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Identification
Name Aminophylline
Accession Number DB01223 (APRD00329)
Type small molecule
Groups approved
Description

Aminophylline is a drug combination that contains theophylline and ethylenediamine in 2:1 ratio. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Aminophyllin
Aminophylline Anhydrous
Aminophylline Dihydrate
Aminophylline Dye Free
Salts Not Available
Brand names
Name Company
Aminocardol
Aminodur
Ammophyllin
Cardiofilina
Cardiomin
Cardophylin
Cardophyllin
Carena
Cariomin
Diaphylline
Diophllin
Diuxanthine
Dobo
Dura-Tab S.M. Aminophylline
Ethophylline
Etilen-Xantisan Tabl.
Eurphyllin
Euufillin
Genophyllin
Grifomin
Inophylline
Lasodex
Linampheta
Lixaminol
Metaphyllin
Metaphylline
Methophylline
Minaphil
Miofilin
Neophyiline
Norofilina
Peterphyllin
Phylcardin
Phyllindon
Phyllocontin
Phyllocontin-350
Rectalad Aminophylline
Rectalad-Aminophylline
Somophyllin
Somophyllin O
Somophyllin-O
Stenovasan
Syntophyllin
Theodrox
Theolamine
Theolone
Theophyldine
Theophyline Ethylenediamine
Theophyllamine
Theophyllaminum
Theophyllin Aethylendiamin
Theophyllin Ethylenediamine
Theophylline Ethylenediamine
Thephyldine
Truphylline
Variaphylline
Vasofilina
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Ami-Nesine Liq Aminophylline + Guaifenesin
Quiex - Forte Syr Aminophylline + Guaifenesin
Quiex Liq Aminophylline + Guaifenesin
Quiex-K1 Syr Aminophylline + Guaifenesin + Potassium Iodide
Quiex-Pred Sus Aminophylline + Guaifenesin + Prednisolone
Categories
  • Phosphodiesterase Inhibitors
  • Bronchodilator Agents
  • Cardiotonic Agents
  • Respiratory Smooth Muscle Relaxants
CAS number 317-34-0
Weight Average: 420.4264
Monoisotopic: 420.198199306
Chemical Formula C16H24N10O4
InChI Key InChIKey=FQPFAHBPWDRTLU-UHFFFAOYSA-N
InChI
InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2
Plain Text
IUPAC Name
bis(1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione); ethane-1,2-diamine
SMILES
NCCN.CN1C2=C(NC=N2)C(=O)N(C)C1=O.CN1C2=C(NC=N2)C(=O)N(C)C1=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Xanthines
Substructures
  • Aliphatic and Aryl Amines
  • Xanthines
  • Pyrimidines and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Purines and Purine Derivatives
  • Cyanamides
Pharmacology
Indication For the treatment of bronchospasm due to asthma, emphysema and chronic bronchitis.
Pharmacodynamics Aminophylline is the ethylenediamine salt of theophylline. Theophylline stimulates the CNS, skeletal muscles, and cardiac muscle. It relaxes certain smooth muscles in the bronchi through PDE3 inhibition, produces diuresis, and causes an increase in gastric secretion.
Mechanism of action Theophylline is structurally related to theobromine and caffeine. The precise mechanism of action of theophylline is not known, however, it is thought to be a phosphodiesterase inhibitor which may give a bronchodilatory effect. It also binds adenosine receptors.
Absorption Not Available
Volume of distribution
  • 0.3 to 0.7 L/kg
Protein binding 60%
Metabolism Not Available
Route of elimination Not Available
Half life 7-9 hours
Clearance
  • 0.29 mL/kg/min [postnatal age 3-15 days]
  • 0.64 mL/kg/min [postnatal age 25-57 days]
  • 1.7 mL/kg/min [ 1-4 years]
  • 1.6 mL/kg/min [4-12 years]
  • 0.9 mL/kg/min [13-15 years]
  • 1.4 mL/kg/min [16-17 years]
  • 0.65 mL/kg/min [Adults (16-60 years), non-smoking asthmatics]
  • 0.41 mL/kg/min [Elderly (>60 years). liver, and renal function]
  • 0.33 mL/kg/min [Acute pulmonary edema]
  • 0.54 mL/kg/min [COPD→60 years, stable non-smoker >1 year]
  • 0.48 mL/kg/min [COPD with cor pulmonale]
  • 1.25 mL/kg/min [Cystic fibrosis (14-28 years)]
  • 0.31 mL/kg/min [Liver disease -cholestasis]
  • 0.35 mL/kg/min [cirrhosis]
  • 0.65 mL/kg/min [acute hepatitis]
  • 0.47 mL/kg/min [Sepsis with multi-organ failure]
  • 0.38 mL/kg/min [hypothyroid]
  • 0.8 mL/kg/min [hyperthyroid]
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Fisons corp
  • Gd searle llc
  • Abraxis pharmaceutical products
  • Elkins sinn div ah robins co inc
  • Hospira inc
  • International medication system
  • International medication systems ltd
  • King pharmaceuticals inc
  • Luitpold pharmaceuticals inc
  • Pharma serve inc sub torigian laboratories
  • Smith and nephew solopak div smith and nephew
  • Teva parenteral medicines inc
  • Morton grove pharmaceuticals inc
  • Roxane laboratories inc
  • Actavis mid atlantic llc
  • G and w laboratories inc
  • Impax laboratories inc
  • Tablicaps inc
  • Vale chemical co inc
  • Pharmaceutical research assoc inc
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Barr laboratories inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Halsey drug co inc
  • Kv pharmaceutical co
  • Lannett co inc
  • Pal pak inc
  • Panray corp sub ormont drug and chemical co inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Valeant pharmaceuticals international
  • Vangard laboratories inc div midway medical co
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
Packagers
Dosage forms
Form Route Strength
Solution Intravenous
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Aminophylline 250 mg/10 ml vial 0.48 USD ml
Aminophylline 25 mg/ml 0.41 USD ml
Phyllocontin-350 350 mg Sustained-Release Tablet 0.31 USD tablet
Aminophylline 100 mg tablet 0.26 USD tablet
Phyllocontin 225 mg Sustained-Release Tablet 0.24 USD tablet
Aminophylline powder 0.17 USD g
Aminophylline 200 mg tablet 0.15 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility 2E+005 mg/L MERCK INDEX (1996)
logP -3.03 Not Available
Predicted Properties
Property Value Source
logP -0.77 ChemAxon
pKa (strongest acidic) 7.82 ChemAxon
pKa (strongest basic) -0.78 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 69.3 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 44.93 ChemAxon
polarizability 16.86 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00227 Link_out
PubChem Compound 9433 Link_out
PubChem Substance 46508784 Link_out
ChemSpider 9062 Link_out
Therapeutic Targets Database DAP000613 Link_out
PharmGKB PA164781029 Link_out
Drug Product Database 582662 Link_out
Drugs.com http://www.drugs.com/cdi/aminophylline.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Aminophylline Link_out
ATC Codes
  • R03DA05
AHFS Codes
  • 86:16.00
PDB Entries Not Available
FDA label Not Available
MSDS show (72.7 KB)
Interactions
Drug Interactions
Drug Interaction
Aciclovir Acyclovir increases the effect and toxicity of theophylline
