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Details

Stereochemistry ACHIRAL
Molecular Formula C8H10N4O2
Molecular Weight 194.1906
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENPROFYLLINE

SMILES

CCCN1C2=C(N=CN2)C(=O)NC1=O

InChI

InChIKey=SIQPXVQCUCHWDI-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C8H10N4O2
Molecular Weight 194.1906
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Enprofylline is a xanthine derivative that shares theophylline's bronchodilator properties. It can be considered a relatively selective, though not potent adenosine A2B receptors antagonist. 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 the elevation in liver enzyme levels and unpredictable blood levels.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
156.0 µM [Ki]
32.0 µM [Ki]
7.0 µM [Ki]
65.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Palliative
Unknown
Palliative
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
The dosage of enprofylline was incremented from 150 mg twice daily at initiation to 300 and later 450 mg twice daily depending on the patient's tolerance.
Route of Administration: Oral
In Vitro Use Guide
Enprofylline antagonized the 5'-N-ethylcarboxamidoadenosine (NECA)-induced stimulation of platelet adenylate cyclase activity with a Kb of 130 microM. In human platelets, enprofylline did not antagonize but potentiated the NECA-induced inhibition of aggregation. This potentiation was abolished in the presence of the phosphodiesterase inhibitor papaverine. An adenosine antagonistic effect of enprofylline could not be evaluated on A2 receptors of the guinea-pig lung because the xanthine enhanced basal and NECA-stimulated cyclic AMP accumulation. Enprofylline antagonized the N6-R-(-)-phenylisopropyladenosine (R-PIA)-induced inhibition of rat fat cell adenylate cyclase with a Kb of 32 microM. The Ki value for inhibition of [3H]PIA binding to rat fat cell membranes was 45 microM. Enprofylline inhibited cyclic AMP phosphodiesterase activity of human platelets, guinea-pig lung and rat fat cells with Ki values of 15, 130 and 110 microM, respectively.
Substance Class Chemical
Record UNII
DT7DT5E518
Record Status Validated (UNII)
Record Version