CAS 15687-27-1|Ibuprofen

Introduction：Basic information about CAS 15687-27-1|Ibuprofen, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Ibuprofen BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles403
8. Synonyms

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	ChineseUSA	Flash Point	216.7±14.4 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	ibuprofen
Synonym	More Synonyms

Ibuprofen BiologicalActivity

Description	Ibuprofen is an anti-inflammatory inhibitor targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively.
Related Catalog	Signaling Pathways >>Immunology/Inflammation >>COXResearch Areas >>Infection
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
InChIKey	HEFNNWSXXWATRW-UHFFFAOYSA-N
SMILES	CC(C)Cc1ccc(C(C)C(=O)O)cc1
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
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

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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