Naproxen

Modify Date: 2024-01-02 19:04:05

Naproxen structure	Common Name	Naproxen
	CAS Number	22204-53-1	Molecular Weight	230.259
	Density	1.2±0.1 g/cm3	Boiling Point	403.9±20.0 °C at 760 mmHg
	Molecular Formula	C₁₄H₁₄O₃	Melting Point	152-154 °C(lit.)
	MSDS	Chinese USA	Flash Point	154.5±15.3 °C
	Symbol	GHS06	Signal Word	Danger

Use of Naproxen

Naproxen is a COX-1 and COX-2 inhibitor with IC50s of 8.72 and 5.15 μM, respectively in cell assay.

Name	naproxen
Synonym	More Synonyms

Description	Naproxen is a COX-1 and COX-2 inhibitor with IC50s of 8.72 and 5.15 μM, respectively in cell assay.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Inflammation/Immunology
Target	COX-2:5.65 μM (IC50) COX-1:9.55 μM (IC50)
In Vitro	Naproxen etemesil is a lipophilic, non-acidic, inactive prodrug of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a well known nonsteroidal anti-inflammatory drug. Naproxen is approximately equipotent inhibitor of COX-1 and COX-2 in intact cells with IC50s of 2.2 μg/mL and 1.3 μg/mL, respectively[1].
In Vivo	Naproxen exerts an anti-inflammatory and antifibrotic effect in mouse model of bleomycin-induced lung fibrosis. Naproxen also downregulates TGF-β levels and Smad3/4 complex formation[2]. Naproxen is shown to inhibit the time-courses of pain, fever and PGE2 with similar potencies (IC50=27, 40, 13 μM)[3].
Cell Assay	BAEC are incubated for 30 min with Naproxen (0.1 ng/mL to 1 mg/mL). Arachidonic acid (30 μM) is then added, and the cells are incubated for a further 15 min at 37°C. The medium is then removed, and radioimmunoassay is used to measure the formation of 6-keto-PGF,a, PGE2, thromboxane B2, or PGF2a[1].
Animal Admin	Rats[3] To measure the analgesic effects of naproxen in a carrageenaninduced model of monoarthritis, Male Sprague–Dawley rats (n=48, 217±28 g) are randomly divided into four groups of 12 by an internally developed computer program, allowing the blind performance of the behavioral experiment. To induce hyperalgesia by inflammation, animals in groups 1B, 1C, and 1D receive a 40-μL intra-articular injection of a saline solution containing 7.5 mg/mL carrageenan in the left hind limb under isoflurane anesthesia (time=−1 h). Animals in group 1A receive no injection. After 1 h (time=0) the animals in groups 1A, 1B, 1C, and 1D receive oral doses of naproxen in saline of 0, 0, 7.5 and 30 μmol/kg, respectively. The doses and time points of measurements are selected on the basis of simulations predicting measuring a full concentration-effect relationship within the time-span of the experiment[3]. Mice[2] Bleomycin (0.05 IU) is instilled intratracheally to C57BL/6 mice, which are then treated by micro-osmotic pump with vehicle, JNJ7777120 (40 mg/kg b.wt.), naproxen (21 mg/kg b.wt.), or a combination of both. Airway resistance to inflation, an index of lung stiffness, is assessed, and lung specimens are processed for inflammation, oxidative stress, and fibrosis markers[2].
References	[1]. Mitchell JA, et al. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11693-7. [2]. Rosa AC, et al. Prevention of bleomycin-induced lung inflammation and fibrosis in mice by naproxen and JNJ7777120 treatment. J Pharmacol Exp Ther. 2014 Nov;351(2):308-16. [3]. Krekels EH, et al. Pharmacokinetic-pharmacodynamic modeling of the inhibitory effects of naproxen on the time-courses of inflammatory pain, fever, and the ex vivo synthesis of TXB2 and PGE2 in rats.

