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22204-53-1

22204-53-1 structure
22204-53-1 structure
Name naproxen
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
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
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

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
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
92455-03-3 structure

92455-03-3

~81%

22204-53-1 structure

22204-53-1

Literature: Nagasawa, Kazuo; Yoshitake, Shinji; Amiya, Takao; Ito, Keiichi Synthetic Communications, 1990 , vol. 20, # 13 p. 2033 - 2040
23981-80-8 structure

23981-80-8

~%

22204-53-1 structure

22204-53-1

Literature: Harrison; Lewis; Nelson; Rooks; Roszkowski; Tomolonis; Fried Journal of medicinal chemistry, 1970 , vol. 13, # 2 p. 203 - 205
23981-47-7 structure

23981-47-7

~%

22204-53-1 structure

22204-53-1

Literature: Harrison; Lewis; Nelson; Rooks; Roszkowski; Tomolonis; Fried Journal of medicinal chemistry, 1970 , vol. 13, # 2 p. 203 - 205
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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title: CAS No. 22204-53-1 | Chemsrc address: https://www.chemsrc.com/en/baike/311656.html

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