Theophyllin

Theophylline Struktur
58-55-9
CAS-Nr.
58-55-9
Bezeichnung:
Theophyllin
Englisch Name:
Theophylline
Synonyma:
Theophyllin;THEOPHYLINE;1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione;3,7-DIHYDRO-1,3-DIMETHYL-1H-PURINE-2,6-DIONE;theo-24;theobid;slo-bid;Theolair;duraphyl;Elixicon
CBNumber:
CB4285388
Summenformel:
C7H8N4O2
Molgewicht:
180.16
MOL-Datei:
58-55-9.mol

Theophyllin Eigenschaften

Schmelzpunkt:
271-273 °C
Siedepunkt:
312.97°C (rough estimate)
Dichte
1.3640 (rough estimate)
Brechungsindex
1.6700 (estimate)
Flammpunkt:
11 °C
storage temp. 
2-8°C
Löslichkeit
0.1 M HCl: soluble
Aggregatzustand
powder
pka
8.77(at 25℃)
Farbe
white
Wasserlöslichkeit
8.3 g/L (20 ºC)
Merck 
14,9285
BRN 
13463
BCS Class
3,1
Stabilität:
Stable. Incompatible with strong oxidizing agents.
InChIKey
ZFXYFBGIUFBOJW-UHFFFAOYSA-N
LogP
-0.020
CAS Datenbank
58-55-9(CAS DataBase Reference)
IARC
3 (Vol. 51) 1991
NIST chemische Informationen
1,3-Dimethylxanthine(58-55-9)
EPA chemische Informationen
Theophylline (58-55-9)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,T,F,Xi
R-Sätze: 22-39/23/24/25-23/24/25-11-36/37/38
S-Sätze: 7-16-36/37-45-36-26-24/25
RIDADR  UN 2811 6.1/PG 3
WGK Germany  1
RTECS-Nr. XH3850000
10-23
TSCA  Yes
HazardClass  6.1(b)
PackingGroup  III
HS Code  29395900
Giftige Stoffe Daten 58-55-9(Hazardous Substances Data)
Toxizität LD50 oral in rabbit: 350mg/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Theophyllin Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD

WEISSES KRISTALLINES PULVER

CHEMISCHE GEFAHREN

Die Substanz zersetzt sich beim Erhitzen unter Bildung von giftigen Rauchen mit Stickoxiden.

ARBEITSPLATZGRENZWERTE

TLV nicht festgelegt.
MAK nicht festgelegt.

AUFNAHMEWEGE

Aufnahme in den Körper in gefährlichen Mengen durch Verschlucken.

INHALATIONSGEFAHREN

Eine belästigende Partikelkonzentration in der Luft kann schnell erreicht werden durch Dispergieren.

WIRKUNGEN BEI KURZZEITEXPOSITION

WIRKUNGEN BEI KURZZEITEXPOSITION:
Möglich sind Auswirkungen auf das Herz und das Zentralnervensystem mit Herzrhythmusstörungen und Krämpfen. Die Auswirkungen treten u.U. verzögert ein.

LECKAGE

Persönliche Schutzausrüstung: Atemschutzgerät mit Partikelfilter entsprechend der Arbeitsplatzkonzentration des Stoffes. Verschüttetes Material in abdichtbaren Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. An sicheren Ort bringen.

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S7:Behälter dicht geschlossen halten.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Beschreibung

Theophylline is a methylxanthine that acts as a weak bronchodilator. It is useful for chronic therapy and is not helpful in acute exacerbations.
Theophylline is a methylxanthine alkaloid that is a competitive inhibitor of phosphodiesterase (PDE; Ki = 100 μM). It is also a non-selective antagonist of adenosine A receptors (Ki = 14 μM for A1 and A2). Theophylline induces relaxation of feline bronchiole smooth muscle precontracted with acetylcholine (EC40 = 117 μM; EC80 = 208 μM). Formulations containing theophylline have been used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Chemische Eigenschaften

white to light yellow crystal powder

Physikalische Eigenschaften

Appearance: white, crystalline powder, odorless, with a bitter taste. Solubility: freely soluble in solutions of alkali hydroxides and in ammonia; sparingly soluble in alcohol, in chloroform, and in ether; slightly soluble in water. Water solubility, 7.36?g/L (20?°C); density, 1.62?g/cm3 ; melting point, 270–274?°C; boiling point, 390.1?°C (760? mmHg); flash point, 189.7?°C; vapor pressure, 2.72E-06? mmHg (25?°C).

Verwenden

theophylline is tonic and skin conditioning. Its cosmetic activity is not clearly or definitively established. It is most often found in anti-cellulite products. Theophylline is in the same family of bio chemicals as caffeine. It is naturally occurring in tea.

