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T1633 Sigma

Theophylline

anhydrous, ≥99%, powder

Synonym: 1,3-Dimethylxanthine, 2,6-Dihydroxy-1,3-dimethylpurine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
grade   anhydrous
assay   ≥99%
form   powder
color   white
solubility   H2O: slightly soluble8.3 mg/ml
  NH4OH: soluble50 mg/ml, clear, colorless
  alcohol: soluble12.5 mg/ml
  chloroform: soluble9.1 mg/ml
  0.1 M HCl: soluble
  0.1 M NaOH: soluble
  ammonium hydroxide: soluble
  aqueous base: soluble
  diethyl ether: slightly soluble
  dilute HCl: soluble
  dilute nitric acid: soluble
  ethanol: moderately soluble
originator   Forest Labs
Gene Information   human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE3A(5139), PDE4B(5142)
mouse ... Adora2b(11541)
rat ... Adora1(29290), Adora2a(25369), Adora2b(29316), Pde1b(29691), Pde3a(50678)

Description

Biochem/physiol Actions

Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication.

Theophylline is a tea alkaloid that functions as a nonselective PDE4 inhibitor. It can induce smooth muscle relaxation in the bronchiolae of asthma patients. At increased concentrations, theophylline can function as a reprotoxic agent and can cause infertility by incapacitating Sertoli cells. This subsequently causes the premature release of late differentiating spermatogenic cells1.

Packaging

1 kg in poly bottle

50, 100, 250 g in poly bottle

Preparation Note

Theophylline dissolves in 1 M NH4OH at 50 mg/ml to yield a clear, colorless solution. It is soluble in 0.1 M HCl, 0.1 M NaOH and is slightly soluble(8.3 mg/ml) in water. It is also moderately soluble in ethanol. Furthermore, it is soluble in alcohol (12.5 mg/ml), and chloroform (9.1 mg/ml), alkali hydroxides, ammonia, dilute hydrochloric or nitric acid, but is sparingly soluble in ether.

The solubility of the methylxanthines is low, but can be enhanced by the formation of complexes (usually 1:1) with a wide variety of compounds such as ethylenediamine (to form aminophylline). The formation of complex double salts (caffeine and sodium benzoate) or true salts (like choline theophyllinate, and oxtriphylline) also improves aqueous solubility. These salts or complexes dissociate to yield the parent methylxanthines when dissolved in biological fluids and should not be confused with covalently modified derivatives such asdyphylline (1,3-dimethyl-7-(2,3-dihydroxypropyl)-xanthine).

Application

Theophylline has been used to study its effects on rat gene expression in the ubiquitin-proteasome pathway that regulates spermatogenesis and epididymal sperm quality1. Theophylline has also been used as an internal standard for the measurement of plasma paracetamol levels in humans2.

Features and Benefits

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the Adenosine Receptors and Phosphodiesterases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Forest Labs. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
22
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
1
RTECS 
XH3850000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

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Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

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Transmission of an extracellular signal across the cell membrane is initiated by activation of many types of hormone and neurotransmitter receptors, such as G-protein coupled receptors (GPCRs), and c...
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Peer-Reviewed Papers

References

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2. Bioavailability of two new formulations of paracetamol, compared with three marketed formulations, in healthy volunteers. Sevilla-Tirado FJ, González-Vallejo EB, Leary AC, et al. Methods Find. Exp. Clin. Pharmacol. 25(7), 531-5, (2003)

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Mutagenic and genotoxic effects of theophylline and theobromine in Salmonella assay and in vivo sister chromatid exchanges in bone marrow cells of mice. Giri, et al. Mutat. Res. 444, 17-23, (1999)

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Theophylline for prevention of contrast-induced nephropathy: a systematic review and meta-analysis. Bagshaw SM and Ghali WA Arch. Intern. Med. 165(10), 1087-93, (2005)

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Efficacy of theophylline in people with stable chronic obstructive pulmonary disease: a systematic review and meta-analysis. Ram FS, Jardin JR, Atallah A, et al. Respir. Med. 99(2), 135-44, (2005)

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Effects of andrographolide on the pharmacokinetics of aminophylline and doxofylline in rats. Li XP, Zhang CL, Gao P, et al. Drug Res. (Stuttg.) 63(5), 258-62, (2013)

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Simultaneous in vivo phenotyping of CYP enzymes. Ghassabian S and Murray M Methods Mol. Biol. 987, 261-7, (2013)

