Naproxen
- CAS No.
- 22204-53-1
- Chemical Name:
- Naproxen
- Synonyms
- NAPROXEN BASE;(S)-NAPROXEN;(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid;Naprosyn;NAPROXENE;NAPROXEN FREE BASE;axer;Bonyl;Xenar;Naxen
- CBNumber:
- CB8274937
- Molecular Formula:
- C14H14O3
- Molecular Weight:
- 230.26
- MOL File:
- 22204-53-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/13 17:19:14
| Melting point | 152-154 °C (lit.) |
|---|---|
| alpha | D +66° (in chloroform) |
| Boiling point | 332.25°C (rough estimate) |
| Density | 1.1450 (rough estimate) |
| refractive index | 67.5 ° (C=1, CHCl3) |
| Flash point | 9℃ |
| storage temp. | 2-8°C |
| solubility | Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol. |
| form | powder |
| pka | pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain) |
| color | White to Almost white |
| optical activity | [α]25/D +66°, c = 1 in chloroform |
| Water Solubility | Insoluble in water. |
| Merck | 14,6417 |
| BRN | 3591067 |
| BCS Class | 2 |
| LogP | 3.18 |
| CAS DataBase Reference | 22204-53-1(CAS DataBase Reference) |
| NIST Chemistry Reference | Naproxen(22204-53-1) |
| EPA Substance Registry System | 2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (.alpha.S)- (22204-53-1) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS07,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335-H361fd-H411 | |||||||||
| Precautionary statements | P202-P273-P301+P312-P302+P352-P305+P351+P338-P308+P313 | |||||||||
| Hazard Codes | Xn,T,F | |||||||||
| Risk Statements | 22-39/23/24/25-23/24/25-11-36/37/38 | |||||||||
| Safety Statements | 36/37-45-16-7-26 | |||||||||
| RIDADR | UN 2811 6.1/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UF5275000 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29189900 | |||||||||
| Toxicity | LD50 in mice (mg/kg): 435 i.v.; 1234 orally; in rats (mg/kg): 575 i.p.; 534 orally (Roszkowski) | |||||||||
| NFPA 704 |
|
Naproxen price More Price(11)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | PHR1040 | Naproxen Pharmaceutical Secondary Standard; Certified Reference Material | 22204-53-1 | 500MG | ₹10792.53 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | N8280 | Naproxen meets USP testing specifications | 22204-53-1 | 5G | ₹9417.75 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | N-042 | Naproxen solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? | 22204-53-1 | 1ML | ₹3311.7 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 284785 | (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid 98% | 22204-53-1 | 5G | ₹6733.15 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 46482 | Naproxen VETRANAL?, analytical standard | 22204-53-1 | 250MG | ₹8270.3 | 2022-06-14 | Buy |
Naproxen Chemical Properties,Uses,Production
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.
Chemical Properties
white to light yellow crystal powde
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.
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.
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.
brand name
Naprosyn (Roche), Anaprox (Syntex, Canada, USA), Apranax (Roche, France), Bonyl (Ercopharm, Denmark), Miranax (Syntex, Finland), Novo-Naprox (Novorpharm, Canada), Proxen (Hoffmann La Roche, Germany).
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).
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).
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.
Side effects
Common side effects of Naproxen may include indigestion, heartburn, stomach pain, nausea, headache, dizziness, drowsiness, bruising, itching, rash, swelling, or ringing in the ears. Seek immediate medical attention if you have any of the following serious drug reactions. For example: shortness of breath, swelling or rapid weight gain, rash, signs of stomach bleeding (bloody or tarry stools, coughing up blood or vomit that looks like coffee grounds), liver problems (nausea, upper stomach pain, itching, feeling tired, flu-like symptoms, loss of appetite, dark urine, clay-coloured stools, jaundice), kidney problems (little or no urination, pain or difficulty in urinating, swelling of the feet or ankles, feeling tired or shortness of breath), low red blood cells (anaemia), etc. In addition, in rare cases, a severe allergic reaction to naproxen may occur. You may also suffer from stomach ulcers and other adverse reactions when taking it for a long time.
Synthesis
Synthesis of Naproxene: Friedel - Crafts acylation (aluminum chloride - nitrobenzene) of β-naphthol methyl ether affords 2-acetyl-6-
methoxynaphthalene, which, when treated
with either dimethylsulfonium or dimethylsulfoxonium methylide, gives 2-(6-methoxynaphthalen-2-yl)propylene oxide. Treatment of the latter with boron trifluoride etherate in
tetrahydrofuran gives 2-(6-methoxynaphthalen-
2-yl)propionaldehyde, which is oxidized using Jones reagent (4 M chromic acid) to
yield the racemic 2-(6-methoxynaphthalen-2-
yl)propionic acid. Resolution and isolation of
the dextrorotatory enantiomer is accomplished
via its cinchonidine salt.
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].
Naproxen Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| ANWITA APIS | +919000311012 | Hyderabad, India | 198 | 58 | Inquiry |
| Dr. Reddy's Laboratories Ltd | +91-4049002900 +91-4049002900 | Hyderabad, India | 165 | 58 | Inquiry |
| SynThink RESEARCH CHEMICALS | +91-8177860948 +91-8177860948 | Mumbai, India | 494 | 58 | Inquiry |
| AnalyticsStanza Inc | +91-7032031309 +91-7032031309 | Hyderabad, India | 227 | 58 | Inquiry |
| Divis Laboratories Ltd | +91-4066966413 +91-4066966413 | Hyderabad, India | 34 | 58 | Inquiry |
| Alfa Omega Pharma | +91-8050045945 +91-9972665399 | Maharashtra, India | 126 | 58 | Inquiry |
| Vishrudh laboratories pvt ltd | +91-9666132889 +91-8097369002 | Telangana, India | 117 | 58 | Inquiry |
| Aspen Biopharma Labs Pvt Ltd | +91-9248058660 +91-9248058662 | Telangana, India | 234 | 58 | Inquiry |
| Alfa-Omega Pharma | 08080929094 | Karnataka, India | 73 | 58 | Inquiry |
| Shivam Pharma Chemicals | 91-22-26403900 | Maharashtra, India | 656 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| ANWITA APIS | 58 |
| Dr. Reddy's Laboratories Ltd | 58 |
| SynThink RESEARCH CHEMICALS | 58 |
| AnalyticsStanza Inc | 58 |
| Divis Laboratories Ltd | 58 |
| Alfa Omega Pharma | 58 |
| Vishrudh laboratories pvt ltd | 58 |
| Aspen Biopharma Labs Pvt Ltd | 58 |
| Alfa-Omega Pharma | 58 |
| Shivam Pharma Chemicals | 58 |
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