Naproxen

Iupac Name：(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

Molecular Weight：230.263

Modify Date.: 2023-03-06 09:38

Introduction: It is a non-steroidal anti-inflammatory drug for the relief of fever and inflammation and pain associated with arthritis or other symptoms , it has anti-inflammatory, antipyretic and analgesic effects. Naproxen plays a role by inhibiting the cyclooxygenase, which generates prostaglandin and is one kind of enzymes related to inflammatory mediators . It is recommended to take the drug during meals to reduce stomach irritation. View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: Naproxen
1.2 Synonyms: ()-2-(methoxy-2-naphthyl)-propionicacid ()-2-(methoxy-2-naphthyl)-propionsaeure ()-propionicaci (+)-(S)-Naproxen (+)-2-(Methoxy-2-naphthyl)-propionic acid (+)-2-(methoxy-2-naphthyl)-propionicacid (+)-2-(Methoxy-2-naphthyl)-propionsaeure (+)-2-naphthaleneaceticaci (+)-6-Methoxy-alpha-methyl-2-napthaleneacetic acid (+)-NAPROXEN (2S)-2-(6-Methoxy-2-naphthyl)propanoate (2S)-2-(6-Methoxy-2-naphthyl)propanoic acid (2S)-2-(6-Methoxynaphth-2-yl)propanoic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoate (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid (S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid (S)-(+)-Naproxen (S)-naproxen 2-naphthaleneacetic acid, 6-methoxy-a-methyl-, (aS)- 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (S)- 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (αS)- 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, ion(1-), (αS)- ALEVE Anaprox Apronax EINECS 244-838-7 Equiproxen MFCD00010500 NAPRELAN Naprosyn Naprosyne naproxen(1-) Naproxene Naproxeno Naproxenum piproxen

1.3 CAS No.: 22204-53-1

1.4 CID: 156391

1.5 EINECS(EC#): 244-838-7; 247-485-7

1.6 Molecular Formula: C14H14O3 (isomer)

1.7 Inchi: InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1

1.8 InChkey: CMWTZPSULFXXJA-VIFPVBQESA-N

1.9 Canonical Smiles: CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O

1.10 Isomers Smiles: C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O

2. Properties

2.1 Density: 1.197

2.1 Melting point: 153-154℃

2.1 Boiling point: 403.9°Cat760mmHg

2.1 Refractive index: 67.5 ° (C=1, CHCl3)

2.1 Flash Point: 154.5°C

2.1 Precise Quality: 230.09400

2.1 PSA: 46.53000

2.1 logP: 3.03650

2.1 AnalyticLaboratory Methods: Analyte: naproxen;; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards

2.2 Appearance: Solid

2.3 Storage: Ambient temperatures.

2.4 Color/Form: Powder

2.5 Decomposition: When heated to decomposition it emits acrid smoke and fumes.

2.6 Odor: Practically odorless

2.7 Physical: Solid

2.8 pKa: pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain)

2.9 Water Solubility: Insoluble in water.

2.10 Spectral Properties: Specific optical rotation: +66 deg at 25 deg C/D (in chloroform)

2.11 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such a osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 89 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 89 companies. For more detailed information, please visit ECHA C&L website

Of the 20 notification(s) provided by 88 of 89 companies with hazard statement code(s):

H301 (44.32%): Toxic if swallowed [Danger Acute toxicity, oral]
H302 (56.82%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (10.23%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (46.59%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H412 (42.05%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Methods of Manufacturing: Using 2-naphthol through methylation and acetylation to obtain 6-methoxy-2-naphthyl ethyl ketone, then condensed with chloroacetate, and then subjected to isomerization, hydrolysis, oxidation, neutralization, resolution and other reactions be made of.

3.4 Usage: It is a non-steroidal anti-inflammatory drug for the relief of fever and inflammation and pain associated with arthritis or other symptoms , it has anti-inflammatory, antipyretic and analgesic effects. Naproxen plays a role by inhibiting the cyclooxygenase, which generates prostaglandin and is one kind of enzymes related to inflammatory mediators . It is recommended to take the drug during meals to reduce stomach irritation.

