(S)-(+)-Ibuprofen Struktur

(S)-(+)-Ibuprofen

Bezeichnung:(S)-(+)-Ibuprofen

CAS-Nr51146-56-6

Englisch Name:(S)-(+)-Ibuprofen

CBNumberCB0699655

SummenformelC13H18O2

Molgewicht206.28

MOL-Datei51146-56-6.mol

(S)-(+)-Ibuprofen physikalisch-chemischer Eigenschaften

Schmelzpunkt	49-53 °C(lit.)
alpha	57 º (c=2, EtOH)
Siedepunkt	285.14°C (rough estimate)
Dichte	1.0364 (rough estimate)
Brechungsindex	59 ° (C=2, EtOH)
Flammpunkt	>230 °F
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
pka	4.41±0.10(Predicted)
Aggregatzustand	solid
Farbe	white
Optische Aktivität	[α]20/D +59°, c = 2 in ethanol
Wasserlöslichkeit	insoluble
BRN	3590022
Stabilität	Stable. Incompatible with strong oxidizing agents.
InChIKey	HEFNNWSXXWATRW-JTQLQIEISA-N
CAS Datenbank	51146-56-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	63-22
S-Sätze:	45-36/37
WGK Germany	3
HS Code	29163990

Gefahreninformationscode (GHS)

(S)-(+)-Ibuprofen Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Dexibuprofen, the S-(+)-isomer of the widely used NSAID agent ibuprofen, was launched in Austria for the treatment of rheumatoid arthritis. While the racemic compound is commonly used clinically, the antiinflammatory activity is mediated via the S-isomer by inhibition of prostaglandin synthesis. It has also been demonstrated that the R-isomer is converted to the Santipode in vivo via a CoA thioester intermediate. Since CoA plays a pivotal role in intermediary metabolism and maintenance of the [acyl-CoA], generation of R-ibuprofen-CoA competitively inhibits many CoA-dependent reactions, which consequently produces perturbations of hepatocyte Intermediary metabolism and mitocondrial function. Pure S-ibuprofen usage, therefore, is preferred allowing a reduction in dosage level and an improved side effect profile.
Beschreibung
Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC₅₀s = 2.6 and 1.53, μM, respectively). It is commonly synthesized as a racemic mixture of (S)- and (R)-isomers. (S)-Ibuprofen is an enantiomer that more potently inhibits COX activity, thromboxane formation, and platelet aggregation than the (R)-form. (S)-Ibuprofen also inhibits activation of NF-κB more effectively than (R)-ibuprofen (IC₅₀s = 62 and 122 μM, respectively). However, the enantiomers are equipotent in blocking superoxide formation, β-glucuronidase release, and LTB₄ generation by stimulated neutrophils (IC₅₀ values range from 0.14 to 0.58 μM). A majority of (R)-ibuprofen can be inverted to (S)-ibuprofen in humans after oral administration.
Chemische Eigenschaften
Colourless, Crystalline Solid
Originator
Gebro Broschek (Austria)
Verwenden
Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53, μM, respectively). It is commonly synthesized as a racemic mixture of (S)- and (R)-isomers. (S)-Ibuprofen is an enantiomer that more potently inhibits COX activity, thromboxane formation, and platelet aggregation than the (R)-form. (S)-Ibuprofen also inhibits activation of NF-κB more effectively than (R)-ibuprofen (IC50s = 62 and 122 μM, respectively). However, the enantiomers are equipotent in blocking superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 0.14 to 0.58 μM). A majority of (R)-ibuprofen can be inverted to (S)-ibuprofen in humans after oral administration.
Verwenden
sedative
Verwenden
A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer
Definition
ChEBI: Dexibuprofen is an ibuprofen. It has a role as a non-narcotic analgesic and a non-steroidal anti-inflammatory drug. It is an enantiomer of a levibuprofen.
Trademarks
Seractil
Allgemeine Beschreibung
(S)-(+)-Ibuprofen is the enantiomer associated with the anti-inflammatory action of ibuprofen, which is widely used as a nonsteroidal anti-inflammatory drug in racemic form.
Biologische Aktivität
Non-steroidal anti-inflammatory drug (NSAID) that inhibits cyclooxygenase 1 and cyclooxygenase 2 (IC 50 values are 12 and 80 μ M respectively). Active isomer of ibuprofen.
Clinical Use
NSAID and analgesic
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect, increased risk of nephrotoxicity and hyperkalaemia.
Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage).
Antibacterials: possibly increased risk of convulsions with quinolones.
Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban.
Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin concentration.
Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir
Ciclosporin: may potentiate nephrotoxicity
Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib
Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics.
Lithium: excretion decreased.
Pentoxifylline: increased risk of bleeding.
Tacrolimus: increased risk of nephrotoxicity
Stoffwechsel
Dexibuprofen is the S(+)-enantiomer of ibuprofen. After metabolic transformation in the liver (hydroxylation and carboxylation), the pharmacologically inactive metabolites are completely excreted, mainly by the kidneys (90%), but also in the bile.
läuterung methode
Crystallise the (+) and (-) acids from EtOH or aqueous EtOH. The racemate which crystallises from pet ether with m 75-77o is sparingly soluble in H2O and has IR (film) 1705 (C=O), 2300—3700 (OH broad)cm-1. It is used as a non-steroidal anti-inflammatory. [Shiori et al. J Org Chem 43 2936 1978, Kaiser et al. J Pharm Sci 65 269 1976, J Pharm Sci 81 221 1992, Freer Acta Cryst (C) 49 1378 1993 for the (S+)-enantiomer.]

(S)-(+)-Ibuprofen Upstream-Materialien And Downstream Produkte

(S)-(+)-Ibuprofen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

51146-56-6, (S)-(+)-Ibuprofen Verwandte Suche:

Send Inquriy