NAV

Enprofylline

Identification

Generic Name
Enprofylline
DrugBank Accession Number
DB00824
Background

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.

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 194.1906
Monoisotopic: 194.080375584
Chemical Formula
C8H10N4O2
Synonyms
  • 3-n-propylxanthine
  • 3-Propyl-3,7-dihydro-purine-2,6-dione
  • 3-propylxanthine
  • 3,7-dihydro-3-propyl-1H-purine-2,6-dione
  • Enprofilina
  • Enprofylline
  • Enprofyllinum
External IDs
  • D 4028
  • D-4028
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Used 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.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Enprofylline is a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine. It antagonizes erythrocyte phosphodiesterase, increasing cAMP activity.

Mechanism of action

Enprofylline 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.

TargetActionsOrganism
AcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Humans
AAdenosine receptor A2b
antagonist
Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4A
inhibitor
Humans
UAdenosine receptor A1
inhibitor
Humans
UAdenosine receptor A2a
inhibitor
Humans
UAdenosine receptor A3
inhibitor
Humans
Absorption

Rapidly absorbed from the digestive tract

Volume of distribution

Not Available

Protein binding

49%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

1.9 hours

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
Not Available
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Nilyph / Oxeze

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
oxopurine (CHEBI:126237)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
DT7DT5E518
CAS number
41078-02-8
InChI Key
SIQPXVQCUCHWDI-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

References

General References
Not Available
Human Metabolome Database
HMDB0014962
KEGG Drug
D04006
PubChem Compound
1676
PubChem Substance
46505790
ChemSpider
1613
BindingDB
50001493
ChEBI
126237
ChEMBL
CHEMBL279898
ZINC
ZINC000000403567
Therapeutic Targets Database
DAP001375
PharmGKB
PA164749350
Wikipedia
Enprofylline

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4WithdrawnTreatmentAsthma1
2Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SyrupOral800 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)287-289 °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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9303
CYP450 2C19 inhibitorNon-inhibitor0.912
CYP450 3A4 inhibitorNon-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
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-MSsplash10-016r-2900000000-c23c015100b016aff55f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-14948646871b497a248b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6900000000-f567262f42fc9578f666
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-e7ee2c7d5731b2fb5fec
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-4900000000-326759fd3a695efc26b1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-0900000000-77236c337d52ed14a218
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-7900000000-4bf55bfc4d85d50d3687
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-144.894083
predicted
DarkChem Lite v0.1.0
[M-H]-144.579683
predicted
DarkChem Lite v0.1.0
[M-H]-144.473383
predicted
DarkChem Lite v0.1.0
[M-H]-133.37401
predicted
DeepCCS 1.0 (2019)
[M+H]+145.197683
predicted
DarkChem Lite v0.1.0
[M+H]+144.708583
predicted
DarkChem Lite v0.1.0
[M+H]+144.670883
predicted
DarkChem Lite v0.1.0
[M+H]+137.20155
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.632083
predicted
DarkChem Lite v0.1.0
[M+Na]+144.796083
predicted
DarkChem Lite v0.1.0
[M+Na]+146.60397
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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 mediating central nervous system effects of therapeutic agents ranging f...
Gene Name
PDE4B
Uniprot ID
Q07343
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight
83342.695 Da
References
  1. Monteiro JP, Alves MG, Oliveira PF, Silva BM: Structure-Bioactivity Relationships of Methylxanthines: Trying to Make Sense of All the Promises and the Drawbacks. Molecules. 2016 Jul 27;21(8). pii: molecules21080974. doi: 10.3390/molecules21080974. [Article]
  2. Ukena D, Schudt C, Sybrecht GW: Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes. Biochem Pharmacol. 1993 Feb 24;45(4):847-51. [Article]
Details2. Adenosine receptor A2b
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2B
Uniprot ID
P29275
Uniprot Name
Adenosine receptor A2b
Molecular Weight
36332.655 Da
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. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details3. cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4A
Uniprot ID
P27815
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Molecular Weight
98142.155 Da
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. [Article]
  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. [Article]
  3. Dar MS: Central adenosinergic system involvement in ethanol-induced motor incoordination in mice. J Pharmacol Exp Ther. 1990 Dec;255(3):1202-9. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details4. Adenosine receptor A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Purine nucleoside binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
ADORA1
Uniprot ID
P30542
Uniprot Name
Adenosine receptor A1
Molecular Weight
36511.325 Da
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. [Article]
Details5. Adenosine receptor A2a
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Identical protein binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2A
Uniprot ID
P29274
Uniprot Name
Adenosine receptor A2a
Molecular Weight
44706.925 Da
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. [Article]
Details6. Adenosine receptor A3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction.
Gene Name
ADORA3
Uniprot ID
P0DMS8
Uniprot Name
Adenosine receptor A3
Molecular Weight
36184.175 Da
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45