharge.	2001 Jun	11441042
Role of cyclic nucleotide phosphodiesterase isoenzymes in contractile responses of denuded rat aorta related to various Ca2+ sources.	2001 Jun	11414656
Selective inhibition of beta(2)-adrenergic receptor-mediated cAMP generation by activation of the P2Y(2) receptor in mouse pineal gland tumor cells.	2001 Jun	11413231
Synergism between nitric oxide and hydrogen peroxide in the inhibition of platelet function: the roles of soluble guanylyl cyclase and vasodilator-stimulated phosphoprotein.	2001 Jun	11384196
Spontaneous and receptor-controlled soluble guanylyl cyclase activity in anterior pituitary cells.	2001 Jun	11376118
Insulin-stimulated hydrogen peroxide reversibly inhibits protein-tyrosine phosphatase 1b in vivo and enhances the early insulin action cascade.	2001 Jun 15	11297536
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.	2001 Mar	11465391
Generation of reactive oxygen species by xanthine derivatives in MDA-MB-231 human breast cancer cells.	2001 Mar	11437100
Monocyte chemoattractant protein-1 is expressed in pancreatic islets from prediabetic NOD mice and in interleukin-1 beta-exposed human and rat islet cells.	2001 Mar	11317664
Functional integrity of the vesicle transporting machinery is required for complete activation of cFTR expressed in xenopus laevis oocytes.	2001 Mar	11316271
Forskolin modulation of desensitization at GABA(A) and glycine receptors is not mediated by cAMP-dependent protein kinase in isolated carp amacrine-like cells.	2001 Mar	11316256
Ex vivo evidence that the phosphodiesterase inhibitor IBMX attenuates the up-regulation of PAR-2 in the endotoxemic rat aorta.	2001 Mar 15	11370637
Characterization of human, dog and rabbit corpus cavernosum type 5 phosphodiesterases.	2001 Mar 16	11388700
[Cyclonucleotide-dependent pathway--one of the mechanisms of olfactory transduction of the amino acid signal in Cyprinus carpio].	2001 Mar-Apr	11452779
The role of cyclic AMP in the pathogenesis of glucose desensitization in rat pancreatic islets.	2001 May	11345144
The Drosophila melanogaster homologue of an insect calcitonin-like diuretic peptide stimulates V-ATPase activity in fruit fly Malpighian tubules.	2001 May	11316500
Sonic hedgehog and FGF8: inadequate signals for the differentiation of a dopamine phenotype in mouse and human neurons in culture.	2001 May	11312556
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line.	2001 May	11295058
Rhythmicity of the cGMP-related signal transduction pathway in the mammalian circadian system.	2001 May	11294753
The influence of cAMP before or during bovine oocyte maturation on embryonic developmental competence.	2001 May 1	11393223
Gap junction-dependent increases in smooth muscle cAMP underpin the EDHF phenomenon in rabbit arteries.	2001 May 11	11341764
Functional consequences of the arrhythmogenic G306R KvLQT1 K+ channel mutant probed by viral gene transfer in cardiomyocytes.	2001 May 15	11351021
The role of cGMP hydrolysing phosphodiesterases 1 and 5 in cerebral artery dilatation.	2001 May 18	11412839
cAMP and excitability in neuroendocrine cells during reproductive senescence.	2001 May-Jun	11378258
Structure-activity and possible mode of action of S-Iamide neuropeptides on identified central neurons of Helix aspersa.	2001 Sep 15	11495688
Cystic fibrosis transmembrane regulator regulates uptake of sphingoid base phosphates and lysophosphatidic acid: modulation of cellular activity of sphingosine 1-phosphate.	2001 Sep 21	11443135

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:55 UTC 2023` Edited by `admin` on `Fri Dec 15 15:06:55 UTC 2023`
Record UNII	TBT296U68M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOBUTYLMETHYLXANTHINE

Systematic Name

English

3-ISOBUTYL-1-METHYLXANTHINE

Systematic Name

English

IBMX

Common Name

English

NSC-165960

Code

English

XANTHINE, 3-ISOBUTYL-1-METHYL-

Systematic Name

English

3,7-DIHYDRO-3-ISOBUTYL-1-METHYL-1H-PURINE-2,6-DIONE

Systematic Name

English

SC 2964

Code

English

3-ISOBUTYL-1-METHYL-XANTHINE

Systematic Name

English

SC-2964

Code

English

1-METHYL-3-ISOBUTYLXANTHINE

Systematic Name

English

1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1-METHYL-3-(2-METHYLPROPYL)-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

IBMX