Density	1.2±0.1 g/cm3
Boiling Point	403.9±20.0 °C at 760 mmHg
Melting Point	152-154 °C(lit.)
Molecular Formula	C₁₄H₁₄O₃
Molecular Weight	230.259
Flash Point	154.5±15.3 °C
Exact Mass	230.094299
PSA	46.53000
LogP	3.00
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.609

Naproxen MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UF5275000

CHEMICAL NAME :: Propionic acid, 2-(6-methoxy-2-naphthyl)-, (+)-

CAS REGISTRY NUMBER :: 22204-53-1

LAST UPDATED :: 199801

DATA ITEMS CITED :: 33

MOLECULAR FORMULA :: C14-H14-O3

MOLECULAR WEIGHT :: 230.28

WISWESSER LINE NOTATION :: L66J CY1&VQ HO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 315 mg/kg/3W-I

TOXIC EFFECTS :: Behavioral - excitement Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 3429 mg/kg/35W-I

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section Lungs, Thorax, or Respiration - cyanosis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 126 mg/kg/3W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - dyspnea Blood - eosinophilia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 2250 mg/kg/26W-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 900 mg/kg/9W-I

TOXIC EFFECTS :: Skin and Appendages - photosensitivity (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 40 mg/kg/2D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 70 mg/kg/W-I

TOXIC EFFECTS :: Liver - jaundice, cholestatic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 50 mg/kg/7D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 248 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 :: 354 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 928 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 360 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 - mouse

DOSE/DURATION :: 500 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 435 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1234 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 - dog

DOSE/DURATION :: >1 gm/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 :: Unreported

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1 gm/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 - guinea pig

DOSE/DURATION :: 665 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 :: 1400 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 :: Unreported

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 4110 mg/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 :: 20 mg/kg/4D-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 :: 970 mg/kg/17D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from small intestine Blood - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 30 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - respiratory system Reproductive - Specific Developmental Abnormalities - gastrointestinal system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 30 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - Apgar score (human only) Reproductive - Effects on Newborn - other neonatal measures or effects Reproductive - Effects on Newborn - biochemical and metabolic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 120 mg/kg

SEX/DURATION :: female 28 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Specific Developmental Abnormalities - respiratory system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 6 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

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 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6164 No. of Facilities: 16 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 444 (estimated) No. of Female Employees: 260 (estimated)

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R22
Safety Phrases	S36/37
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	UF5275000
Packaging Group	III
Hazard Class	6.1(b)
HS Code	2916399090

N/A

CAS#:92455-03-3

~81%

Naproxen

CAS#:22204-53-1

Literature: Nagasawa, Kazuo; Yoshitake, Shinji; Amiya, Takao; Ito, Keiichi Synthetic Communications, 1990 , vol. 20, # 13 p. 2033 - 2040

2-(6-Methoxynap...

CAS#:23981-80-8

Naproxen

CAS#:22204-53-1

Literature: Harrison; Lewis; Nelson; Rooks; Roszkowski; Tomolonis; Fried Journal of medicinal chemistry, 1970 , vol. 13, # 2 p. 203 - 205

2-(6-Methoxynap...

CAS#:23981-47-7

Naproxen

CAS#:22204-53-1

Literature: Harrison; Lewis; Nelson; Rooks; Roszkowski; Tomolonis; Fried Journal of medicinal chemistry, 1970 , vol. 13, # 2 p. 203 - 205

Precursor 2
CAS#:23981-80-8 2-(6-Methoxynap... CAS#:23981-47-7 2-(6-Methoxynap...
DownStream 10
CAS#:51091-84-0 (S)-(+)-Naproxe... CAS#:3900-45-6 2-Acetyl-6-meth... CAS#:52079-10-4 O-Desmethylnaproxen CAS#:7440-44-0 Carbon
CAS#:23981-80-8 2-(6-Methoxynap... CAS#:32725-05-6 2-Naphthaleneet... CAS#:125836-70-6 naproxen isocyanate CAS#:1262956-64-8 NCX 466
CAS#:26159-34-2 naproxen sodium CAS#:163133-43-5 Naproxcinod

HS Code	2918990090
Summary	2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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4-O-methylhonokiol (MH) is known to inhibit inflammation by partially understood mechanisms. Here, the anti-inflammatory mechanisms of MH were examined using enzymatic, cellular, and animal assays. In...

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