Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H18O2 |
Molecular Weight | 206.2808 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(O)=O
InChI
InChIKey=HEFNNWSXXWATRW-UHFFFAOYSA-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)
Molecular Formula | C13H18O2 |
Molecular Weight | 206.2808 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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
PubMed
Title | Date | PubMed |
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Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries. | 2001 |
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Non-steroidal anti-inflammatory drugs protect against chondrocyte apoptotic death. | 2001 |
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Interpolymer complexation. II. Entrapment of ibuprofen by in-situ complexation between polyvinyl acetate phthalate (PVAP) and polyvinylpyrrolidone (PVP) and development of a chewable tablet formulation. | 2001 |
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A benefit/risk analysis of the prevention of brain ischaemia with anticoagulant drugs: when, how and whom to treat? | 2001 |
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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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[Misuse of drugs in recreational sports]. | 2001 Apr |
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Reversible binding of the novel anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid to plasma proteins and its distribution into blood cells in various species. | 2001 Apr |
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Obsessive-compulsive disorder: a neuronal membrane phospholipid hypothesis and concomitant therapeutic strategy. | 2001 Apr |
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Group B Streptococci and inducible nitric oxide synthase: modulation by nuclear factor kappa B and ibuprofen. | 2001 Apr |
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Ibuprofen-lysine for closure of patent ductus arteriosus. | 2001 Apr |
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In vitro effect of different non-steroidal anti-inflammatory drugs on human polymorphonuclear leukocyte activity measured by luminol-dependent chemiluminescence of the whole blood. | 2001 Apr |
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Ibuprofen-induced bullous leukocytoclastic vasculitis. | 2001 Apr |
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Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. | 2001 Apr |
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Induced accumulation of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) in maize leaves. | 2001 Apr |
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Renal failure and vestibular toxicity in an adolescent with cystic fibrosis receiving gentamicin and standard-dose ibuprofen. | 2001 Apr |
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Nonsurgical female sterilization: comparison of intrauterine application of quinacrine alone or in combination with ibuprofen. | 2001 Apr |
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Percutaneous, intramuscular neuromuscular electrical stimulation for the treatment of shoulder subluxation and pain in chronic hemiplegia: a case report. | 2001 Apr |
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Nitric oxide-releasing nonsteroidal anti-inflammatory drugs (NSAIDs) alter the kinetics of human colon cancer cell lines more effectively than traditional NSAIDs: implications for colon cancer chemoprevention. | 2001 Apr 15 |
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IL-10 mediation of activation-induced TH1 cell apoptosis and lymphoid dysfunction in polymicrobial sepsis. | 2001 Apr 7 |
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Investigational COX-2 inhibitor relieves pain in dental model. | 2001 Feb |
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Determination of nonsteroidal anti-inflammatory drugs in biological fluids by automatic on-line integration of solid-phase extraction and capillary electrophoresis. | 2001 Feb |
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The use of anti-inflammatory drugs in cancer pain. | 2001 Feb |
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[Topical administration is better than oral administration]. | 2001 Feb 1 |
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The involvement of phospholipase A(2) in ethanol-induced gastric muscle contraction. | 2001 Feb 16 |
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Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry. | 2001 Feb 23 |
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Activity profile of glycolamide ester prodrugs of ibuprofen. | 2001 Jan |
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Is the combination of ibuprofen and caffeine effective for the treatment of a tension-type headache? | 2001 Jan |
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Analgesia for colposcopy: double-masked, randomized comparison of ibuprofen and benzocaine gel. | 2001 Jan |
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Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg. | 2001 Jan 10 |
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Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs. | 2001 Jan 19 |
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Penetration enhancement of ibuprofen from supersaturated solutions through human skin. | 2001 Jan 5 |
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Pharmacokinetics of celecoxib in the presence and absence of interferon-induced acute inflammation in the rat: application of a novel HPLC assay. | 2001 Jan-Apr |
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Investigation of foreign substances in food. | 2001 Jan-Feb |
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Allergic reactions due to ibuprofen in children. | 2001 Jan-Feb |
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[Necrotizing fasciitis. Clinical criteria and risk factors]. | 2001 Mar |
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Synthesis of N-pyridinyl(methyl)-1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamides and analogues and their anti-inflammatory activity in mice and rats. | 2001 Mar |
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Synthesis and hydrolytic behaviour of glycerol-1,2-diibuprofenate-3-nitrate, a putative pro-drug of ibuprofen and glycerol-1-nitrate. | 2001 Mar |
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Inhibitors of arachidonic acid metabolism have variable effects on calcium signaling pathways. | 2001 Mar |
