Ibuprofen

Modify Date: 2024-01-02 15:18:17

Ibuprofen Structure
Ibuprofen structure
 Common Name Ibuprofen
CAS Number 15687-27-1 Molecular Weight 206.281
Density 1.0±0.1 g/cm3 Boiling Point 319.6±11.0 °C at 760 mmHg
Molecular Formula C13H18O2 Melting Point 77-78 °C(lit.)
MSDS Chinese USA Flash Point 216.7±14.4 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Ibuprofen


Ibuprofen is an anti-inflammatory inhibitor targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively.

 Names

Name ibuprofen
Synonym More Synonyms

 Ibuprofen Biological Activity

Description Ibuprofen is an anti-inflammatory inhibitor targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively.
Related Catalog
Target

COX-1:13 μM (IC50)

COX-2:370 μM (IC50)

In Vitro Ibuprofen inhibits the enzyme cyclooxygenase COX-1 and COX-2, which convert arachidonic acid to prostaglandin H2 (PGH2). Its action is similar to aspirin, indomethacin and all other NSAIDs in intact cells, broken cells, and purified enzyme preparations[1]. Ibuprofen inhibits the constitutive activation of NF-κB and IKKα in the androgen-independent prostate tumor cells PC-3 and DU-145. It sensitizes prostate cells to ionizing radiation and blocks stimulated activation of NF-κB following exposure to TNFα or ionizing radiation in the androgen-sensitive prostate tumor cell line LNCaP. Both of these cannot be attributed directly to inhibition of IκB-α kinase but to inhibition of an upstream regulator of IKKα[2]. Ibuprofen exerts an anticancer effect by reducing survival of cancer cells. Ibuprofen is more efficacious than aspirin and acetaminophen, and comparable with (R)-flurbiprofen and indomethacin in induction of p75NTR protein expression in cell lines from bladder and other organs[3].
In Vivo Ibuprofen reacts with the heme group of cyclooxygenase to prevent arachidonic acid conversion. Prior exposure to Ibuprofen in vivo protects cyclooxygenase completely from the irreversible effects of aspirin in platelets[4]. Ibuprofen treatment is effective in attenuating joint inflammation and early articular cartilage degeneration in the adult female Sprague-Dawley rat model induced by high-repetition and high-force (HRHF) task. It dose this by blocking the increases in serum C1 and 2C (a biomarker of collagen I and II degradation) as well as the ratio of collagen degradation to synthesis (C1, 2C/CPII, the latter a biomarker of collage type II synthesis) induced by HRHF[5].
Cell Assay The number of cells in each well after treatment (48 hours) with NSAIDs is estimated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. MTT labeling reagent (final concentration, 0.5 mg/mL) is added to each of the NSAID-treated T24 cells, ponasterone A alone-treated cells, ΔDDp75NTR-transfected cells plus ponasterone A, and ΔICDp75NTR-transfected cells plus ponasterone A (2×103 cells/well) in 96-well culture plates (final volume, 100 μL culture medium/well) and incubated for 4 hours at 37°C in a humidified atmosphere of 10% CO2. Subsequently, cells are incubated overnight with 100 μL of solubilization solution per well, and the samples are quantified at 570 nm using a microtiter plate reader.
Animal Admin At the end of the 4th week of task performance, subcohorts of the above animals are administered ibuprofen in drinking water daily (45 mg/kg body weight): NC+IBU (n=10), TR + IBU (n=11) and HRHF + IBU (n=15). HRHF+IBU animals continue to perform the HRHF task regimen with ibuprofen treatment for the remainder of the 12-week task period (i.e., an 8-week course of ibuprofen treatment). The dose used is lower than the maximum limit for gastrointestinal toxicity in rats, yet has been shown to be effective in reducing chronic inflammation. The amount of medicated water consumed/day is tracked for each animal by measuring the difference between the initial and final volume of suspended solution daily. Based on these assessments, the average weekly ibuprofen dose is similar in all groups (48.8±6.3 mg/kg body weight), with no significant differences in ibuprofen dose administered or serum levels of ibuprofen between the treated groups.
References

[1]. Noreen Y, et al. Development of a radiochemical cyclooxygenase-1 and -2 in vitro assay for identification of natural products as inhibitors of prostaglandin biosynthesis. J Nat Prod. 1998 Jan;61(1):2-7.

[2]. Palayoor ST, et al. Constitutive activation of IkappaB kinase alpha and NF-kappaB in prostate cancer cells is inhibited by ibuprofen. Oncogene. 1999 Dec 2;18(51):7389-94.

