(S)-(+)-Ibuprofen - ≥98%(GC) , Cyclooxygenase inhibitor, CAS No.51146-56-6, Cyclooxygenase inhibitor

CAS: 51146-56-6 Cat. No.: S140886 Peso molecular: 206.28 Beilstein Registry Number: 3590022 Número EC: 610-620-9

GRADE & PURITY ≥98%(GC)

Synonyms

Dexibuprofenum | Dexibuprofenum [INN-Latin] | (+)-(S)-Ibuprofen | AB00513957 | Prestwick1_000907 | S-(+)-ibuprofen | S(+)-Ibuprofen | UNII-671DKG7P5S | (S)-2-(4-Isobutylphenyl)propanoic acid | (S)-2-(4-Isobutylphenyl)propionic acid | (S)-2-(4-isobutyl-phe

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

(S)-Ibuprofen is the active enantiomer of ibuprofen. (S)-Ibuprofen inhibits Cox-1 and Cox-2 with comparable potency (ID50 = 8.9-14 μM and 7.2-8.2 μM, respectively). (S)-Ibuprofen acts as a non-steroidal analgesic and antiinflammatory agent. This compound’s inhibition of Cox-1 and Cox-2 and activation of PPARα and PPARγ isoforms may be responsible for its pharmacological effects. (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.
Enantiomeric form of the anti-inflammatory agent ibuprofen used in pharmacokinetic studies.

Specifications

Sinónimos

Dexibuprofenum | Dexibuprofenum [INN-Latin] | (+)-(S)-Ibuprofen | AB00513957 | Prestwick1_000907 | S-(+)-ibuprofen | S(+)-Ibuprofen | UNII-671DKG7P5S | (S)-2-(4-Isobutylphenyl)propanoic acid | (S)-2-(4-Isobutylphenyl)propionic acid | (S)-2-(4-isobutyl-phe

Especificaciones y pureza

≥98%(GC)

Mecanismos bioquímicos y fisiológicos

Non-selective COX inhibitor (IC 50 values are 2.9 and 1.1 μM for COX1 and COX2, respectively). Non-steroidal anti-inflammatory drug (NSAID). Rapidly crosses the blood-brain barrier.

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Mecanismo de acción

Cyclooxygenase inhibitor

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%(GC)

Propiedades del producto

• ALogP: 3.5

Nombres e identificadores

• Pubchem Sid: 504753594
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753594
• Sonrisas canónicas: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
• IUPAC Name: (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
• InChIKey: HEFNNWSXXWATRW-JTQLQIEISA-N
• 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
• Isómeros SMILES: C[C@@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
• WGK Alemania: 3
• Peso molecular: 206.28
• Beilstein: 3590022
• Reaxy-Rn: 2049713
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2049713&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Phenylpropanoic acids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Phenylpropanoic acids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpropanoic acids
• Alternative Parents: Monocyclic monoterpenoids Aromatic monoterpenoids Phenylpropanes Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 2-phenylpropanoic-acid - P-cymene - Aromatic monoterpenoid - Monocyclic monoterpenoid - Monoterpenoid - Phenylpropane - Monocyclic benzene moiety - Benzenoid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Carbonyl group - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
• External Descriptors: ibuprofen

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

PTGS1 Tclin Prostaglandin G/H synthase 1 (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PTGS2 Tclin Prostaglandin G/H synthase 2 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CALCR Tclin Calcitonin receptor (2215 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ltc4s Leukotriene C4 synthase (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Sigmar1 Sigma opioid receptor (160 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Saccharomyces cerevisiae (19171 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pfk 6-phospho-1-fructokinase (7870 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Brain (1 Activities)

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Plasma (328 Activities)