Adenosine This xanthine decreases the effect of adenosine
Amobarbital The barbiturate, amobarbital, decreases the effect of aminophylline.
Aprobarbital The barbiturate, aprobarbital, decreases the effect of aminophylline.
Atracurium Theophylline decreases the effect of muscle relaxant
Bromazepam Aminophylline may decrease the therapeutic effect of bromazepam. Monitor for changes in the therapeutic effects of bromazepam if aminophylline is initiated, discontinued or dose changed.
Butabarbital The barbiturate, butabarbital, decreases the effect of aminophylline.
Butalbital The barbiturate, butalbital, decreases the effect of aminophylline.
Butethal The barbiturate, butethal, decreases the effect of aminophylline.
Carbamazepine Carbamazepine may decrease the serum concentration of aminophylline. Aminophylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Carteolol Antagonism of action and increased effect of theophylline
Cimetidine Cimetidine may increase the serum concentration of aminophylline by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of aminophylline if cimetidine is initiated, discontinued or dose changed.
Ciprofloxacin Ciprofloxacin may increase the effect of aminophylline.
Clarithromycin Clarithromycin may increase the effect amd toxicity of aminophylline.
Dihydroquinidine barbiturate The barbiturate, dihydroquinidine barbiturate, decreases the effect of aminophylline.
Disulfiram Disulfiram may increase the effect and toxicity of aminophylline.
Doxacurium chloride Theophylline decreases the effect of muscle relaxant
Enoxacin Enoxacin may increase the effect of aminophylline.
Erythromycin The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, aminophylline.
Ethinyl Estradiol The contraceptive increases the effect and toxicity of theophylline
Ethotoin Decreased effect of both products
Fluvoxamine Fluvoxamine may increase the effect and toxicity of aminophylline.
Fosphenytoin Decreased effect of both products
Grepafloxacin Grepafloxacin may increase the effect of aminophylline.
Halothane Increased risk of cardiac arrhythmia
Heptabarbital The barbiturate, heptabarbital, decreases the effect of aminophylline.
Hexobarbital The barbiturate, hexobarbital, decreases the effect of aminophylline.
Interferon Alfa-2a, Recombinant Interferon increases the effect and toxicity of theophylline
Interferon Alfa-2b, Recombinant Interferon increases the effect and toxicity of theophylline
Interferon alfa-n1 Interferon increases the effect and toxicity of theophylline
Isoniazid Isoniazid may increase the effect and toxicity of oxtriphylline.
Josamycin The macrolide, josamycin, may increase the effect and toxicity of the theophylline derivative, aminophylline.
Lithium Theophylline decreases serum levels of lithium
Mephenytoin Decreased effect of both products
Mestranol The contraceptive increases the effect and toxicity of theophylline
Methohexital The barbiturate, methohexital, decreases the effect of aminophylline.
Methylphenobarbital The barbiturate, methylphenobarbital, decreases the effect of aminophylline.
Metocurine Theophylline decreases the effect of muscle relaxant
Mexiletine Mexiletine increases the effect and toxicity of theophylline
Mivacurium Theophylline decreases the effect of muscle relaxant
Nadolol Antagonism of action and increased effect of theophylline
Norfloxacin Norfloxacin may increase the effect of aminophylline.
Pancuronium Theophylline decreases the effect of muscle relaxant
Pefloxacin Pefloxacin may increase the effect of aminophylline.
Peginterferon alfa-2a Interferon increases the effect and toxicity of theophylline
Peginterferon alfa-2b Interferon increases the effect and toxicity of theophylline
Penbutolol Antagonism of action and increased effect of theophylline
Pentobarbital The barbiturate, pentobarbital, decreases the effect of aminophylline.
Pentoxifylline Pentoxifylline may increase the effect and toxicity of aminophylline.
Phenobarbital The barbiturate, phenobarbital, decreases the effect of aminophylline.
Phenytoin Decreased effect of both products
Pindolol Antagonism of action and increased effect of theophylline
Primidone The barbiturate, primidone, decreases the effect of aminophylline.
Propafenone Propafenone increases the effect of theophylline
Propranolol Antagonism of action and increased effect of theophylline
Quinidine barbiturate The barbiturate, quinidine barbiturate, decreases the effect of aminophylline.
Regadenoson Reduces duration of >2-fold increase in peak flow velocity. No effect on heart rate increase.
Rifampin Rifampin decreases the effect of theophylline
Ritonavir Ritonavir decreases the effect of theophylline
Rofecoxib Rofecoxib increases the effect and toxicity of theophylline
Secobarbital The barbiturate, secobarbital, decreases the effect of aminophylline.
Sotalol Antagonism of action and increased effect of theophylline
St. John's Wort St. John's Wort decreases the effect of theophylline
Tacrine Tacrine may reduce the elimination rate of Aminophylline. Monitor for changes in the therapeutic and toxic effects of theophylline if Tacrine is initiated, discontinued or if the dose is changed.
Talbutal The barbiturate, talbutal, decreases the effect of aminophylline.
Temazepam Aminophylline may decrease the efficacy of Temazepam. Monitor for changes in the therapeutic effect of Temazepam if Aminophylline is initiated, discontinued or dose changed.
Terbinafine Terbinafine increases the effect and toxicity of theophylline
Thiabendazole The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Aminophylline by decreasing Aminophylline metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Aminophylline if Thiabendazole is initiated, discontinued or dose changed.
Ticlopidine Ticlopidine increases the effect and toxicity of theophylline
Timolol Antagonism of action and increased effect of theophylline
Troleandomycin The macrolide, troleandomycin, may increase the effect and toxicity of theophylline derivative, aminophylline.
Tubocurarine Theophylline decreases the effect of muscle relaxant
Vecuronium Theophylline decreases the effect of muscle relaxant
Verapamil Verapamil increases the effect of theophylline
Zafirlukast Zafirlukast serum concentrations may be decreased by the theophylline derivative Aminophylline.
Zileuton Zileuton increases the effect and toxicity of theophylline
Food Interactions
  • Limit caffeine intake.
  • Take with food.
  • Vitamin B6 needs increased, supplement recommended.
Targets