[3]. Khwaja F, et al. Ibuprofen inhibits survival of bladder cancer cells by induced expression of the p75NTR tumor suppressor protein. Cancer Res. 2004 Sep 1;64(17):6207-13.

[4]. Rao GH, et al. Ibuprofen protects platelet cyclooxygenase from irreversible inhibition by aspirin. Arteriosclerosis. 1983 Jul-Aug;3(4):383-8.

[5]. Driban JB, et al. Joint inflammation and early degeneration induced by high-force reaching are attenuated by ibuprofen in an animal model of work-related musculoskeletal disorder. J Biomed Biotechnol. 2011;2011:691412

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 319.6±11.0 °C at 760 mmHg
Melting Point 77-78 °C(lit.)
Molecular Formula C13H18O2
Molecular Weight 206.281
Flash Point 216.7±14.4 °C
Exact Mass 206.130676
PSA 37.30000
LogP 3.72
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.519
Storage condition -20?C Freezer
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility insoluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MU6640000
CHEMICAL NAME :
Hydratropic acid, p-isobutyl-
CAS REGISTRY NUMBER :
15687-27-1
LAST UPDATED :
199801
DATA ITEMS CITED :
47
MOLECULAR FORMULA :
C13-H18-O2
MOLECULAR WEIGHT :
206.31
WISWESSER LINE NOTATION :
QVY&R DIY

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
180 mg/kg/3W-I
TOXIC EFFECTS :
Liver - jaundice, cholestatic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Behavioral - coma Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - metabolic acidosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1028 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - changes in potassium Nutritional and Gross Metabolic - metabolic acidosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
8 mg/kg
TOXIC EFFECTS :
Behavioral - headache Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
120 mg/kg/W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
480 mg/kg/17D-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), diffuse Immunological Including Allergic - uncharacterized Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
171 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
469 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
429 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - respiratory obstruction Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - metabolic acidosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
132 mg/kg/6D-I
TOXIC EFFECTS :
Blood - thrombocytopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
96 mg/kg/3D-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - diplopia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
636 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
626 mg/kg
TOXIC EFFECTS :
Behavioral - analgesia Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
740 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
530 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
740 mg/kg
TOXIC EFFECTS :
Behavioral - analgesia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
320 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Gastrointestinal - ulceration or bleeding from stomach
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
395 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
620 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
495 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
1690 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12 gm/kg/30D-C
TOXIC EFFECTS :
Liver - changes in liver weight Endocrine - changes in thymus weight Blood - hemorrhage
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
32760 mg/kg/26W-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from large intestine Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 mg/kg/4D-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12 gm/kg/30D-C
TOXIC EFFECTS :
Gastrointestinal - other changes Blood - normocytic anemia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1300 mg/kg/2W-I
TOXIC EFFECTS :
Liver - other changes Liver - changes in liver weight Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
480 mg/kg/30D-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9 gm/kg/90D-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
840 mg/kg
SEX/DURATION :
female 8-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - other effects to embryo
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
female 3-5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intrauterine
DOSE :
2 mg/kg
SEX/DURATION :
female 4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
DOSE :
270 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
DOSE :
891 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
DOSE :
1 gm/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 4 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
DOSE :
810 mg/kg
SEX/DURATION :
male 60 day(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
DOSE :
8100 mg/kg
SEX/DURATION :
male 60 day(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
420 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1260 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
270 mg/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 393,123,1997 *** REVIEWS *** TOXICOLOGY REVIEW JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 30,23,1992 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4905 No. of Facilities: 82 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 2249 (estimated) No. of Female Employees: 1246 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R51/53;R63
Safety Phrases S36-S61-S36/37
RIDADR 2811
WGK Germany 3
RTECS MU6640000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2924299090

 Synthetic Route

 Customs

HS Code 2916392000
Summary 2916392000 2-(4-isobutylphenyl)propanoic acid。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。Lowest tariff:6.5%。General tariff:30.0%

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 Synonyms

Inoven
Lebrufen
(RS)-ibuprofen
IP-82
Dolgit
Ibumetin
Femadon
2-(4-Isobutylphenyl)propionic acid
QVY1&R D1Y1&1
Para-Isobutylhydratropic Acid
rufen
EINECS 239-784-6
Dolgin
rufin
Ibuprofen
Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-
(±)-ibuprofen
Novogent N
Ibutid
fenbid
2-(4-Isobutylphenyl)propanoic acid
MOTRIN
Andran
Bluton
Dolgirid
4-Isobutyl-α-methylphenylacetic Acid
Amibufen
MFCD00010393
Nurofen
Racemic ibuprofen
Advil
Brufen
Dolo-Dolgit
Seclodin
UNII:WK2XYI10QM
IbU
Panafen
Adran
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