General
Preferred name
IBUPROFEN
Synonyms
(±)-Ibuprofen ()
R(-)-IBUPROFEN ()
DEXIBUPROFEN ()
(¡À)-Ibuprofe ()
NeoProfen ()
(??)-Ibuprofe ()
Motrin ()
Brufen ()
Advil ()
IBUPROFEN LYSINE ()
(¡À)-Ibuprofen ()
Ibuprofen (Advil) ()
(±)-Ibuprofen (sodium) ()
Ibuprofen (L-lysine) ()
Ibuprofen (sodium) ()
Ibuprofen (NSC 256857) ()
Dolgesic,NSC 256857 ()
(±)?-Ibuprofen-d3 ()
(±)-Ibuprofen-d3 (sodium salt) ()
Deep Relief ()
Midol Liquid Gels ()
Arthrofen 600 ()
Anadin LiquiFast ()
Lidifen ()
Seclodin ()
Ibutime ()
Ibu-Slo ()
Aches-N-Pain ()
Profen ()
Anadin Period Pain Relief ()
Children's Elixsure ()
Ibuleve ()
Ibu-Tab 200 ()
Nurofen For Child ()
Apsifen ()
U-18573 ()
Ebufac ()
Pacifene ()
Nurofen 400 ()
Phor Pain ()
Ibugel Fte ()
Children's Advil ()
Burana ()
Nurofen Sinus ()
Manorfen ()
Ibumousse ()
Junior Strength Ibuprofen ()
Rufen ()
Femafen ()
Fenbid Fte ()
Cuprofen For Child ()
Ibumed ()
Ibufac ()
Advil Migraine Liqui-Gels ()
Rimafen ()
Medipren ()
Codafen Continus ()
Novaprin ()
Nurofen Back Pain SR ()
Children'S Motrin ()
Migrafen ()
Fenbid ()
Lidifen-F ()
Cuprofen Plus ()
Ibugel ()
Children'S Ibuprofen ()
Anadin Joint Pain ()
IP-82 ()
Phensic ()
Motrin Ib ()
Ibuprofenum ()
Midol ()
Tab-Profen ()
NSC-256857 ()
Ibuspray ()
Nurofen Child ()
Brufen Ret ()
Pediatric Advil ()
Lobufen ()
Ibular ()
Maxa-Gesic ()
Children's Advil-Flavored ()
Ibuderm ()
Nurofen Solb ()
Nuprin ()
Ibucalm ()
Nurofen Recovery ()
Arthrofen 400 ()
Inabrin ()
Anadin Ultra ()
Junior Strength Motrin ()
Apsifen-F ()
Ibumetin ()
Proflex ()
Feverfen ()
Advil Liqui-Gels ()
U-18,573 ()
Fleximex ()
Phorpain Max Strgh ()
Phorpain ()
Mandafen ()
Paxofen ()
Inoven ()
Fenpaed ()
Nurofen Plus ()
Relcofen ()
Orbifen ()
Pedea ()
Motrin Migraine Pain ()
Cap-Profen ()
Co-Op ()
Ibuprohm ()
Infant's advil ()
Isisfen ()
Proflex Sr ()
Junior Strength Advil ()
Suspren ()
IB-100 ()
Caldolor ()
Ibuprin ()
M01AE01 ()
Junifen ()
Arthrofen 200 ()
RD 13621 ()
Ibu-Tab ()
Ibuprofen ()
Dolormin ()
Feminax Express ()
Ibuprofen lysinate ()
Saren ()
Nurofen Max Strgth Mig Pain ()
Imbun ()
Arfen ()
Solufenum ()
Lisiprofen ()
Nurofen Advance ()
Soluphene ()
Ibuprofen l-lysine ()
Nurofen Migraine Pain ()
Nurofen Tension Headache ()
IBUPROFEN SODIUM ()
Ibuprofen sodium dihydrate ()
Sodium ibuprofen dihydrate ()
Spedifen ()
Ibuprofen arginate ()
Dolo-spedifen ()
IBUPROFEN ARGININE ()
(±)-Ibuprofen (L-lysine) ()
P&D ID
PD002295
CAS
15687-27-1
57469-77-9
139466-08-3
121662-14-4
5264-06-2
31121-93-4
1010396-31-2
1185039-20-6
1219805-09-0
Tags
available
natural product
drug
drug candidate
Approved by
PMDA
FDA
First approval
2006
2012
1974
Drug indication
Pain
Anti-Inflammatory
Drug Status
investigational
approved
Max Phase
4.0
1.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCPRITION
A nonsteroidal anti-inflammatory agent with analgesic properties used in the treatment of RHEUMATISM and ARTHRITIS.
