diprophylline Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
N-methylated xanthine derivatives 976 479-18-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dyphylline
  • diprophylline
  • aristophyllin
  • corphyllin
  • diphyllin
  • diphylline
  • diprophyllin
  • glyphyllin
  • glyphylline
  • hidroxiteofillina
  • neophyllin
  • neutrafillina
  • neutraphyllin
  • neutraphylline
  • neutroxantina
  • protheophylline
  • propyphyllin
  • synthophylline
A THEOPHYLLINE derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis.
  • Molecular weight: 254.25
  • Formula: C10H14N4O4
  • CLOGP: -1.29
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 98.90
  • ALOGS: -1.25
  • ROTB: 3

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O
1 g P
1 g R

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 235.99 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.42 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.80 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 7, 1951 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC R03DA01 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
Xanthines
ATC R03DA51 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
Xanthines
ATC R03DB01 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
Xanthines and adrenergics
CHEBI has role CHEBI:35523 bronchodilator agents
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:50218 phosphodiesterase inhibitors
CHEBI has role CHEBI:51371 muscle relaxants
MeSH PA D018927 Anti-Asthmatic Agents
MeSH PA D001993 Bronchodilator Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D010726 Phosphodiesterase Inhibitors
MeSH PA D019141 Respiratory System Agents
MeSH PA D014665 Vasodilator Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchospasm indication 4386001
Chronic bronchitis indication 63480004 DOID:6132
Pulmonary emphysema indication 87433001
Asthma indication 195967001 DOID:2841
Asthma night-time symptoms indication 395022009
Asthma management indication 406162001
Asthma-chronic obstructive pulmonary disease overlap syndrome indication 10692761000119107
Chronic Obstructive Pulmonary Disease with Bronchospasms off-label use
COPD Associated with Chronic Bronchitis off-label use
Gastritis contraindication 4556007 DOID:4029
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Hyperammonemia contraindication 9360008
Peptic ulcer contraindication 13200003 DOID:750
Hepatic encephalopathy contraindication 13920009 DOID:13413
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Heart disease contraindication 56265001 DOID:114
Hepatic failure contraindication 59927004
Poisoning by phenobarbital contraindication 64921004
Substance abuse contraindication 66214007
Psychotic disorder contraindication 69322001
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050847
Cor pulmonale contraindication 83291003 DOID:8515
Kidney disease contraindication 90708001 DOID:557
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Dyspnea contraindication 267036007
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Angle-closure glaucoma contraindication 392291006 DOID:13550
Breastfeeding (mother) contraindication 413712001
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Porphyria contraindication 418470004
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.63 acidic
pKa2 13.91 acidic
pKa3 1.66 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
cGMP-inhibited 3',5'-cyclic phosphodiesterase A Enzyme INHIBITOR CHEMBL CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4B Enzyme INHIBITOR WOMBAT-PK CHEMBL

External reference:

IDSource
4018443 VUID
N0000146767 NUI
D00691 KEGG_DRUG
4018443 VANDF
C0013360 UMLSCUI
CHEBI:4728 CHEBI
X0T PDB_CHEM_ID
CHEMBL1752 ChEMBL_ID
CHEMBL221190 ChEMBL_ID
DB00651 DRUGBANK_ID
3182 PUBCHEM_CID
C010130 MESH_SUPPLEMENTAL_RECORD_UI
7070 IUPHAR_LIGAND_ID
1365 INN_ID
263T0E9RR9 UNII
3714 RXNORM
3397 MMSL
4648 MMSL
d00759 MMSL
000609 NDDF
32370002 SNOMEDCT_US
386183006 SNOMEDCT_US
D004400 MESH_DESCRIPTOR_UI

Pharmaceutical products:

None