Posted inUncategorized

Oxtriphylline

July 24, 2017
Common Name

Oxtriphylline Description

Oxtriphylline is a cough medicine derived from xanthine and similar to theophylline, that acts as a bronchodilator to open up airways in the lung. It antagonizes adenosine receptors and promotes relaxation of airway smooth muscles. It is also thought to inhibit phosphodiesterases leading to higher levels of cAMP and increased bronchodilation. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source Choline theophyllinateKegg Choline theophyllineKegg Theophyline – choline mixtKegg TheocolinKegg Choline theophyllinic acidGenerator

Chemical Formlia

C12H21N5O3 Average Molecliar Weight

283.3268 Monoisotopic Molecliar Weight

283.164439563 IUPAC Name

(2-hydroxyethyl)trimethylazanium; 1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-ide Traditional Name

1,3-dimethyl-2,6-dioxo-7H-purin-7-ide; choline CAS Registry Number

4499-40-5 SMILES

C[N+](C)(C)CCO.CN1C2=C([N-]C=N2)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C7H8N4O2.C5H14NO/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;1-6(2,3)4-5-7/h3H,1-2H3,(H,8,9,12);7H,4-5H2,1-3H3/q;+1/p-1

InChI Key

RLANKEDHRWMNRO-UHFFFAOYSA-M Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Imidazopyrimidines Direct Parent

Xanthines Alternative Parents

  • 6-oxopurines
  • Alkaloids and derivatives
  • Pyrimidones
  • Cholines
  • Vinylogous amides
  • Tetraalkylammonium salts
  • Imidazoles
  • Heteroaromatic compounds
  • Ureas
  • 1,2-aminoalcohols
  • Lactams
  • Azacyclic compounds
  • Hydrocarbon derivatives
  • Organic oxides
  • Organic salts
  • Organic zwitterions
  • Organopnictogen compounds
  • Primary alcohols

    • Substituents

  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Choline
  • Pyrimidone
  • Pyrimidine
  • Heteroaromatic compound
  • Tetraalkylammonium salt
  • Vinylogous amide
  • Azole
  • Quaternary ammonium salt
  • Imidazole
  • 1,2-aminoalcohol
  • Urea
  • Lactam
  • Azacycle
  • Alkanolamine
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic zwitterion
  • Amine
  • Organic salt
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Not Available External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Bronchodilator Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility3.84e+00 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility3.84 mg/mLALOGPS logP-0.99ALOGPS logP-0.77ChemAxon logS-1.9ALOGPS pKa (Strongest Acidic)7.82ChemAxon pKa (Strongest Basic)-0.78ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area66.4 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity45.51 m3·mol-1ChemAxon Polarizability16.49 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01303

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01303

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01303 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    25044543 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Oxtriphylline NuGOwiki Link

    HMDB15415 Metagene Link

    HMDB15415 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    774385

    Product: UK 14,305

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in catalytic activity
    Specific function:
    Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (By similarity).
    Gene Name:
    PDE3A
    Uniprot ID:
    Q14432
    Molecular weight:
    124978.06
    References
    1. Rickards KJ, Andrews MJ, Waterworth TH, Alexander GB, Cunningham FM: Differential effects of phosphodiesterase inhibitors on platelet activating factor (PAF)- and adenosine diphosphate (ADP)-induced equine platelet aggregation. J Vet Pharmacol Ther. 2003 Aug;26(4):277-82. [PubMed:12887610 ]
    2. Wu BN, Lin RJ, Lo YC, Shen KP, Wang CC, Lin YT, Chen IJ: KMUP-1, a xanthine derivative, induces relaxation of guinea-pig isolated trachea: the role of the epithelium, cyclic nucleotides and K+ channels. Br J Pharmacol. 2004 Aug;142(7):1105-14. Epub 2004 Jul 5. [PubMed:15237094 ]
    3. Kajikawa S, Kigami D, Nakayama H, Doi K: Changes in submaxillary gland gene expression in F344 rats by multiple dosing of theophylline. Exp Anim. 2006 Apr;55(2):143-6. [PubMed:16651698 ]
    General function:
    Involved in 3,5-cyclic-nucleotide phosphodiesterase activity
    Specific function:
    Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
    Gene Name:
    PDE4A
    Uniprot ID:
    P27815
    Molecular weight:
    98142.155
    References
    1. Wang K, Chen JQ, Chen Z, Chen JC: Inhibition of human phosphodiesterase 4A expressed in yeast cell GL62 by theophylline, rolipram, and acetamide-45. Acta Pharmacol Sin. 2002 Nov;23(11):1013-7. [PubMed:12421478 ]
    2. Haider S: Cyclic AMP level and phosphodiesterase activity during 17alpha,20beta-dihydroxy-4-pregnen-3-one induction and theophylline inhibition of oocyte maturation in the catfish, Clarias batrachus. Comp Biochem Physiol A Mol Integr Physiol. 2003 Feb;134(2):267-74. [PubMed:12547256 ]
    3. Rickards KJ, Andrews MJ, Waterworth TH, Alexander GB, Cunningham FM: Differential effects of phosphodiesterase inhibitors on platelet activating factor (PAF)- and adenosine diphosphate (ADP)-induced equine platelet aggregation. J Vet Pharmacol Ther. 2003 Aug;26(4):277-82. [PubMed:12887610 ]
    4. Usta C, Sadan G, Tuncel B: The effect of the indomethacin on phosphodiesterase inhibitors mediated responses in isolated trachea preparations. Prostaglandins Leukot Essent Fatty Acids. 2004 Sep;71(3):137-41. [PubMed:15253881 ]
    5. Lee JM, Zemans RL, Hejazi M, Chin BB, Ladenson PW, Caturegli P: Modulation of thyroidal radioiodine uptake by theophylline. Exp Mol Pathol. 2004 Oct;77(2):116-20. [PubMed:15351234 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    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. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
    Gene Name:
    CYP1A2
    Uniprot ID:
    P05177
    Molecular weight:
    58406.915
    References
    1. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [PubMed:8846619 ]
    2. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
    3. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    4. Sarkar MA, Hunt C, Guzelian PS, Karnes HT: Characterization of human liver cytochromes P-450 involved in theophylline metabolism. Drug Metab Dispos. 1992 Jan-Feb;20(1):31-7. [PubMed:1346993 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
    Gene Name:
    ADORA1
    Uniprot ID:
    P30542
    Molecular weight:
    36511.3
    References
    1. Nantwi KD, Basura GJ, Goshgarian HG: Adenosine A1 receptor mRNA expression and the effects of systemic theophylline administration on respiratory function 4 months after C2 hemisection. J Spinal Cord Med. 2003 Winter;26(4):364-71. [PubMed:14992338 ]
    2. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
    Gene Name:
    ADORA2A
    Uniprot ID:
    P29274
    Molecular weight:
    44706.9
    References
    1. Pechlivanova DM, Georgiev VP: Effects of single and long-term theophylline treatment on the threshold of mechanical nociception: contribution of adenosine A1 and alpha2-adrenoceptors. Methods Find Exp Clin Pharmacol. 2005 Nov;27(9):659-64. [PubMed:16357952 ]
    2. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607 ]

    Transporters

    General function:
    Involved in transmembrane transport
    Specific function:
    Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
    Gene Name:
    SLC22A7
    Uniprot ID:
    Q9Y694
    Molecular weight:
    60025.0
    References
    1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. [PubMed:15708966 ]

    PMID: 24850427

    Last updated on