ROE
Ibuprofen is rapidly metabolized and eliminated in the urine thus, this via accounts for more than 90% of the administered dose. It is completely eliminated in 24 hours after the last dose and almost all the administered dose goes through metabolism, representing about 99% of the eliminated dose.[A39092] The biliary excretion of unchanged drug and active phase II metabolites represents 1% of the administered dose.[A39190]; ; In summary, ibuprofen is excreted as metabolites or their conjugates. The elimination of ibuprofen is not impaired by old age or the presence of renal impairment.[A39092]
TOXICITY
The symptoms of overdose are presented in individuals that consumed more than 99 mg/kg. Most common symptoms of overdose are abdominal pain, nausea, vomiting, lethargy, vertigo, drowsiness (somnolence), dizziness and insomnia. Other symptoms of overdose include headache, loss of consciousness, tinnitus, CNS depression, convulsions and seizures. May rarely cause metabolic acidosis, abnormal hepatic function, hyperkalemia, renal failure, dyspnea, respiratory depression, coma, acute renal failure, and apnea (primarily in very young pediatric patients).[A39200]; ; The reported LD50 of ibuprofen is of 636 mg/kg in rat, 740 mg/kg in mouse and 495 mg/kg in guinea pig.[MSDS]
DESCRIPTION
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID).
The approved drug is a racemic mixture of the (R)- and (S)-stereoisomers. The (S)-enantiomer is more active, and the (R)-enantiomer is converted in the body to the (S)-enantiomer. We show the non-isomeric molecule to represent the mixture. (GtoPdb)
The approved drug is a racemic mixture of the (R)- and (S)-stereoisomers. The (S)-enantiomer is more active, and the (R)-enantiomer is converted in the body to the (S)-enantiomer. We show the non-isomeric molecule to represent the mixture. (GtoPdb)
PHARMACODYNAMICS
Ibuprofen has multiple actions in different inflammatory pathways involved in acute and chronic inflammation. The main effects reported in ibuprofen are related to the control of pain, fever and acute inflammation by the inhibition of the synthesis of prostanoids by COX-1 and COX-2. Pain relief is attributed to peripheral affected regions and central nervous system effects in the pain transmission mediated by the dorsal horn and higher spinothalamic tract. Some reports have tried to link the pain regulation with a possible enhancement on the synthesis of endogenous cannabinoids and action on the NMDA receptors. The effect on pain has been shown to be related to the cortically evoked potentials.[A39190]; ; The antipyretic effect is reported to be linked to the effect on the prostanoid synthesis due to the fact that the prostanoids are the main signaling mediator of pyresis in the hypothalamic-preoptic region.[A39190]; ; The use of ibuprofen in dental procedures is attributed to the local inhibition of prostanoid production as well as to anti-oedemic activity and an increase of plasma beta-endorphins. Some reports have suggested a rapid local reduction of the expression of COX-2 in dental pulp derived by the administration of ibuprofen.[A39190]; ; The administration of ibuprofen in patients with rheumatic diseases has shown to control joint symptoms.[A39092] ; ; Ibuprofen is largely used in OTC products such as an agent for the management of dysmenorrhea which has been proven to reduce the amount of menstrual prostanoids and to produce a reduction in the uterine hypercontractility.[A39181] As well, it has been reported to reduce significantly the fever and the pain caused by migraines.[A39182, A39183] This effect is thought to be related to the effect on platelet activation and thromboxane A2 production which produces local vascular effects in the affected regions. This effect is viable as ibuprofen can enter in the central nervous system.[A39190]; ; In the investigational uses of ibuprofen, it has been reported to reduce neurodegeneration when given in low doses over a long time.[A39184] On the other hand, its use in Parkinson disease is related to the importance of inflammation and oxidative stress in the pathology of this condition.[A39185] The use of ibuprofen for breast cancer is related to a study that shows a decrease of 50% in the rate of breast cancer.[A39186]
MOA
The exact mechanism of action of ibuprofen is unknown. However, ibuprofen is considered an NSAID and thus it is a non-selective inhibitor of cyclooxygenase, which is an enzyme involved in prostaglandin (mediators of pain and fever) and thromboxane (stimulators of blood clotting) synthesis via the arachidonic acid pathway.[L4614]; ; Ibuprofen is a non-selective COX inhibitor and hence, it inhibits the activity of both COX-1 and COX-2. The inhibition of COX-2 activity decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling while the inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration.[A39195]