4. Safety and Handling

4.1 Symbol: GHS06;

4.1 Hazard Codes: Xn

4.1 Signal Word: DANGER

4.1 Risk Statements: R22

4.1 Safety Statements: S36/37

4.1 Exposure Standards and Regulations: Naproxen granules. ... Conditions of use -- (1) Horses. The drug is used for the relief of inflammation and associated pain and lameness exhibited with arthritis, as well as myositis and other soft tissue diseases of the musculoskeletal system of the horse. (2)(i) For oral maintenance therapy following initial intravenous dosage ... (3) Not for use in horses intended for food. (4) Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Naproxen for injectiion. ... Indications for use: For the relief of inflammation and associated pain and lameness exhibited with arthritis, as well as myositis and other soft tissue diseases of the musculoskeletal system of the horse. (3) Limitations: Not for use in horses intended for food. Federal law restricts this drug to use by or on the order of a licensed veterinarian.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl naproxen, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl naproxen sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Naproxen sodium/
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed over-the-counter drug products, incl naproxen sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Naproxen sodium/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Naproxen is included on this list.

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow = 3.18

4.3 Hazard Class: 6.1(b)

4.3 Hazard Declaration: H301

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: UN 2811

4.4 Caution Statement: P301 + P310

4.4 Formulations/Preparations: Naproxen Preparations Route Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Suspension 125 mg/5 mL Naproxen Suspension (Roxane) Oral Suspension 125 mg/5 mL (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Suspension 125 mg/5 mL Naprosyn (Roche) Oral Tablets 250 mg Naprosyn (Roche) Oral Tablets 250 mg (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets 375 mg Naprosyn (Roche) Oral Tablets 375 mg (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets 500 mg Naprosyn (Roche) Oral Tablets 500 mg (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, delayed-release (enteric-coated) 375 mg EC-Naprosyn (Roche) Oral Tablets, delayed-release (enteric-coated) 375 mg Naproxen Delayed-release Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, delayed-release (enteric-coated) 500 mg EC-Naprosyn (Roche) Oral Tablets, delayed-release (enteric-coated) 500 mg Naproxen Delayed-release Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name)
Naproxen Combination Preparations Route Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Kit 14 tablets, Naproxen 375 mg (Naprosyn) 7 capsules delayed-release (containing enter-coated granules), Lansoprazole, 15 mg (Prevacid) Prevacid NapraPAC 375 (TAP Pharmaceuticals) Oral Kit 14 tablets, Naproxen 500 mg (Naprosyn) 7 capsules delayed-release (containing enter-coated granules), Lansoprazole, 15 mg (Prevacid) Prevacid NapraPAC 500 (TAP Pharmaceuticals)
Naproxen Sodium Preparations Route Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Tablets 220 mg (equivalent to naproxen 200 mg) Aleve Caplets (Bayer) Oral Tablets 220 mg (equivalent to naproxen 200 mg) Aleve Tablets (Bayer) Oral Tablets 220 mg (equivalent to naproxen 200 mg) (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, extended-release 412.5 mg (equivalent to 375 mg naproxen) Naprelan (Carnrick) Oral Tablets, extended-release 412.5 mg (equivalent to 375 mg naproxen) (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, extended-release 550 mg (equivalent to 500 mg naproxen) Naprelan (Carnrick Oral Tablets, extended-release 550 mg (equivalent to 500 mg naproxen) (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, film-coated 275 mg (equivalent to naproxen 250 mg) Anaprox (Roche) Oral Tablets, film-coated 275 mg (equivalent to naproxen 250 mg) (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, film-coated 550 mg (equivalent to naproxen 500 mg) Anaprox DS, scored (Roche) Oral Tablets, film-coated 550 mg (equivalent to naproxen 500 mg) (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name)
Naproxen Sodium Combination Preparations Route Dosage Form Strength Brqand or Generic Name (Manufacturer) Oral Tablets, extended release 220 mg (equivalent to 200 mg naproxen) with Pseudoephedrine Hydrochloride 120 mg Aleve Cold and Sinus (Roche)

4.5 WGK Germany: 3

4.5 RTECS: UF5275000

4.5 Safety: Safety Information of?(+)-2-(Methoxy-2-naphthyl)-propionic acid (CAS NO.22204-53-1):
Hazard Codes: Xn?
Risk Statements: 22
22: Harmful if swallowed??
Safety Statements: 36/37
36/37: Wear suitable protective clothing and gloves
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: UF5275000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous, and intravenous routes. Human systemic effects: acute renal failure, acute tubular necrosis, cholestatic jaundice, dermatitis, diarrhea, excitement, fever, hypermotility, interstitial nephritis, nausea or vomiting. Human teratogenic effects by ingestion: developmental abnormalities of the cardiovascular (circulatory) system, respiratory system, gastrointestinal system, and other developmental abnormalities. Human reproductive effects by ingestion (effects on newborn): change in condition of newborn at birth, biochemical and metabolic effects, and other neonatal measures or effects. Human mutation data reported. An anti-inflammatory, analgesic and antipyretic. An FDA proprietary drug. When heated to decomposition it emits acrid smoke and irritating fumes.