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[Theophylline, a new look to an old drug]. Morfín Maciel BM and Castillo Morfín BM Rev. Alerg. Mex. 57(4), 112-22, (2010)

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[The pathogenesis of chronic obstructive pulmonary disease, steroid resistance and the place of theophylline in the treatment]. Bayram H Tuberk. Toraks 57(1), 115-24, (2009)

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Effect of theophylline associated with short-acting or long-acting inhaled beta2-agonists in patients with stable chronic obstructive pulmonary disease: a systematic review. Zacarias EC, Castro AA, and Cendon S J. Bras. Pneumol. 33(2), 152-60, (2007)

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Hologram QSAR model for the prediction of human oral bioavailability. Tiago L Moda et al Bioorg. Med. Chem. 15, 7738-45, (2007)

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Biophysical mapping of the adenosine A2A receptor. Andrei Zhukov et al J. Med. Chem. 54, 4312-23, (2011)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease. Arumugam Kodimuthali et al J. Med. Chem. 51, 5471-89, (2008)

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Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk). Giulia Caron et al J. Med. Chem. 48, 3269-79, (2005)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Guarana powder polysaccharides: characterisation and evaluation of the antioxidant activity of a pectic fraction. Dalonso N and Petkowicz CL Food Chem. 134(4), 1804-12, (2012)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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Pyrido[2,3-e]-1,2,4-triazolo[4,3-a]pyrazin-1-one as a new scaffold to develop potent and selective human A3 adenosine receptor antagonists. Synthesis, pharmacological evaluation, and ligand-receptor modeling studies. Vittoria Colotta et al J. Med. Chem. 52, 2407-19, (2009)

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Cyclic AMP can promote APL progression and protect myeloid leukemia cells against anthracycline-induced apoptosis. Gausdal G, Wergeland A, Skavland J, et al. Cell Death Dis. 4, e516, (2013)

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Are phosphodiesterase 4 inhibitors just more theophylline? Boswell-Smith V, Cazzola M, and Page CP J. Allergy Clin. Immunol. 117(6), 1237-43, (2006)

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Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species. Francisco J Prado-Prado et al Bioorg. Med. Chem. 18, 2225-31, (2010)

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Effect of theophylline on prevention of contrast-induced acute kidney injury: a meta-analysis of randomized controlled trials. Dai B, Liu Y, Fu L, et al. Am. J. Kidney Dis. 60(3), 360-70, (2012)

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The influence of agitation sequence and ionic strength on in vitro drug release from hypromellose (E4M and K4M) ER matrices--the use of the USP III apparatus. Asare-Addo K, Kaialy W, Levina M, et al. Colloids Surf. B Biointerfaces 104, 54-60, (2013)

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Simultaneous quantification of caffeine and its three primary metabolites in rat plasma by liquid chromatography-tandem mass spectrometry. Choi EJ, Bae SH, Park JB, et al. Food Chem. 141(3), 2735-42, (2013)

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Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain. Lei Du-Cuny et al Bioorg. Med. Chem. 17, 6983-92, (2009)

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Prevention of contrast nephropathy in critically ill patients using acetylcysteine and theophylline. Mueller C Int. J. Artif. Organs 27(12), 1066-9, (2004)

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Determination of permeability and lipophilicity of pyrazolo-pyrimidine tyrosine kinase inhibitors and correlation with biological data. Elena Dreassi et al Eur. J. Med. Chem. 44, 3712-7, (2009)

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Predicting drug release from HPMC/lactose tablets. Siepmann J, Karrout Y, Gehrke M, et al. Int. J. Pharm. 441(1-2), 826-34, (2013)

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Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP). Shyama Sidique et al Bioorg. Med. Chem. Lett. 19, 222-5, (2009)

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Melanogenesis of methyl myristate loaded niosomes in B16F10 melanoma cells. Manosroi A, Chaikul P, Abe M, et al. J. Biomed. Nanotechnol. 9(4), 626-38, (2013)

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Chronological effects of rifampicin discontinuation on cytochrome P450 activity in healthy Japanese volunteers, using the cocktail method. Inui N, Akamatsu T, Uchida S, et al. Clin. Pharmacol. Ther. 94(6), 702-8, (2013)