Definition

ChEBI: Theophylline is a dimethylxanthine having the two methyl groups located at positions 1 and 3. It is structurally similar to caffeine and is found in green and black tea. It has a role as a vasodilator agent, a bronchodilator agent, a muscle relaxant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an anti-asthmatic drug, an anti-inflammatory agent, an immunomodulator, an adenosine receptor antagonist, a drug metabolite, a fungal metabolite and a human blood serum metabolite.

Indications

Twenty years ago theophylline (Theo-Dur, Slo-bid, Uniphyl, Theo-24) and its more soluble ethylenediamine salt, aminophylline, were the bronchodilators of choice in the United States. Although the β2-adrenoceptor agonists now fill this primary role, theophylline continues to have an important place in the therapy of asthma because it appears to have antiinflammatory as well as bronchodilator activity.

Allgemeine Beschreibung

Odorless white crystalline powder. Odorless. Bitter taste.

Air & Water Reaktionen

Slightly soluble in water.

Reaktivität anzeigen

Theophylline neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Hazard

Questionable carcinogen.

Brandgefahr

Flash point data for Theophylline are not available, however Theophylline is probably combustible.

Biologische Aktivität

Bronchodilator, anti-inflammatory and immunomodulator. Antagonizes adenosine receptors and is a weak non-selective inhibitor of phosphodiesterases (PDEs).

Mechanism of action

In spite of a great deal of investigation, just how theophylline causes bronchodilation is not clearly understood. Inhibition of the enzyme PDE, which is responsible for the hydrolysis of cAMP and cyclic guanosine monophosphate (cGMP), generally is put forth as the mechanism of action; however, theophylline also is an adenosine antagonist and has been implicated in stimulation of the release of catecholamines. It has been clearly shown that theophylline does inhibit PDEs in vitro, and x-ray crystallographic studies have identified the binding residues that interact with the methylxanthines. Theophylline binds to a subpocket of the active site and appears to be sandwiched between a phenylalanine and a valine via hydrophobic bonds. Its binding affinity is reinforced by hydrogenbonding between a tyrosine and N-7 and a glutamine and O-6 of the xanthine ring system. There are more than 11 families of PDEs, and studies have shown that theophylline binds in a similar manner to both the PDE4 and PDE5 family isoforms.

Pharmakologie

Smooth muscle relaxation, central nervous system (CNS) excitation, and cardiac stimulation are the principal pharmacological effects observed in patients treated with theophylline.The action of theophylline on the respiratory system is easily seen in the asthmatic by the resolution of obstruction and improvement in pulmonary function. Other mechanisms that may contribute to the action of theophylline in asthma include antagonism of adenosine, inhibition of mediator release, increased sympathetic activity, alteration in immune cell function, and reduction in respiratory muscle fatigue. Theophylline also may exert an antiinflammatory effect through its ability to modulate inflammatory mediator release and immune cell function.
Inhibition of cyclic nucleotide phosphodiesterases is widely accepted as the predominant mechanism by which theophylline produces bronchodilation. Phosphodiesterases are enzymes that inactivate cAMP and cyclic guanosine monophosphate (GMP), second messengers that mediate bronchial smooth muscle relaxation.

Clinical Use

The principal use of theophylline is in the management of asthma. It is also used to treat the reversible component of airway obstruction associated with chronic obstructive pulmonary disease and to relieve dyspnea associated with pulmonary edema that develops from congestive heart failure.

Nebenwirkungen

Theophylline has a narrow therapeutic index and produces side effects that can be severe, even life threatening. Importantly, the plasma concentration of theophylline cannot be predicted reliably from the dose. In one study, the oral dosage of theophylline required to produce therapeutic plasma levels (i.e., between 10 and 20 μg/mL) varied between 400 and 3,200 mg/day. Heterogeneity among individuals in the rate at which they metabolize theophylline appears to be the principal factor responsible for the variability in plasma levels. Such conditions as heart failure, liver disease, and severe respiratory obstruction will slow the metabolism of theophylline.

Sicherheitsprofil

Human poison by ingestion, parenteral, intravenous, and rectal routes. Experimental poison by multiple routes. An experimental teratogen. Human systemic effects: coma, convulsions or effect on seizure threshold, cyanosis, EKG changes, fever and other metabolic effects, heart arrhythmias, heart rate change, hyperglycemia, metabolic acidosis, nausea or vomiting, potassium-level changes, respiratory stimulation, salivary gland changes, somnolence, tremor. Experimental reproductive effects. Human mutation data reported. Used as a dturetic, cardtac stimulant, smooth muscle relaxant, and to treat asthma. When heated to decomposition it emits toxic fumes of NOx.