4.6 Toxicity: Oral-Rat? LD50 248? mg/kg; Oral-Mouse LD50: 360 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

22204-53-1Total: 25 Synthesis Route

92455-03-3

22204-53-1 378 Suppliers

Literatures:
Nagasawa, Kazuo; Yoshitake, Shinji; Amiya, Takao; Ito, Keiichi Synthetic Communications, 1990 , vol. 20, # 13 p. 2033 - 2040
Yield: ~81%

23981-47-7 21 Suppliers

22204-53-1 378 Suppliers

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

23981-80-8 53 Suppliers

22204-53-1 378 Suppliers

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

View all

8. Precursor and Product

precursor:

31220-35-6

23981-47-7

75-09-2

616-38-6

201230-82-2

63444-51-9

107951-72-4

62784-66-1

362523-40-8

878194-08-2

32305-59-2

27602-79-5

748801-45-8

119408-04-7

52344-67-9

1220907-01-6

26159-36-4

27854-88-2

108781-65-3

54656-96-1

67-56-1

23981-80-8

92455-03-3

134435-65-7

30012-51-2

View all

product :

26159-34-2

23981-80-8

1262956-64-8

26159-35-3

7440-44-0

26159-36-4

52079-10-4

32725-05-6

125836-70-6

84236-26-0

41945-43-1

9. Other Information

9.0 Merck: 14,6417

9.1 BRN: 3591067

9.2 Non-steroidal anti-inflammatory drugs: Naproxen is a non-steroidal anti-inflammatory drug ,it is a PG synthase inhibitor, which can inhibit prostaglandin synthetase, it has significant analgesic and antipyretic effects, oral absorption is rapid and complete, 2 to 4 hours after a dose ,plasma concentration reaches the peak, in the blood , more than 99% is bound to plasma proteins, t1/2 is 13 to 14 hours, about 95% is discharged from the urine with the prototype and metabolites.it is clinically used For the treatment of rheumatic and rheumatoid arthritis , osteoarthritis, ankylosing spondylitis, gout, arthritis, tenosynovitis.it can also be used to alleviate pain caused by musculoskeletal sprains, contusions,damages and dysmenorrhea . But it should be noted that like other non-steroidal anti-inflammatory drugs, the same serious gastrointestinal adverse reactions could occur at any time while taking naproxen during treatment, so the active gastroduodenal ulcer patients are hanged, other gastrointestinal tract disease patients should take this drug under close medical supervision.

9.3 Chemical Properties: White crystal or crystalline powder. Melting point 155.3 ℃. Soluble in acetone, soluble in methanol, ethanol, acetic acid, insoluble in benzene, practically insoluble in water. In case of light,it is color-graded, odorless, tasteless.

9.4 Uses: It is a non-steroidal anti-inflammatory drug for the relief of fever and inflammation and pain associated with arthritis or other symptoms , it has anti-inflammatory, antipyretic and analgesic effects. Naproxen plays a role by inhibiting the cyclooxygenase, which generates prostaglandin and is one kind of enzymes related to inflammatory mediators . It is recommended to take the drug during meals to reduce stomach irritation.

9.5 Used in Particular Diseases: Acute Gouty Arthritis:
Dosage and Frequency: 500 mg twice daily for 3 days, then 250–500 mg daily for 4–7 days

9.6 production method: by methylation, acetylation With 2-naphthol , 6-methoxy-2-acetonaphthone is produced, then it is condensed with acid ester, then generate the product through isomerization, hydrolysis, oxidation, and split and other reactions.

9.7 Category: Toxic substances

9.8 Toxicity grading: Highly toxic

9.9 Acute toxicity: Oral-rat LD50 248 mg/kg; Oral-Mouse LD50: 360 mg/kg

9.10 Flammability and hazard characteristics: Combustible; combustion produces toxic and acrid smoke.

9.11 Storage Characteristics: Ventilated, low-temperature ,dry storeroom, it should be stored and transported from food raw materials separately.

