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Celecoxib

Indications and Usage Application in Particular Diseases Mechanisms of Action Pharmacokinetics Clinical Research Side Effects Warnings and Precautions
Celecoxib
Celecoxib structure
CAS No.
169590-42-5
Chemical Name:
Celecoxib
Synonyms
YM 177;Celecox;Celebra;SC 58635;celexibn;Celecoxi;CELEBREX;Celocoxib;celexicob;CELECOXIB
CBNumber:
CB7444681
Molecular Formula:
C17H14F3N3O2S
Formula Weight:
381.37
MOL File:
169590-42-5.mol

Celecoxib Properties

Melting point:
157-159°C
storage temp. 
Store at RT
solubility 
DMSO: >20mg/mL
form 
powder
color 
white to off-white
Merck 
14,1956
CAS DataBase Reference
169590-42-5(CAS DataBase Reference)

SAFETY

Hazard Codes  Xn
Risk Statements  20/21/22-52-61-60
Safety Statements  22-24/25-28-37/39
RIDADR  UN 3077 9 / PGIII
WGK Germany  3
RTECS  DB2944937
HazardClass  IRRITANT
HS Code  29350090
Hazardous Substances Data 169590-42-5(Hazardous Substances Data)

Celecoxib price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1683 Celecoxib Pharmaceutical Secondary Standard; Certified Reference Material 169590-42-5 1g $71.1 2018-11-13 Buy
Sigma-Aldrich 1098504 Celecoxib United States Pharmacopeia (USP) Reference Standard 169590-42-5 200mg $348 2018-11-13 Buy
Cayman Chemical 10008672 Celecoxib ≥98% 169590-42-5 50mg $35 2018-11-19 Buy
Cayman Chemical 10008672 Celecoxib ≥98% 169590-42-5 100mg $67 2018-11-19 Buy
Sigma-Aldrich PZ0008 Celecoxib ≥98% (HPLC) 169590-42-5 5mg $91.6 2018-11-20 Buy

Celecoxib Chemical Properties,Uses,Production

Indications and Usage

Celecoxib and Rofecoxib are two currently used COX-2 inhibitors. Successfully developed by GD Searle & Pfizer Co. (U.S.,) released in 1999, trade name: Celebrex.
Celecoxib is a nonsteroidal, anti-inflammatory agent with significant analgesic and anti-inflammatory effects, causing the lowest incidence of upper gastrointestinal tract ulcers and other complications. Used clinically to treat acute and chronic osteoarthritis and rheumatoid arthritis, with an anti-inflammatory analgesic role, relieving the signs and symptoms of osteoarthritis and rheumatoid arthritis.

Application in Particular Diseases

In Osteoarthritis:
As a Cyclooxygenase-2 (COX-2) selective inhibitor, Celecoxib demonstrate analgesic benefits that are similar to traditional nonselective NSAIDs. Although COX-2 selective inhibition was designed to reduce NSAIDinduced gastropathy (e.g., ulcers, bleeding, perforation), concerns about adverse cardiovascular events (e.g., myocardial infarction, stroke) have led authorities to recommend their use only in selected patients who are at high risk for NSAID-related GI effects and low risk for cardiovascular toxicity.

Mechanisms of Action

Celecoxib has the anti-inflammatory and analgesic effect of NSAIDs. Because of its chemical structure, it can be combined with COX-2, selectively inhibiting COX-2. Its phenyl group binds with the hydrophobic channel of COX-2, and its hydrophilic sulfonamide forms a hydrogen chain with 513 arginine and 90 histidine in the COX-2 "side pocket.” It is also in close contact with arginine in the COX-2120 position and plays a role in inhibiting COX-2 from converting arachidonic acid to prostaglandins which are harmful to the human body. Due to subtle differences between the structures of COX-1 and COX-2, Celecoxib cannot enter the COX-1 molecule, nor inhibit its transformation of arachidonic acid into prostaglandins.  Thus, it has good anti-inflammatory and analgesic effects, protects gastric mucosa, protects renal blood flow, regulates platelet aggregation, and resolves the gastric irritation problems of commonly used NSAIDs.

Pharmacokinetics

Celecoxib can be quickly absorbed after oral administration, with peak concentration at about 3h. The peak concentration of a single oral dose of 200 mg is 705 ng/ml. After absorption, up to 97% binds to plasma proteins; the drug is widely distributed, with apparent volume of distribution (455±166)L. Metabolized in vivo through P450(CYP)2C9 liver enzyme metabolism. Combined with carboxylic acid and glucuronide through biotransformation, about 2% of original amount excreted in urine and feces. Half-life about 1h.
Drug disposition and pharmacokinetics vary with race and age, amplifying total mild liver absorption damage (AUC.) When ingested with high fat peak plasma concentration effects are extended 1-2h, and AUC increases 10%-20%. When taken with aluminum and magnesium antacids peak concentration is reduced 37%, and AUC decreases 10%. No interaction with warfarin, ketoconazole, or methotrexate (MTX.) Clinically significant interactions with fluconazole and lithium, reducing Cmax 37% and AUC 10%。