INDICATION
Ibuprofen is the most commonly used and prescribed NSAID. It is very common over the counter medication widely used as an analgesic, anti-inflammatory and antipyretic.[A39096]; ; The use of ibuprofen and its enantiomer [DB09213] in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder.[A39097]; ; Due to its activity against prostaglandin and thromboxane synthesis, ibuprofen has been attributed to alteration of platelet function and prolongation of gestation and labor.[A39092]; ; As ibuprofen is a widely used medication, the main therapeutic indications are:; ; * Patent Ductus Arteriosus - it is a neonatal condition wherein the ductus arteriosus (blood vessel that connects the main pulmonary artery to the proximal descending aorta) fails to close after birth causing severe risk of heart failure. The prostaglandin inhibition of ibuprofen has been studied for the treatment of this condition as it is known that prostaglandin E2 is responsible for keeping the ductus arteriosus open.[A39100]; ; * Rheumatoid- and osteo-arthritis - ibuprofen is very commonly used in the symptomatic treatment of inflammatory, musculoskeletal and rheumatic disorders.[A39176]; ; * Cystic fibrosis - the use of high dosages of ibuprofen has been proven to decrease inflammation and decreasing polymorphonuclear cell influx in the lungs.[A39177]; ; * Orthostatic hypotension - ibuprofen can induce sodium retention and antagonize the effect of diuretics which has been reported to be beneficial for patients with severe orthostatic hypotension.[A1651]; ; * Dental pain - ibuprofen is used to manage acute and chronic orofacial pain.[A10901]; ; * Minor pain - ibuprofen is widely used to reduce minor aches and pains as well as to reduce fever and manage dysmenorrhea. It is very commonly used for the relief of acute indications such as fever and tension headaches.[A39092]; ; * Investigational uses - efforts have been put into developing ibuprofen for the prophylaxis of Alzheimer's disease, Parkinson disease, and breast cancer.[A39092]
METABOLISM
Ibuprofen is rapidly metabolized and biotransformed in the liver to the formation of major metabolites which are the hydroxylated and carboxylated derivatives.[A39092] As soon as it is absorbed, the R-enantiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer _in vivo_ by the activity of alpha-methylacyl-CoA racemase.[A39194] ; ; Ibuprofen metabolism can be divided in phase I which is represented by the hydroxylation of the isobutyl chains for the formation of 2 or 3-hydroxy derivatives followed by oxidation to 2-carboxy-ibuprofen and p-carboxy-2-propionate. These oxidative reactions are performed by the activity of the cytochrome P450 isoforms CYP 2C9, CYP 2C19 and CYP 2C8. Therefore, these enzymes participate in the oxidation of the alkyl side chain to hydroxyl and carboxyl derivatives. From this enzymes, the major catalyst in the formation of oxidative metabolites is the isoform CYP 2C9.[A39190]; ; The metabolic phase I is followed by a phase II in which the oxidative metabolites may be conjugated to glucuronide prior to excretion. This activity forms phenolic and acyl glucuronides.[A39190]
ABSORPTION
It is very well absorbed orally and the peak serum concentration can be attained in 1 to 2 hours after extravascular administration. When ibuprofen is administered immediately after a meal there is a slight reduction in the absorption rate but there is no change in the extent of the absorption.[A39092] ; ; When orally administered, the absorption of ibuprofen in adults is very rapidly done in the upper GI tract.[A39190] The average Cmax, Tmax and AUC ranges around 20 mcg/ml, 2 h and 70 mcg.h/ml. These parameters can vary depending on the enantiomer form, route, and dose of administration.[A39190]
DESCRIPTION
Anti-inflammatory and analgesic; non-selective COX inhibitor
(LOPAC library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
4
Organisms
2
Compound Sets
30
AdooQ Bioactive Compound Library
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
Ki Database
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
136
Molecular Weight
206.13
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
1
Rotatable Bonds
4
Ring Count
1
Aromatic Ring Count
1
cLogP
3.07
TPSA
37.3
Fraction CSP3
0.46
Chiral centers
1.0
Largest ring
6.0
QED
0.82
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
COX
Pathway
Neuroscience
Immunology/Inflammation
Anti-infection
Apoptosis
Target
COX-1
COX-2
Parasite
Member status
virtual
MOA
Cyclooxygenase-3 Inhibitors
Cyclooxygenase-1 Inhibitors
Cyclooxygenase-2 Inhibitors
Non-Steroidal Antiinflammatory Drugs
NF-kappaB (NFKB) Activation Inhibitors
Therapeutic Class
Analgesics
Source data
