CAS 22204-53-1|Naproxen
Introduction：Basic information about CAS 22204-53-1|Naproxen, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | ChineseUSA | Flash Point | 154.5±15.3 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | naproxen |
|---|---|
| Synonym | More Synonyms |
Naproxen BiologicalActivity
| 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 >>AutophagyResearch 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. |
Chemical & Physical Properties
| 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 |
| InChIKey | CMWTZPSULFXXJA-VIFPVBQESA-N |
| SMILES | COc1ccc2cc(C(C)C(=O)O)ccc2c1 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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)
Safety Information
| 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 |
Customs
| 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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Synonyms
| Equiproxen |
| piproxen |
| (+)-(S)-Naproxen |
| (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid |
| (2S)-2-(6-Methoxy-2-naphthyl)propanoic acid |
| 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (S)- |
| 2-naphthaleneacetic acid, 6-methoxy-a-methyl-, (aS)- |
| Naproxen |
| Apronax |
| Naprosyne |
| Naproxene |
| (+)-NAPROXEN |
| (S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid |
| ALEVE |
| (S)-naproxen |
| Anaprox |
| (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid |
| Naproxeno |
| 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (αS)- |
| NAPRELAN |
| Naproxenum |
| MFCD00010500 |
| (2S)-2-(6-Methoxynaphth-2-yl)propanoic acid |
| EINECS 244-838-7 |
| (S)-(+)-Naproxen |
| Naprosyn |