1. cGMP-inhibited 3',5'-cyclic phosphodiesterase A

Pharmacological action: yes
Actions: inhibitor

Hydrolyzes both cyclic AMP (cAMP) and cyclic GMP (cGMP)

Organism class: human
UniProt ID: Q14432 Link_out
Gene: PDE3A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hirota K, Yoshioka H, Kabara S, Koizumi Y, Abe H, Sato T, Matsuki A: Spasmolytic effects of colforsin daropate on serotonin-induced pulmonary hypertension and bronchoconstriction in dogs. Acta Anaesthesiol Scand. 2002 Mar;46(3):297-302. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Adenosine A1 receptor

Pharmacological action: yes
Actions: antagonist

Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase

Organism class: human
UniProt ID: P30542 Link_out
Gene: ADORA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamamoto S, Nakanishi O, Matsui T, Shinohara N, Kinoshita H, Lambert C, Ishikawa T: Intrathecal adenosine A1 receptor agonist attenuates hyperalgesia without inhibiting spinal glutamate release in the rat. Cell Mol Neurobiol. 2003 Apr;23(2):175-85. Pubmed
  2. Lerman BB: Response of nonreentrant catecholamine-mediated ventricular tachycardia to endogenous adenosine and acetylcholine. Evidence for myocardial receptor-mediated effects. Circulation. 1993 Feb;87(2):382-90. Pubmed

3. Adenosine A3 receptor

Pharmacological action: yes
Actions: antagonist

Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction

Organism class: human
UniProt ID: P33765 Link_out
Gene: ADORA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Stella L, de Novellis V, Marabese I, Berrino L, Maione S, Filippelli A, Rossi F: The role of A3 adenosine receptors in central regulation of arterial blood pressure. Br J Pharmacol. 1998 Oct;125(3):437-40. Pubmed
Enzymes

1. Cytochrome P450 1A2

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2E1

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:20