Dexibuprofen (HCID 39912)

概要

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.

名称と識別子

優先名称: Dexibuprofen
IUPAC: (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
現地名: デキシブプロフェン
英語名: (S)-(+)-Ibuprofen
分子式: C13H18O2
分子量: 206.28

名称と別名

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

名称をさらに表示

(S)-(+)-2-(4-イソブチルフェニル)プロピオン酸(S)-イブプロフェンS-(+)-イブプロフェンS(+)-イブプロフェン(S)-2-(p-イソブチルフェニル)プロピオン酸[αS,(+)]-α-メチル-4-(2-メチルプロピル)ベンゼン酢酸[S,(+)]-2-(4-イソブチルフェニル)プロピオン酸(S)-2-(4-イソブチルフェニル)プロピオン酸(+)-(S)-イブプロフェンデキスイブプロフェンデキシブプロフェン(2S)-2-(4-イソブチルフェニル)プロピオン酸[S,(+)]-α-メチル-4-(2-メチルプロピル)ベンゼン酢酸[2S,(+)]-2-[4-(2-メチルプロピル)フェニル]プロパン酸(S)-α-メチル-4-イソブチルベンゼン酢酸(+)-イブプロフェン(S)-2-(4-イソブチルフェニル)プロパン酸(αS)-α-メチル-4-イソブチルベンゼン酢酸(S)-α-メチル-4-(2-メチルプロピル)ベンゼン酢酸(2S)-2-(4-イソブチルフェニル)プロパン酸(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

データベース識別子

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

物性

構造計算による物性

XLogP: 3.5
極性表面積: 37.3 Å²
水素結合供与体数: 1
水素結合受容体数: 2
回転可能結合数: 4
重原子数: 15
形式電荷: 0
複雑度: 203

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

SolubilityInsoluble

Melting Point49-53

物理化学的性質

融点: 49 · 49-53 °C(lit.)
比旋光度: 57 · 57 º (c=2, EtOH)
沸点: 285.14 °C · 285.14°C (rough estimate)
比重(密度): 1.0364 · 1.0364 (rough estimate)
屈折率: 59 ° · 59 ° (C=2, EtOH)
闪点: 230 °F · >230 °F
貯蔵温度: Sealed in dry,Room Temperature
溶解性: 45 % · 45% (w/v) 2-ヒドロキシプロピル-β-シクロデキストリン水溶液: 1.5mg/mL
外見: 個体
酸解離定数(Pka): 4.41 · 4.41±0.10(Predicted)
色: 白い
水溶解度: 不溶性
BRN: 3590022 · 3590022
安定性: 安定。強力な酸化剤とは相容れない。
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 データベース: 51146 · 51146-56-6(CAS DataBase Reference)

化学的性質

化学的特性Colourless, Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (85.7%)

安全データ

wgk: 3
hs_code: 29163990
risk_code: 63-22
hazard_code: Xn
safety_code: 45-36/37
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 2 件

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 件

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 件

For more information, refer to [ibuprofen].

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

用途と製造

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

応用分野 · 3 件

説明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.

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

一般的な説明(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.

調製方法 · 1 件

純化方法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.]