Environmental Fate

Theophylline is readily broken down in the environment. It may undergo photolytic degradation in the air or when exposed to light. In moist soil, or aqueous environments, it undergoes rapid biodegradation.

Stoffwechsel

Chemically, theophylline is 1,3-dimethylxanthine and contains both an acidic and a basic nitrogen (N-7 and N-9, respectively). Physiologically, it behaves as an acid (pKa = 8.6), and its poor aqueous solubility can be enhanced by salt formation with organic bases. Theophylline is metabolized by a combination of C-8 oxidation and N-demethylation to yield methyluric acid metabolites. The major urinary metabolite is 1,3-dimethyl uric acid, which is the product of the action of xanthine oxidase. Because none of the metabolites is uric acid itself, theophylline can be safely given to patients who suffer from gout.

läuterung methode

It crystallises from H2O as the monohydrate which becomes anhydrous above 100o. It is freely soluble in hot H2O, but its solubility at 15o is 0.44%. It complexes with heavy metals. It is a diuretic, vasodilator and a cardiac stimulant. [Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp253-254 1971, ISBN 0-471-38205-1, Beilstein 26 H 455, 26 I 134, 26 II 263, 26 III/IV 2331.]

Vorsichtsmaßnahmen

Theophylline should be used with caution in patientswith myocardial disease, liver disease, and acutemyocardial infarction. The half-life of theophylline isprolonged in patients with congestive heart failure.Because of its narrow margin of safety, extreme cautionis warranted when coadministering drugs, such as cimetidineor zileuton, that may interfere with the metabolismof theophylline. Indeed, coadministration of zileutonwith theophylline is contraindicated. It is alsoprudent to be careful when using theophylline in patientswith a history of seizures.

Einzelnachweise

Fischer., Ber., 30, 553 (1897)
Schwabe., Arch. Pharm., 245, 312 (1907)
Biltz, Strufe.,Annalen, 404, 137, 170(1914)
Yoshitomi., Chem. Abstr., 19,2303 (1925)
Mossini., Boll. chim. farm., 75, 557 (1936)
Deichmeister., Farm. Zhur., 13, 18 (1940)
Deichmeister., Chem. Zentr., 1, 1280 (1942)
Deniges., Bull. trav. soc. ph arm. Bordeaux, 79, 141 (1941)
Lesser., Drug & Cosmetic Ind., 66, 276,340 (1950)

Theophyllin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Theophyllin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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58-55-9(Theophyllin)Verwandte Suche:


  • Theocontin
  • Theodel
  • Theo-dur
  • theo-dur-sprinkle
  • Theofol
  • Theograd
  • Theolix
  • Theona P
  • Theophyl-225
  • Theophylline, anhydrous
  • theosine
  • THEOPHYLLINE,ANHYDROUS,USP
  • THEOPHYLLINE(SH)
  • THEOPHYLLINE(USP)(P)
  • THEOPHYLLINE[1,3-DIMETHYL-2,6-DIOXO-1,2,3,6-TETRAHYDROPURINE]
  • Theophylline (base and/or unspecified salts)
  • Theophylline solution
  • Theophyline anhydrous (B.P)
  • THEOPHYLLINE METHANOL SOLUTION
  • 1,3-Dimethylxanthine, 2,6-Dihydroxy-1,3-dimethylpurine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione
  • Theotard
  • Theophylline,99+%,anhydrous
  • 1,3-Dimethylxanthine
  • Theophylline,1,3-Dimethylxanthine, 2,6-Dihydroxy-1,3-dimethylpurine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione
  • Theophylline (200 mg)
  • Theophylline (200 mg) Certified Reference Material (CRM)
  • Theophylline Extended-Release Beads (Drug Release Calibrator, Multiple Unit) (20 g) DIS-CONTINUED
  • 1,3-DiMethyl-2,6-dihyroxypurine
  • component of Quibron-t/sr
  • component of Slo-phyllin gg
  • component of Theolair plus
  • component of Theo-organdin
  • component of Theo-Organidin
  • constant-t
  • Doraphyllin
  • duraphy
  • Dyspne-Inhal
  • Elixex
  • euphylong
  • GS 2591A
  • Liquophylline
  • liquoplylline
  • Maphylline
  • Medaphyllin
  • NSC 2066
  • somophyllin-t
  • spophyllinretard
  • Synophylate-L.A. Cenules
  • Teofilina
  • Teofyllamin
  • Teolair
  • Theacitin
  • Theal tabl.
  • thealtablets
  • Theo-11
  • theophylline,anhydrous
  • theostat80
  • unidur
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