Dexibuprofen (HCID 39912)

Überblick

Dexibuprofen is an ibuprofen. It has a role as a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is an enantiomer of a levibuprofen.

Namen und Bezeichner

Bevorzugter Name: Dexibuprofen
IUPAC: (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
Englischer Name: (S)-(+)-Ibuprofen
Summenformel: C13H18O2
Molmasse: 206.28

Namen und Synonyme

51146-56-6DEXIBUPROFENDexibuprofeneDexibuprofenoSeractild-Ibuproten(+)-(S)-p-Isobutylhydratropic acidDexibuprofenums-ibuprofen(2S)-2-(4-isobutylphenyl)propanoic acid(2S)-2-[4-(2-methylpropyl)phenyl]propanoic acidDTXSID9048724

Weitere Namen anzeigen

(S)-IBUPROFEN(S)-2-(4-Isobutylphenyl)propanoic acidRamelteon-7d-IbuprofenexibuprofenDeibuprofenDextroprofen

(+)-IbuprofenNSC-759814671DKG7P5S(S)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acidDTXCID6028650CHEBI:43415Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)-, (S)-(2S)-2-(4-(2-methylpropyl)phenyl)propanoic acid

Datenbank-Bezeichner

CAS: 51146-56-6
PubChem CID: 39912
DTXSID: DTXSID9048724
ChEMBL: CHEMBL175
ChEBI: CHEBI:43415
UNII: 671DKG7P5S
EC Number: 610-620-9
Nikkaji: J384.813B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,5
Polarare Oberfläche (TPSA): 37,3 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 4
Schwere Atome: 15
Formalladung: 0
Komplexität: 203

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

SolubilityInsoluble

Melting Point49-53

Physikochemische Eigenschaften

Schmelzpunkt: 49 · 49-53 °C(lit.)
Siedepunkt: 285.14 °C · 285.14°C (rough estimate)
Dichte: 1.0364 · 1.0364 (rough estimate)
Brechungsindex: 59 ° · 59 ° (C=2, EtOH)
Flammpunkt: 230 °F · >230 °F
storage temp.: Sealed in dry,Room Temperature
Löslichkeit: 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
Aggregatzustand: solid
pka: 4.41 · 4.41±0.10(Predicted)
Farbe: white
Wasserlöslichkeit: insoluble
BRN: 3590022 · 3590022
Stabilität: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/s1
InChIKey: HEFNNWSXXWATRW-JTQLQIEISA-N
SMILES: CC(C)Cc1ccc(cc1)[C@H](C)C(O)=O
CAS Datenbank: 51146 · 51146-56-6(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (85.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 7 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (85.7%)

Sicherheitsdaten

wgk: 3
hs_code: 29163990
risk_code: 63-22
hazard_code: Xn
safety_code: 45-36/37
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein BindingFor more information, refer to [ibuprofen].

PharmacodynamicsFor more information, refer to [ibuprofen].

Mechanism of Action · 1 Eintrag

Like common NSAIDs, dexibuprofen is an active enantiomer of [ibuprofen] that suppresses the prostanoid synthesis in the inflammatory cells via inhibition of the COX-2 isoform of the arachidonic acid COX. For more information, refer to [ibuprofen].

Biological Half-LifeOral tablets containing 300mg of dexibuprofen results in 2.2-4.7 hours. For more information, refer to [ibuprofen].

Metabolism/Metabolites · 2 Einträge

For more information, refer to [ibuprofen].

(S)-(+)-ibuprofen has known human metabolites that include 3-Hydroxyibuprofen and 2-Hydroxyibuprofen.

Verwendung und Herstellung

UsesUse (kg) in Switzerland (2009): >25000

Anwendungen · 2 Einträge

BeschreibungDexibuprofen, 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.

VerwendenA nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer