THEOPHYLLINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1940)
Entry Type: Small molecule
Molecule Category: Parent
ATC: R03DA04
UNII: 0I55128JYK

Structure
InChI Key ZFXYFBGIUFBOJW-UHFFFAOYSA-N
Smile Cn1c(=O)c2nc[nH]c2n(C)c1=O
InChI
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)

Physicochemical Descriptors

Property Name Value
Molecular Formula C7H8N4O2
Molecular Weight 180.17
AlogP -1.04
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 72.68
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 13.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Adenosine receptor antagonist PubMed PubMed PubMed PubMed Wikipedia
Primary Target
A2A receptor
A2B receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1A
- 92000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1B
- 92000 - - 46
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1C
- - - - 13
Enzyme Phosphodiesterase Phosphodiesterase 2 Phosphodiesterase 2A
- - - - 0
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3A
- - - - 30
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3B
- 90000 - 77000 30
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
- - - - 13
Enzyme Transferase
- 75000 - - -
Enzyme
- 50000-81000 - 56800-56800 26-39
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 7-7
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
28200 19000-28000 12000 700-26000 2100
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 1-90
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Unclassified protein
- - - 86400 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Pulmonary Disease, Chronic Obstructive 3 D029424 ClinicalTrials
Respiratory Insufficiency 3 D012131 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Kidney Diseases 2 D007674 ClinicalTrials
Altitude Sickness 2 D000532 ClinicalTrials
Virus Diseases 2 D014777 ClinicalTrials
Renal Insufficiency, Chronic 2 D051436 ClinicalTrials
Apnea 2 D001049 ClinicalTrials
Pseudohypoparathyroidism 2 D011547 ClinicalTrials
Hypertension, Pulmonary 1 D006976 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 1 D002289 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Depressive Disorder, Major 1 D003865 ClinicalTrials
Depressive Disorder 0 D003866 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Cardiac disorders Sinus tachycardia 100.0
Endocrine disorders Hyperglycaemia 98.0
Gastrointestinal disorders Vomiting 93.0
Cardiac disorders Sinus tachycardia 86.0
Metabolism and nutrition disorders Hypokalaemia 85.0
Metabolism and nutrition disorders Hypokalaemia 79.0
Gastrointestinal disorders Vomiting 73.0
Psychiatric disorders Nervousness 64.0
Psychiatric disorders Tension 64.0
Cardiac disorders Sinus tachycardia 62.0
Gastrointestinal disorders Vomiting 61.0
Metabolism and nutrition disorders Hypokalaemia 44.0
Metabolism and nutrition disorders Hypokalaemia 43.0
Vascular disorders Haemodynamic instability 40.0
Cardiac disorders Ventricular arrhythmia 40.0
Nervous system disorders Tremor 38.0
Gastrointestinal disorders Vomiting 30.0
Nervous system disorders Tremor 29.0
Gastrointestinal disorders Abdominal pain 21.0
Convulsion 21.0
Gastrointestinal disorders Gastrointestinal pain 21.0
Vascular disorders Hypotension 21.0
Psychiatric disorders Nervousness 21.0
Vascular disorders Shock 21.0
Cardiac disorders Supraventricular tachycardia 21.0
Cardiac disorders Tachycardia 21.0
Psychiatric disorders Tension 21.0
Cardiac disorders Ventricular extrasystoles 21.0
Cardiac disorders Ventricular extrasystoles 19.0
Endocrine disorders Hyperglycaemia 18.0
Nervous system disorders Tremor 16.0
Convulsion 14.0
Gastrointestinal disorders Diarrhoea 14.0
Vascular disorders Haemodynamic instability 14.0
Cardiac disorders Supraventricular tachycardia 14.0
Cardiac disorders Tachycardia 14.0
Nervous system disorders Tremor 14.0
Cardiac disorders Ventricular arrhythmia 14.0
Gastrointestinal disorders Abdominal pain 12.0
Cardiac disorders Atrial fibrillation 12.0
Cardiac disorders Cardiac flutter 12.0
Gastrointestinal disorders Gastrointestinal pain 12.0
Cardiac disorders Supraventricular tachycardia 12.0
Cardiac disorders Tachycardia 12.0
Nervous system disorders Disorientation 11.0
Convulsion 10.0
Cardiac disorders Ventricular extrasystoles 10.0
Vascular disorders Hypotension 8.0
Vascular disorders Shock 8.0
Nervous system disorders Disorientation 7.0
Vascular disorders Haemodynamic instability 7.0
Musculoskeletal and connective tissue disorders Rhabdomyolysis 7.0
Cardiac disorders Ventricular arrhythmia 7.0
Convulsion 5.0
Convulsion 4.0
Convulsion 3.0
Cardiac disorders Ventricular extrasystoles 3.0
Cardiac disorders Atrial tachycardia 2.0
Gastrointestinal disorders Haematemesis 2.0
Cardiac disorders Supraventricular tachycardia 2.0
Cardiac disorders Tachycardia 2.0
Cardiac disorders Atrial fibrillation 1.0
Cardiac disorders Cardiac flutter 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Respiratory, thoracic and mediastinal disorders
12.2
Nervous system disorders
10.51
Immune system disorders
9.51
Injury, poisoning and procedural complications
9.49
Cardiac disorders
9.08
General disorders and administration site conditions
8.1
Gastrointestinal disorders
6.09
Psychiatric disorders
5.96
Metabolism and nutrition disorders
5.46
Investigations
4.79
Vascular disorders
4.14
Eye disorders
3.53
Skin and subcutaneous tissue disorders
2.77
Infections and infestations
2.01

Cross References

Resources Reference
CAS NUMBER 58-55-9
ChEBI 28177
ChEMBL CHEMBL190
DrugBank DB00277
DrugCentral 2620
EPA CompTox DTXSID5021336
FDA SRS 0I55128JYK
Human Metabolome Database HMDB0001889
Guide to Pharmacology 413
KEGG C07130
PDB TEP
PharmGKB PA451647
PubChem 91268
SureChEMBL SCHEMBL4915
ZINC ZINC000018043251
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