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Details

Stereochemistry MIXED
Molecular Formula C13H18O2.C6H14N2O2
Molecular Weight 352.4684
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBUPROFEN DL-LYSINE

SMILES

NCCCCC(N)C(O)=O.CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

InChI

InChIKey=IHHXIUAEPKVVII-UHFFFAOYSA-N
InChI=1S/C13H18O2.C6H14N2O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;7-4-2-1-3-5(8)6(9)10/h4-7,9-10H,8H2,1-3H3,(H,14,15);5H,1-4,7-8H2,(H,9,10)

HIDE SMILES / InChI

Description

Ibuprofen is a nonsteroidal anti-inflammatory agent (NSAIA) or nonsteroidal anti-inflammatory drug (NSAID), with analgesic and antipyretic properties. Ibuprofen has pharmacologic actions similar to those of other prototypical NSAIAs, which are thought to act through inhibition of prostaglandin synthesis. It’s used temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps and temporarily reduces fever. The exact mechanism of action of ibuprofen is unknown. Ibuprofen is a non-selective inhibitor of cyclooxygenase, an enzyme invovled in prostaglandin synthesis via the arachidonic acid pathway. Its pharmacological effects are believed to be due to inhibition cylooxygenase-2 (COX-2) which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration. Ibuprofen is administered as a racemic mixture. The R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo. The S-enantiomer is believed to be the more pharmacologically active enantiomer.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
IBU-TAB
Palliative
IBU-TAB
Palliative
IBU-TAB
Palliative
IBU-TAB
Palliative
IBU-TAB

Cmax

ValueDoseCo-administeredAnalytePopulation
27.9 μg/mL
400 mg single, oral
IBUPROFEN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
103 μg × h/mL
400 mg single, oral
IBUPROFEN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.2 h
400 mg single, oral
IBUPROFEN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
IBUPROFEN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
adults: take 1 tablet every 4 to 6 hours while symptoms persist. If pain or fever does not respond to 1 tablet, 2 tablets may be used; do not exceed 6 tablets in 24 hours. Children under 12 years: ask a doctor.
Route of Administration: Oral
In Vitro Use Guide
Ibuprofen, in a 400-μM concentration, decreased the expression of Hsp70 by 23% in comparison with untreated cells, whereas other NSAID had no effect. Ibuprofen also decreased the expression of Hsp70 in H358, a human lung adenocarcinoma cell line, in a dose-dependent manner (from 0-400 uM).