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Multiple dosing of ephedra-free dietary supplements: hemodynamic, electrocardiographic, and bacterial contamination effects. Foster L, Allan MC, Khan A, et al. Clin. Pharmacol. Ther. 93(3), 267-74, (2013)

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Binding thermodynamics as a tool to investigate the mechanisms of drug-receptor interactions: thermodynamics of cytoplasmic steroid/nuclear receptors in comparison with membrane receptors. Paola Gilli et al J. Med. Chem. 48, 2026-35, (2005)

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Development and validation of a stability indicating assay of doxofylline by RP-HPLC: ESI-MS/MS, ¹H and ¹³C NMR spectroscopic characterization of degradation products and process related impurities. Rao RN, Naidu ChG, Prasad KG, et al. J. Pharm. Biomed. Anal. 78-79, 92-9, (2013)

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First-principle, structure-based prediction of hepatic metabolic clearance values in human. Haiyan Li et al Eur. J. Med. Chem. 44, 1600-6, (2009)

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Endocrine regulation of airway contractility is overlooked. Bossé Y J. Endocrinol. 222(2), R61-73, (2014)

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Neural computational prediction of oral drug absorption based on CODES 2D descriptors. A Guerra et al Eur. J. Med. Chem. 45, 930-40, (2010)

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QSAR-based permeability model for drug-like compounds. Rafael Gozalbes et al Bioorg. Med. Chem. 19, 2615-24, (2011)

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Design and synthesis of selective inhibitors of placental alkaline phosphatase. Lanier, M., et al. Bioorg. Med. Chem. 18, 573-9, (2010)

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Theophylline cocrystals prepared by spray drying: physicochemical properties and aerosolization performance. Alhalaweh A, Kaialy W, Buckton G, et al. AAPS PharmSciTech 14(1), 265-76, (2013)

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Inhibition of CTP synthase from Escherichia coli by xanthines and uric acids. Alexander C Roy et al Bioorg. Med. Chem. Lett. 20, 141-4, (2010)

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Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. Xiaofan Sui et al Eur. J. Med. Chem. 44, 4455-60, (2009)

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Long-acting beta2-agonists versus theophylline for maintenance treatment of asthma. Tee AK, Koh MS, Gibson PG, et al. Cochrane Database Syst. Rev. (3), CD001281, (2007)

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Glycopyrrolate and theophylline for the treatment of severe pallid breath-holding spells. Carano N, Bo I, Zanetti E, et al. Pediatrics 131(4), e1280-3, (2013)

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Impaired mutagenic activities of MPDP(+) (1-methyl-4-phenyl-2,3-dihydropyridinium) and MPP(+) (1-methyl-4-phenylpyridinium) due to their interactions with methylxanthines. Katarzyna Ulanowska et al Bioorg. Med. Chem. 15, 5150-7, (2007)

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Synthesis, hydrolyses and dermal delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) derivatives of phenol, imide and thiol containing drugs. Susruta Majumdar et al Bioorg. Med. Chem. Lett. 16, 3590-4, (2006)

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Theophylline therapy for Cheyne-Stokes respiration during sleep in a 41-year-old man with refractory arterial hypertension. Wolf J, Swierblewska E, Jasiel-Wojculewicz H, et al. Chest 146(1), e8-e10, (2014)

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Streptavidin binding bifunctional aptamers and their interaction with low molecular weight ligands. Le TT, Scott S, and Cass AE Anal. Chim. Acta 761, 143-8, (2013)

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Determination of ambroxol hydrochloride, guaifenesin, and theophylline in ternary mixtures and in the presence of excipients in different pharmaceutical dosage forms. Abdelwahab NS J. AOAC Int. 95(6), 1629-38, (2012)

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Development of a validated LC-MS/MS method for determination of doxofylline on rat dried blood spots and urine: application to pharmacokinetics. Rao RN, Prasad KG, Naidu ChG, et al. J. Pharm. Biomed. Anal. 78-79, 211-6, (2013)

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Spectroscopic investigations and hydrogen bond interactions of 8-aza analogues of xanthine, theophylline and caffeine: a theoretical study. Karthika M, Kanakaraju R, and Senthilkumar L J. Mol. Model. 19(4), 1835-51, (2013)

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Hydrophilic modification of silicone elastomer films: thermal, mechanical and theophylline permeability properties. Soulas DN, Sanopoulou M, and Papadokostaki KG Mater. Sci. Eng. C. Mater. Biol. Appl. 33(4), 2122-30, (2013)

