ChemicalBook > CAS DataBase List > (S)-(+)-Ibuprofen

(S)-(+)-Ibuprofen

Product Name
(S)-(+)-Ibuprofen
CAS No.
51146-56-6
Chemical Name
(S)-(+)-Ibuprofen
Synonyms
DEXIBUPROFEN;(S)-IBUPROFEN;(S)-2-(4-Isobutylphenyl)propanoic acid;Seractil;Ramelteon-7;d-Ibuprofen;exibuprofen;Deibuprofen;Dextroprofen;(+)-Ibuprofen
CBNumber
CB0699655
Molecular Formula
C13H18O2
Formula Weight
206.28
MOL File
51146-56-6.mol
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(S)-(+)-Ibuprofen Property

Melting point:
49-53 °C(lit.)
alpha 
57 º (c=2, EtOH)
Boiling point:
285.14°C (rough estimate)
Density 
1.0364 (rough estimate)
refractive index 
59 ° (C=2, EtOH)
Flash point:
>230 °F
storage temp. 
Sealed in dry,Room Temperature
solubility 
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
form 
solid
pka
4.41±0.10(Predicted)
color 
white
optical activity
[α]20/D +59°, c = 2 in ethanol
Water Solubility 
insoluble
BRN 
3590022
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
HEFNNWSXXWATRW-JTQLQIEISA-N
CAS DataBase Reference
51146-56-6(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
63-22
Safety Statements 
45-36/37
WGK Germany 
3
HS Code 
29163990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
375160
Product name
(S)-(+)-Ibuprofen
Purity
ReagentPlus , 99%
Packaging
1g
Price
$58.3
Updated
2024/03/01
Sigma-Aldrich
Product number
375160
Product name
(S)-(+)-Ibuprofen
Purity
ReagentPlus , 99%
Packaging
5g
Price
$117
Updated
2024/03/01
TCI Chemical
Product number
I0549
Product name
(S)-(+)-2-(4-Isobutylphenyl)propionic Acid
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$27
Updated
2024/03/01
TCI Chemical
Product number
I0549
Product name
(S)-(+)-2-(4-Isobutylphenyl)propionic Acid
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$77
Updated
2024/03/01
Cayman Chemical
Product number
16793
Product name
(S)-Ibuprofen
Purity
≥98%
Packaging
1g
Price
$43
Updated
2024/03/01
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(S)-(+)-Ibuprofen Chemical Properties,Usage,Production

Description

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.

Description

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.

Chemical Properties

Colourless, Crystalline Solid

Originator

Gebro Broschek (Austria)

Uses

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

Uses

sedative

Uses

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.

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.

brand name

Seractil

General Description

(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.

Biological Activity

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

Drug interactions

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

Metabolism

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.

Purification Methods

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-(+)-Ibuprofen Suppliers

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View Lastest Price from (S)-(+)-Ibuprofen manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
(S)-(+)-Ibuprofen 51146-56-6
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%-101%
Supply Ability
1000kgs
Release date
2021-08-03
Hebei Weibang Biotechnology Co., Ltd
Product
(S)-(+)-Ibuprofen 51146-56-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-31
Hebei Chuanghai Biotechnology Co,.LTD
Product
(S) - (+) -Ibuprofen 51146-56-6
Price
US $5.70/KG
Min. Order
10KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21

51146-56-6, (S)-(+)-Ibuprofen Related Search:

Imidocarb dipropionate Isobutyl nitrite IBUPROFEN,α-Methyl-4-(isobutyl)phenylacetic acid, Ibuprofen,Ibuprofen (FDA),rac Ibuprofen,R,S-Ibuprofen,(+/-)-IBUPROFEN 1-Bromo-2-methylpropane α-Lipoic Acid Propionic acid Nandrolone phenylpropionate 3-(4-Hydroxyphenyl)propionic acid Ethyl 2-(Chlorosulfonyl)acetate PHENYL VALERATE 3-Phenylpropionic acid Isobutylbenzene Propionic anhydride Phenylacetic acid isobutyl ester Ascoric Acid IBUPROFEN IMPURITY E,IBUPROFEN IMP E IBUPROFEN IMP D,IBUPROFEN IMPURITY D IBUPROFEN IMPURITY J

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  • (S)-(+)-IbuprofenQ: What is (S)-(+)-Ibuprofen Q: What is the CAS Number of (S)-(+)-Ibuprofen Q: What is the storage condition of (S)-(+)-Ibuprofen
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  • 51146-56-6
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  • Cyclooxygenase Inhibitors
  • Enzymes, Inhibitors, and Substrates
  • Organic Building Blocks
  • Biochemicals and Reagents
  • Application Index