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Identification
NameEnprofylline
Accession NumberDB00824  (APRD00273)
TypeSmall Molecule
GroupsApproved
Description

Enprofylline is a derivative of theophylline which shares bronchodilator properties. Enprofylline is used in asthma, chronic obstructive pulmonary disease, and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy. Long-term enprofylline administration may be associated with elevation in liver enzyme levels and unpredictable blood levels.

Structure
Thumb
Synonyms
SynonymLanguageCode
3-n-PropylxanthineNot AvailableNot Available
3-Propyl-3,7-dihydro-purine-2,6-dioneNot AvailableNot Available
3-PropylxanthineNot AvailableNot Available
3,7-dihydro-3-Propyl-1H-purine-2,6-dioneNot AvailableNot Available
EnprofilinaSpanishINN
EnprofyllineNot AvailableNot Available
EnprofyllinumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
NilyphNot Available
OxezeNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number41078-02-8
WeightAverage: 194.1906
Monoisotopic: 194.080375584
Chemical FormulaC8H10N4O2
InChI KeySIQPXVQCUCHWDI-UHFFFAOYSA-N
InChI
InChI=1S/C8H10N4O2/c1-2-3-12-6-5(9-4-10-6)7(13)11-8(12)14/h4H,2-3H2,1H3,(H,9,10)(H,11,13,14)
IUPAC Name
3-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CCCN1C2=C(NC=N2)C(=O)NC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Xanthine
  • Purinone
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed in the management of symptoms of asthma. Also used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
PharmacodynamicsEnprofylline is a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine. It antagonizes erythrocyte phosphodiesterase, increasing cAMP activity.
Mechanism of actionEnprofylline inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity. Along with erythrocyte activity, enprofylline also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity.
AbsorptionRapidly absorbed from the digestive tract
Volume of distributionNot Available
Protein binding49%
Metabolism
Route of eliminationNot Available
Half life1.9 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8963
Caco-2 permeable-0.6282
P-glycoprotein substrateSubstrate0.6567
P-glycoprotein inhibitor INon-inhibitor0.7819
P-glycoprotein inhibitor IINon-inhibitor0.9559
Renal organic cation transporterNon-inhibitor0.796
CYP450 2C9 substrateNon-substrate0.7883
CYP450 2D6 substrateNon-substrate0.8691
CYP450 3A4 substrateNon-substrate0.5557
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9303
CYP450 2C19 substrateNon-inhibitor0.912
CYP450 3A4 substrateNon-inhibitor0.9561
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9259
Ames testNon AMES toxic0.73
CarcinogenicityNon-carcinogens0.9402
BiodegradationNot ready biodegradable0.7406
Rat acute toxicity2.6371 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6953
hERG inhibition (predictor II)Non-inhibitor0.7663
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point287-289 °CPhysProp
water solubility1200 mg/LNot Available
logP0.33SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility5.68 mg/mLALOGPS
logP0.35ALOGPS
logP-0.11ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.83ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.09 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.31 m3·mol-1ChemAxon
Polarizability18.72 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4B Q07343 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Adenosine receptor A2b

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Adenosine receptor A2b P29275 Details

References:

  1. Holgate ST: The Quintiles Prize Lecture 2004. The identification of the adenosine A2B receptor as a novel therapeutic target in asthma. Br J Pharmacol. 2005 Aug;145(8):1009-15. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4A P27815 Details

References:

  1. Featherstone RL, Chambers DJ: Long-term hypothermic lung preservation: does adenosine A1 receptor antagonism have a role in ischemic preconditioning protection? Interact Cardiovasc Thorac Surg. 2004 Mar;3(1):182-7. Pubmed
  2. Dulloo AG, Seydoux J, Girardier L: Peripheral mechanisms of thermogenesis induced by ephedrine and caffeine in brown adipose tissue. Int J Obes. 1991 May;15(5):317-26. Pubmed
  3. Dar MS: Central adenosinergic system involvement in ethanol-induced motor incoordination in mice. J Pharmacol Exp Ther. 1990 Dec;255(3):1202-9. Pubmed
  4. Ukena D, Schirren CG, Schwabe U: Effects of enprofylline on A1 and A2 adenosine receptors. Eur J Pharmacol. 1985 Oct 29;117(1):25-33. Pubmed
  5. Berg G, Andersson RG, Ryden G: Effects of different phosphodiesterase-inhibiting drugs on human pregnant myometrium: an in vitro study. Arch Int Pharmacodyn Ther. 1987 Dec;290(2):288-92. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Adenosine receptor A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenosine receptor A1 P30542 Details

References:

  1. Linden J, Thai T, Figler H, Jin X, Robeva AS: Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells. Mol Pharmacol. 1999 Oct;56(4):705-13. Pubmed

5. Adenosine receptor A2a

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenosine receptor A2a P29274 Details

References:

  1. Linden J, Thai T, Figler H, Jin X, Robeva AS: Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells. Mol Pharmacol. 1999 Oct;56(4):705-13. Pubmed

6. Adenosine receptor A3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenosine receptor A3 P33765 Details

References:

  1. Linden J, Thai T, Figler H, Jin X, Robeva AS: Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells. Mol Pharmacol. 1999 Oct;56(4):705-13. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on November 07, 2013 17:26