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Synthesis of theophylline derivatives and study of their activity as antagonists at adenosine receptors J. Hierrezuelo, et al. Bioorg. Med. Chem. 18, 2081-2088, (2010)

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Use of theophylline in chronic obstructive pulmonary disease: examining the evidence. Ram FS Curr. Opin. Pulm. Med. 12(2), 132-9, (2006)

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Comparison of ionic and non-ionic drug release from multi-membrane spherical aerogels. Veronovski A, Knez Z, and Novak Z Int. J. Pharm. 454(1), 58-66, (2013)

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Design of sustained release fine particles using two-step mechanical powder processing: particle shape modification of drug crystals and dry particle coating with polymer nanoparticle agglomerate. Kondo K, Ito N, Niwa T, et al. Int. J. Pharm. 453(2), 523-32, (2013)

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Formulation parameters and release mechanism of theophylline loaded ethyl cellulose microspheres: effect of different dual surfactant ratios. Thakare M, Israel B, Garner ST, et al. Pharm. Dev. Technol. 18(5), 1213-9, (2013)

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Effects of caffeine and theophylline on coronary hyperemia induced by adenosine or dipyridamole. Salcedo J and Kern MJ Catheter. Cardiovasc. Interv. 74(4), 598-605, (2009)

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Can β2-adrenoceptor agonists, anticholinergic drugs, and theophylline contribute to the control of pulmonary inflammation and emphysema in COPD? Zhang WH, Zhang Y, Cui YY, et al. Fundam. Clin. Pharmacol. 26(1), 118-34, (2012)

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Dihydroxy-pyrimidine and N-methylpyrimidone HIV-integrase inhibitors: improving cell based activity by the quaternarization of a chiral center. Emanuela Nizi et al Bioorg. Med. Chem. Lett. 19, 4617-21, (2009)

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Synthesis of selective SRPK-1 inhibitors: novel tricyclic quinoxaline derivatives. Zsolt Székelyhidi et al Bioorg. Med. Chem. Lett. 15, 3241-6, (2005)

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Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Lee SY, Jang H, Lee JY, et al. Toxicol. Lett. 229(1), 33-40, (2014)

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First-line therapy for theophylline-associated seizures. Yoshikawa H Acta Neurol. Scand 115(4 Suppl), 57-61, (2007)

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Comparative study of the interactions between ovalbumin and three alkaloids by spectrofluorimetry. Wang RQ, Yin YJ, Li H, et al. Mol. Biol. Rep. 40(4), 3409-18, (2013)

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Second pathways in the pathophysiology of ischemic priapism and treatment alternatives. Karakeci A, Firdolas F, Ozan T, et al. Urology 82(3), 625-9, (2013)

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Efficacy of theophylline plus salmeterol/fluticasone propionate combination therapy in patients with asthma. Nie H, Zhang G, Liu M, et al. Respir. Med. 107(3), 347-54, (2013)

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N,N'-Dialkylaminoalkylcarbonyl (DAAC) prodrugs and aminoalkylcarbonyl (AAC) prodrugs of 4-hydroxyacetanilide and naltrexone with improved skin permeation properties. H Devarajan-Ketha et al Bioorg. Med. Chem. Lett. 21, 4078-82, (2011)

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Use of methylxanthine therapies for the treatment and prevention of apnea of prematurity. Schoen K, Yu T, Stockmann C, et al. Paediatr. Drugs 16(2), 169-77, (2014)

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Vulnerability of patients with chronic obstructive pulmonary disease according to gender in China. Lou P, Zhu Y, Chen P, et al. Int. J. Chron. Obstruct. Pulmon. Dis. 7, 825-32, (2012)

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Study of doxofylline and its degradation products in bulk drug by a newly developed stability-indicating HPLC method. Patil PS, Hamrapurkar PD, Phale MD, et al. J. AOAC Int. 96(4), 765-70, (2013)

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Influence of ethanol on swelling and release behaviors of Carbopol(®)-based tablets. Rahim SA, Al-Ghazawi M, and Al-Zoubi N Pharm. Dev. Technol. 18(5), 1089-100, (2013)

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Comparison of dissolution profiles of theophylline extended-release dosage forms. Wolny D, Gruchlik A, Chodurek E, et al. Acta Pol. Pharm. 69(6), 1384-6, (2012)

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Merck 14,9285

Beil. 26,IV,2331

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