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nfo Endonuclease 4 (425 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NS1 Nonstructural protein 1 (33327 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ptgs1 Prostaglandin G/H synthase (cyclooxygenase) (169 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Asic1 Acid-sensing ion channel 1 (41 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Asic2 Acid-sensing ion channel 2 (38 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Glra2 Glycine receptor (1745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in DMSO (100 mM), ethanol (100 mM), dichloromethane, ethyl acetate, and methanol. Insoluble in water.
• Rotación específica [α]: 59°
• Punto de inflamación (°F): >235.4 °F
• Punto de inflamación (°C): >113 °C
• Punto de fusión (°C): 49-53°C
• Peso molecular: 206.280 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 206.131 Da
• Monoisotopic Mass: 206.131 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 203.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Dan Xiao, Ying Jin, Mengyu Zhang, Xiangjie Di, Lisha Fu, Changke Jiang, Zhuoli Lai, Yating Ge, Shanmian Ji, Yuming Zhang, Li Zheng, Zhenlei Wang, Fang Gong.  (2023)  Chiral pharmacokinetics of ibuprofen enantiomers in Chinese preterm neonates with patent ductus arteriosus using a validated UHPLC-MS/MS method.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:37454407] [10.1016/j.jchromb.2023.123765]

2. Zhenfei Wang, Bin Liang, Yanan Hou, Si Li, Li Xie, Liang Peng, Peng Zhang, Aijie Wang, Hui Yun, Xiangkai Li.  (2022)  Weak electrostimulation enhanced the microbial transformation of ibuprofen and naproxen.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:35489501] [10.1016/j.scitotenv.2022.155522]

3. Zefang Wang, Yan Peng, Chengjun Shi, Liping Wang, Xiaohong Chen, Wanwan Wu, Xu Wu, Yiming Zhu, Jingchen Zhang, Guiliang Cheng, Songlin Zhuang.  (2021)  Qualitative and quantitative recognition of chiral drugs based on terahertz spectroscopy.  ANALYST,  146  (12): (3888-3898).  [PMID:34042921] [10.1039/D1AN00500F]

4. Qian Han, Cun Wang, Pingkun Liu, Gui Zhang, Li Song, Yingzi Fu.  (2021)  Achieving synergistically enhanced dual-mode electrochemiluminescent and electrochemical drug sensors via a multi-effect porphyrin-based metal-organic framework.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2020.129388]

5. Fang Wang, Bin Wang, Han Qu, Wenxing Zhao, Lei Duan, Yizhe Zhang, Yitong Zhou, Gang Yu.  (2020)  The influence of nanoplastics on the toxic effects, bioaccumulation, biodegradation and enantioselectivity of ibuprofen in freshwater algae Chlorella pyrenoidosa.  ENVIRONMENTAL POLLUTION,      [PMID:32315820] [10.1016/j.envpol.2020.114593]

6. Mingxia Liu, Lixia Chen, Tingting Tian, Zhiguo Zhang, Xiangjun Li.  (2019)  Identification and Quantitation of Enantiomers by Capillary Electrophoresis and Circular Dichroism Independent of Single Enantiomer Standard.  ANALYTICAL CHEMISTRY,      [PMID:31591882] [10.1021/acs.analchem.9b03276]

7. Tuanjia Li, Wangchuan Xiao, Shizhao Ren, Rongrong Xue, Fenghua Chen.  (2024)  Metastable Racemic Ibuprofen Supercooled Liquid.  Crystals,  14  (12): (1037).  [PMID:] [10.3390/cryst14121037]

8. Duo Xu, Yantian Ji, Bowen Du, Bo He, Hongyang Chen, Huimin Sun, Xianqiang Yin.  (2024)  The synergistic effect of typical chiral organic acids and solution chemistry conditions on the transport of 2-arylpropionic acid chiral derivatives in porous media.  ENVIRONMENTAL POLLUTION,      [PMID:38703979] [10.1016/j.envpol.2024.124059]

9. Lumei Dai, Shifang Wen, Yaling Chen, Xinchun Li, Bing Zhao, Xinyu You, Rongqiang Li, Bin Zhang.  (2025)  Self-assembled dual-target ibuprofen-irinotecan conjugate for colorectal cancer therapy.  BIOORGANIC & MEDICINAL CHEMISTRY,      [PMID:40850193] [10.1016/j.bmc.2025.118367]