9.12 Extinguishing agent: Water, dry powder, foam,sand

9.13 Description: Naproxen is synthesized from 2-methoxynaphthalene and the (+)-isomer obtained by resolution with cinchonidine (61). It was introduced in the United States in 1976 and, as a generic drug, has consistently been among the more popular NSAIDs. It is marketed as the S-(+)-enantiomer, but interestingly, the sodium salt of the (–)-isomer also is on the market as Anaprox. As an inhibitor of prostaglandin biosynthesis, it is 12 times more potent than aspirin, 10 times more potent than phenylbutazone, three to four times more potent than ibuprofen, and four times times more potent than fenoprofen, but it is approximately 300 times less potent than indomethacin.

9.14 Chemical Properties: white to light yellow crystal powde

9.15 Originator: Naprosyn,Syntex,UK,1973

9.16 Uses: An anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory

9.17 Uses: Being analogous to other drugs of this series, naproxene exhibits analgesic, fever-reducing, and long-lasting anti-inflammatory action. It causes reduction and removal of painful symptoms including joint pain, stiffness, and swelling in the joints. It is used in the same indications as ibuprofen.

9.18 Definition: ChEBI: A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such a osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.

9.19 Indications: Naproxen (Naprosyn) also has pharmacological properties and clinical uses similar to those of ibuprofen. It exhibits approximately equal selectivity for COX-1 and COX-2 and is better tolerated than certain NSAIDs, such as indomethacin. Adverse reactions related to the GI tract occur in about 14% of all patients, and severe GI bleeding has been reported. CNS complaints (headache, dizziness, drowsiness), dermatological effects (pruritus, skin eruptions, echinoses), tinnitus, edema, and dyspnea also occur.

9.20 Manufacturing Process: According to US Patent 3,658,858, a solution of 24 grams of 2-bromo-6- methoxynaphthalene in 300 ml of tetrahydrofuran is slowly added to 2.5 grams of magnesium turnings and 100 ml of tetrahydrofuran at reflux temperature. After the addition is complete, 20 grams of cadium chloride is added, and the resultant mixture is refluxed for 10 minutes to yield a solution of di-(6-methoxy-2-naphthyl)cadmium (which can be separated by conventional chromatography, although separation is unnecessary).
A solution of 18 grams of ethyl 2-bromopropionate in 20 ml of tetrahydrofuran is then added to the cooled reaction mixture. After 24 hours at 20°C, the product is hydrolyzed by adding 200 ml of 5 weight percent methanolic sodium hydroxide followed by heating to reflux for 1 hour. The reaction mixture is then diluted with excess 1 N sulfuric acid and extracted with ether. The ether phase is separated, evaporated to dryness and the residue is recrystallized from acetone-hexane to yield 2-(6-methoxy-2- naphthyl)propionic acid.

9.21 Brand name: Naprosyn (Roche).

9.22 Therapeutic Function: Antiinflammatory

9.23 Synthesis Reference(s): Tetrahedron, 49, p. 8433, 1993 DOI: 10.1016/S0040-4020(01)81926-8

9.24 General Description: Naproxen (Naprosyn, Anaprox), marketed as the (S)-enantiomer,is well absorbed after oral administration, givingpeak plasma levels in 2 to 4 hours and a half-life of 13 hours.Naproxen is highly protein bound and displaces most protein-bound drugs. It is recommended for use in RA, OA, acute gouty inflammation, and in primary dysmenorrhea. Itshows good analgesic activity (i.e., 400 mg is comparable to75–150 mg of oral meperidine and superior to 65 mg ofpropoxyphene and 325 mg of aspirin plus 30 mg of codeine).It is also available OTC as 200-mg tablets (Aleve).

9.25 Pharmacokinetics: Naproxen is almost completely absorbed following oral administration. Peak plasma levels are achieved within 2 to 4 hours following administration. Like most of the acidic NSAIDs (pKa = 4.2), it is highly bound (99.6%) to plasma proteins. Approximately 70% of an administered dose is eliminated as either unchanged drug (60%) or as conjugates of unchanged drug (10%). The remainder is converted to the 6-O-desmethyl metabolite by both CYP3A4 and CYP1A2 and, further, to the glucuronide conjugate of the demethylated metabolite. The 6-O-desmethyl metabolite lacks anti-inflammatory activity. Like most of the arylalkanoic acids, the most common side effect associated with the use of naproxen is irritation to the GI tract. The most common other adverse reactions are associated with CNS disturbances (e.g., nausea and dizziness).

9.26 Storage Conditions: Using 2-naphthol through methylation and acetylation to obtain 6-methoxy-2-naphthyl ethyl ketone, then condensed with chloroacetate, and then subjected to isomerization, hydrolysis, oxidation, neutralization, resolution and other reactions be made of.

