CAS 41078-02-8|3-propylxanthine|3-n-PROPYLXANTHINE|3-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione|Enprofylline|3-propyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione|Enprofylline|3-propyl-1,9-dihydropurin...

General Information

Structure

Molecular Formula

C₈H₁₀N₄O₂

Molecular Mass

194.1906

Exact Mass

194.08037558

Charge

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)

InChIKey

SIQPXVQCUCHWDI-UHFFFAOYSA-N

Canonic Smiles

CCCn1c(=O)[nH]c(=O)c2c1nc[nH]2

Isomeric Smiles

O=c1n(CCC)c2nc[nH]c2c(=O)[nH]1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.23

LogD (pH = 5.5)

-0.12

Log P

-0.11

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.83

Polar Surface Area

78.09

Polarizability

18.72

Molar Refractivity

49.31

LOG S

-2.23

Data Source

Names and Identifiers

IUPAC Traditional name

3-propylxanthine 3-propyl-1,9-dihydropurine-2,6-dione enprofylline

Synonyms

3-n-PROPYLXANTHINEEnprofyllineEnprofylline3-PropylxanthineEnprofyllinum [INN-Latin]3-PropylxanthineEnprofilina [INN-Spanish]3-n-Propylxanthine3-Propyl-3,7-dihydro-purine-2,6-dione3-propylxanthineenprofylline3-n-propylxanthineEnprofylline3,7-dihydro-3-propyl-1H-purine-2,6-dione

IUPAC name

3-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione 3-propyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Brand Name

OxezeNilyph

API Name

Enprofylline

International Nonproprietary Name (INN)

enprofyllinumenprofyllineenprofilina

Names and Identifiers

Registration numbers

PubChem SID

160964166242776874650579085331227

PubChem CID

1676

CHEBI ID

126237CHEBI:126237CHEBI:665397

Unique Ingredient Identifier

DrugBank ID

Chemspider ID

CAS Number

EC Number

Wikipedia Title

CHEMBL

Beilstein Number

MDL Number

BRENDA Ligand Database

88886

BindingDB Database

50001493

SureChEMBL Database

SCHEMBL18029491SCHEMBL156402

BRENDA Database

2.7.1.35

CompTox Database

DTXSID9045186

BKMS React Database

88886

MetaboLights Database

MTBLS2145MTBLS1693MTBLS804

KEGG DRUG Database

D04006

Drug Central Database

1,015

ACToR Database

41078-02-8

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-0.2

Solubility

1200 mg/L

DMSO: soluble

H2O: slightly soluble (Solutions should be stored at 4°C.)

alcohol: soluble (Solutions should be stored at 4°C.)

Apperance

white solid

Product Information

Certificate of Analysis

Download link

Purity

≥99%

Pharmacology Properties

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE4B(5142)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00824

Drug Groups

approved

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.

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.

Pharmacology

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

Affected Organisms

Humans and other mammals

Absorption

Rapidly absorbed from the digestive tract

Half Life

1.9 hours

Protein Binding

49%

MP Biomedicals

02153779

Weak A1 and A2 adenosine receptor antagonist.

Wikipedia

Enprofylline

Sigma Aldrich

P5679

Biochem/physiol Actions
Weak competitive antagonist at both A1 and A2 adenosine receptors.

ChEBI

CHEBI:126237

Xanthine bearing a propyl substituent at position 3. A bronchodilator, it is used for the symptomatic treatment of asthma and chronic obstructive pulmonary disease, and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

3-propylxanthine 3-propyl-1,9-dihydropurine-2,6-dione enprofylline

Synonyms

IUPAC name

3-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione 3-propyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Brand Name

OxezeNilyph

API Name

Enprofylline

International Nonproprietary Name (INN)

enprofyllinumenprofyllineenprofilina

Registration numbers

PubChem SID

160964166242776874650579085331227

PubChem CID

1676

CHEBI ID

126237CHEBI:126237CHEBI:665397

Unique Ingredient Identifier

DrugBank ID

Chemspider ID

CAS Number

EC Number

Wikipedia Title

CHEMBL

Beilstein Number

MDL Number

BRENDA Ligand Database

88886

BindingDB Database

50001493

SureChEMBL Database

SCHEMBL18029491SCHEMBL156402

BRENDA Database

2.7.1.35

CompTox Database

DTXSID9045186

BKMS React Database

88886

MetaboLights Database

MTBLS2145MTBLS1693MTBLS804

KEGG DRUG Database

D04006

Drug Central Database

1,015

ACToR Database

41078-02-8

Molecule Details

DrugBank

DB00824

Drug Groups

approved

Description

Indication

Pharmacology

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

Affected Organisms

Humans and other mammals

Absorption

Rapidly absorbed from the digestive tract

Half Life

1.9 hours

Protein Binding

49%

MP Biomedicals

02153779

Weak A1 and A2 adenosine receptor antagonist.

Wikipedia