AMINOPHYLLINE

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Trade Names
Synonyms
Status
Molecule Category Mixture
ATC R03DA05
UNII 27Y3KJK423
EPA CompTox DTXSID40883359

Structure

InChI Key FQPFAHBPWDRTLU-UHFFFAOYSA-N
Smiles Cn1c(=O)c2[nH]cnc2n(C)c1=O.Cn1c(=O)c2[nH]cnc2n(C)c1=O.NCCN
InChI
InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H24N10O4
Molecular Weight 420.43
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

Bioactivity

Mechanism of Action Action Reference
Adenosine receptor antagonist ANTAGONIST PubMed PubMed PubMed PubMed Wikipedia
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Organism : Homo sapiens
P27815 ENSG00000065989
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Organism : Homo sapiens
Q07343 ENSG00000184588
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4C
Organism : Homo sapiens
Q08493 ENSG00000105650
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Organism : Homo sapiens
Q08499 ENSG00000113448
Protein: Phosphodiesterase 3
Description: cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B
Organism : Homo sapiens
Q13370 ENSG00000152270
Protein: Phosphodiesterase 3
Description: cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
Organism : Homo sapiens
Q14432 ENSG00000172572
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 5 Cytochrome P450 family 5A Cytochrome P450 5A1
- - - - 0-0
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- - - - 34
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- - - - 34
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- - - - 34
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- - - - 34
Assay Description Organism Bioactivity Reference
Percent inhibition of bronchospasm, when administered orally at a dose of 160 mg/kg to guinea pig Cavia porcellus 81.0 %
Percent inhibition of bronchospasm, when administered orally at a dose of 18 mg/kg in guinea pig Cavia porcellus 21.0 %
Percent inhibition of bronchospasm, when administered orally at a dose of 53 mg/kg in guinea pig Cavia porcellus 55.0 %
Tested in vivo for anaphylactic bronchoconstriction in OA sensitized guinea pig at intraduodenal dose of 10 mg/kg for 30 min Cavia porcellus 42.0 %
Tested in vivo for histamine-induced bronchoconstriction in guinea pig at intraduodenal dose of 60 mg/kg Cavia porcellus 87.0 %
In vivo inhibitory effect on airway constriction induced by histamine 2-5 micro g/kg iv at 1 min after 10 mg/kg intravenous dose in anesthetized guinea pigs Cavia porcellus 86.0 %
In vivo inhibitory effect on airway constriction induced by histamine 2-5 micro g/kg iv at 1 min after 10 mg/kg iv dose of compound Cavia porcellus 86.0 %
Percent inhibition of Canine Tracheal Smooth Muscle PDE 4 at 100 uM Canis lupus familiaris 34.0 %
Tested in vitro against rabbit thromboxane A2 synthetase (TXA2) at 1 uM Oryctolagus cuniculus 0.0 %
Tested ex vivo against TXA2 production in rat serum at 1 hr after peroral dose of 30 mg/kg and anesthetized with ether None 0.0 %
Tested for inhibition of thromboxane A2 (TXA2) production in rabbit by in vitro assay at 1 uM Oryctolagus cuniculus 0.0 %
Tested for inhibition of thromboxane A2 (TXA2) production in rat serum by ex vivo assay after peroral dose of 30 mg/kg None 0.0 %
Inhibition of PDE in Sprague-Dawley rat epididymal adipose tissue assessed as [14C]adenosine recovery at 1 mM by liquid scintillation counting Rattus norvegicus 90.0 %
Inhibition of Ach-induced contraction in Sprague-Dawley rat trachea at 1 to 100 umol/L Rattus norvegicus 47.86 nM
Inhibition of Ach-induced contraction in Sprague-Dawley rat trachea Rattus norvegicus 50.0 nM

Cross References

Resources Reference
ChEBI 2659
ChEMBL CHEMBL1370561
DrugBank DB01223
FDA SRS 27Y3KJK423
PharmGKB PA164781029
PubChem 9433
SureChEMBL SCHEMBL5037
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