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Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals. | 2001 Mar |
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Association of human herpesvirus 6 infection with drug reaction with eosinophilia and systemic symptoms. | 2001 Mar |
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Analysis of nonsteroidal antiinflammatory drugs in meconium and its relation to persistent pulmonary hypertension of the newborn. | 2001 Mar |
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Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water. | 2001 Mar 16 |
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Use of glucosamine and chondroitin sulfate in the management of osteoarthritis. | 2001 Mar-Apr |
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Invasive group A streptococcal infection and nonsteroidal antiinflammatory drug use among children with primary varicella. | 2001 May |
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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Indomethacin and telomerase activity in tumor growth retardation. | 2001 May |
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Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations. | 2001 May 1 |
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Chemical reactivity in solid-state pharmaceuticals: formulation implications. | 2001 May 16 |
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Microencapsulation of ibuprofen and Eudragit RS 100 by the emulsion solvent diffusion technique. | 2001 May 7 |
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Inverse association of non-steroidal anti-inflammatory drugs and malignant melanoma among women. | 2001 May-Jun |
Patents
Sample Use Guides
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
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Oct 21 20:46:09 UTC 2019
by
admin
on
Mon Oct 21 20:46:09 UTC 2019
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Record UNII |
WK2XYI10QM
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N02AJ19
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LIVERTOX |
495
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NDF-RT |
N0000000160
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WHO-VATC |
QM02AA13
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WHO-ATC |
G02CC01
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WHO-ESSENTIAL MEDICINES LIST |
7.1
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FDA ORPHAN DRUG |
100896
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WHO-ESSENTIAL MEDICINES LIST |
8.4
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WHO-ATC |
M01AE51
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NDF-RT |
N0000175721
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EU-Orphan Drug |
EU/3/01/020
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WHO-VATC |
QM01AE51
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WHO-VATC |
QM01AE01
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WHO-VATC |
QG02CC01
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NDF-RT |
N0000175722
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NCI_THESAURUS |
C1323
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WHO-ATC |
R02AX02
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WHO-ATC |
M01AE01
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WHO-ATC |
N02AJ08
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WHO-ATC |
C01EB16
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EMA ASSESSMENT REPORTS |
PEDEA (AUTHORIZED: DUCTUS ATERIOSUS, PATENT)
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WHO-ESSENTIAL MEDICINES LIST |
29
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WHO-ESSENTIAL MEDICINES LIST |
2.1
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WHO-ATC |
M02AA13
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WHO-VATC |
QC01EB16
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M6189
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PRIMARY | Merck Index | ||
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CHEMBL521
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C561
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15687-27-1
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D007052
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58560-75-1
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DB01050
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2118
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5640
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2713
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239-784-6
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139466-08-3
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15687-27-1
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15687-27-1
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IBUPROFEN
Created by
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odour, characteristic. Solubility: Practically insoluble in water; soluble in 1.5 parts of ethanol (~750 g/l) TS, in 2 parts of ether R and in 1.5 parts of acetone R. Category: Analgesic; anti-inflammatory. Storage: Ibuprofen should be kept in a well-closed container. Definition: Ibuprofen contains not less than 98.5% and not more than 100.5% of C13H18O2, calculated with reference to the dried substance. | ||
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3672
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15687-27-1
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IBUPROFEN
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SUB08098MIG
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MINOR
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
MAJOR
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
MAJOR
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METABOLITE INACTIVE -> PARENT |
MINOR
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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MAXIMUM TOLERATED DOSE | PHARMACOKINETIC |
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INDICATION BIOLOGICAL PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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PEDIATRICS PHARMACOKINETIC |
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Cmax | PHARMACOKINETIC |
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ROUTE OF ADMINSTRATION PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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FOOD EFFECT PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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