9.27 Storage features: The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

9.28 Usage: (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid is a non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.

9.29 Clinical Use: Naproxen is indicated for the treatment of rheumatoid arthritis, osteoarthritis, juvenile arthritis, ankylosing spondylitis, tendinitis, bursitis, acute gout, and primary dysmenorrhea and for the relief of mild to moderate pain.

9.30 Chemical Synthesis: Naproxene, 2-(6-methoxy-2-naphthyl)-propionic acid (3.2.15) can be synthesized by the methods of synthesis described for ibuprofen as well as by the methods of fenoprofen (3.2.21) and ketoprofen (3.2.27) synthesis that will be described below from 2-acetyl or 2-chloromethyl-6-methoxynaphthaline [99–101].

9.31 Veterinary Drugs and Treatments: The manufacturer lists the following indications: “…for the relief of inflammation and associated pain and lameness exhibited with myositis and other soft tissue diseases of the musculoskeletal system of the horse.” (Package Insert; Equiproxen?—Syntex). It has also been used as an antiinflammatory/analgesic in dogs for the treatment of osteoarthritis and other musculoskeletal inflammatory diseases (see adverse reactions below).

9.32 Drug interactions: Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia
. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage).
Antibacterials: possibly increased risk of convulsions with quinolones.
Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban.
Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin concentration.
Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir.
Ciclosporin: may potentiate nephrotoxicity
Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib.
Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics.
Lithium: excretion decreased.
Pentoxifylline: increased risk of bleeding.
Probenecid: excretion reduced by probenecid.
Tacrolimus: increased risk of nephrotoxicity.

9.33 Metabolism: Naproxen is extensively metabolised in the liver to 6-0-desmethyl naproxen. Both naproxen and 6-0-desmethyl naproxen are further metabolised to their respective acylglucuronide conjugated metabolites. About 95% of a dose is excreted in urine as naproxen and 6-O-desmethylnaproxen and their conjugates. Less than 5% of a dose appears in the faeces.

10. Computational chemical data

Molecular Weight: 230.263g/mol
Molecular Formula: C₁₄H₁₄O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 230.094294304
Monoisotopic Mass: 230.094294304
Complexity: 277
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 46.5
Heavy Atom Count: 17
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAADBUAAAGgAACAAADQSAmAIyDsAABgCIAiDSCAACCAAgIAAIiAEGCIgMJjKENRqAcCAkwBEIqAeIyPCO4AADAAAQAADAAAYAACAAAAAAAAAAAA==

11. Recommended Suppliers

Global365SuppliersView all >>

Hebei Crovell Biotech Co. Ltd Diamond member

-120YR

Products:Cosmetic Raw Materials,solvents,etc.
Tel:86-311-66562153
Email:breeduan@crovellbio.com

Naproxen Cas 22204-53-1 from China

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kilogram
Time: 2023/06/06

Inquire

Hebei Bester Biotechnology Co., Ltd. Diamond member

-121YR

Products:pmk powder ;pmk oil ;bmk powder ;bmk oil ;Protonitazene hcl ; Bromazolam ; Metonitazene; 2-Bromo-4'-methylpropiophenone ;
Tel:+86-180-32431584
Email:amy@chbbest.com

CAS 22204-53-1 Naproxen

Purity:99%Packing: 200kg/bag FOB
Price: 1 USD/kg
Time: 2023/06/06

Inquire

Hanhong Medicine Technology (Hubei) Co., Ltd. Diamond member

-120YR

Products:5413-05-8 Ethyl 2-phenylacetoacetate; 20320-59-6/5449-12-7 BMK powder; 28578-16-7 Pmk glycidate; 79099-07-3 N-BOC-4-piperidone; 49851-31-2 2-bromo-1-phenylpentan-1-one; 288573-56-8
Tel:86-27-18672957835
Email:aimee@hanhong-api.com

Factory Direct Selling: Naproxen CAS 22204-53-1 99% Purity White Powder Hanhong Free Sample

Purity:99%Packing: 200kg/bag FOB
Price: 0.5 USD/gram
Time: 2023/06/06

Inquire

Hebei Yinsheng Technology Co., Ltd. Diamond member

-121YR

Products:Hebei Yinsheng Technology Co., Ltd is a company dedicated to the research and development, production and sales of organic compounds, pharmaceutical intermediates and chemical raw materials
Tel:0086-03113-17331136691
Email:lemon@hbyinsheng.com

Naproxen Cas 22204-53-1 from China(whatsapp:+8617331136198)