Clinical Research

50 Clinical trials on more than 130,000 subjects in 23 countries have been conducted on Celecoxib. Regarding anti-inflammatory and analgesic effects towards osteoarthritis (OA) and rheumatoid arthritis (RA): subjects ages 18-93 had been diagnosed with OA or RA for at least three months, and the disease was in an active or relapsed state. Diagnoses were made according to the criteria of the American College of Rheumatology (ACR.) Visual analog scales (VAS) and American Pain Society (APS) test tables were used to evaluate joint pain, and the WOMAC and health assessment questionnaire (HAQ) impaired function indices were used to evaluate joint pain, stiffness, and function loss. Extensive clinical trials have shown that Celecoxib is effective against OA and RA joint pain.
Clinical trials on the efficacy of Celecoxib against OA have concluded: by VAS evaluation, 100 and 200 mg bid have the same effect on reducing signs and symptoms of OA as with 500 mg bid of naproxen, greater than with placebos, although the effects of 200 mg bid are not significantly greater than those with 100 mg bid. The effects on OA pain last 24-48h, equivalent to 500 mg bid of naproxen. Using the WOMAC (pain, joint stiffness, and impaired function) indices, 100 and 200 mg bid had the same effects as 500 mg bid of naproxen. 200 mg qd and 100 mg bid had similar effects on OA symptoms.
For RA: 100 and 200 mg bid significantly relieved RA symptoms in clinical trials, equivalent to 500 mg bid of naproxen. 100, 200, and 400 mg bid had similar effects on the number of RA patients suffering from joint swelling and pain/tenderness, all equivalent to 500 mg bid of naproxen.

Side Effects

Occasional gastrointestinal reactions. Small effects on renal function and platelets. Acute overdose can cause fatigue, drowsiness, nausea, vomiting, and upper abdominal pain, which can be relieved with treatment. Gastrointestinal bleeding is possible. In rare cases, hypertension, acute renal failure, respiratory depression, and comas may occur.

Warnings and Precautions

Anyone who is allergic to any ingredient in Celecoxib or who is known to be allergic to sulfa drugs should not take it.
It should be avoided in patients with asthma, urticaria, or acute rhinitis.
Lactating women should not take it.
May slow down metabolism and increase serum concentration in combination with leukotriene antagonist zafirlukast, antifungal agent fluconazole, and lipid-lowering statin drug fluvastatin.
Celecoxib can increase blood concentration of beta blockers, antidepressants and antipsychotic drugs, so care should be taken when using these drugs.

Description

Celecoxib is a nonsteroidal antiinflammatory drug (NSAID) first launched as Celebrex in the US for the treatment of symptoms in patients with rheumatoid arthritis (RA) and osteoarthritis (OA). Celecoxib belongs to a new class of 1, 5-diarylpyrazoles and can be synthesized by heat-promoted heterocyclization of a trifiuoro-l,3-dione with appropriate arylhydrazine. Celecoxib is a highly selective inhibitor of COX-2, the inducible form of cyclooxygenase expressed during inflammatory processes; it does not block the constitutive form COX-1, thus suppressing the gastric and intestinal toxicity of most non-selective NSAIDs. The potency ratio COX1/COX2 on purified human enzymes was about 400. In several in vivo models of acute and chronic inflammation, Celecoxib demonstrated potent antiinflammatory activity without affecting gastric or urinary prostaglandin PGE2. In several clinical studies performed with patients suffering from osteoarthritis or rheumatoid arthritis, Celecoxib was shown to be well tolerated and to relieve pain and inflammation more efficiently compared with other standard NSAIDs; the gastrointestinal safety profile was significantly better than that of other NSAIDs. Interestingly, Celecoxib was approved for another indication in patients with familial adenomatous polyposis (FAP). A six-month clinical trial demonstrated a 28% reduction in the number of colorectal polyps with Celecoxib, compared to a 5% reduction with placebo.

Chemical Properties

White to Pale Yellow Solid

Originator

Searle (US)

Uses

expectorant, gastric stimulant, insecticide

Uses

For relief and management of osteoarthritis (OA), rheumatoid arthritis (RA), juvenile rheumatoid arthritis (JRA), ankylosing spondylitis, acute pain, primary dysmenorrhea and oral adjunct to usual care for patients with familial adenomatous polyposis

Uses

A selective cyclooxygenase-2 (COX-2) inhibitor. Anti-inflammatory. Used in treatment of familial adenomatous polyposis

Indications

Celecoxib is indicated for the treatment of osteoarthritis and rheumatoid arthritis. Its use is contraindicated in individuals with hypersensitivity to sulfonamides or other NSAIDs. It should be used with caution in persons with hepatic disease. Interactions occur with other drugs that induce CYP2C9 (e.g. rifampin rifampin) or compete for metabolism by this enzyme (e.g. fluconazole, leflunomide). The most common adverse reactions to celecoxib are mild to moderate GI effects such as dyspepsia, diarrhea, and abdominal pain. Serious GI and renal effects have occurred rarely.

brand name

Celebrex (Searle).

General Description

Celecoxib (Celebrex) was the first selective COX-2 inhibitordrug introduced into the market in 1998 for use in thetreatment of RA, OA, acute pain, and menstrual pain. Thereal benefit is that it has caused fewer GI complicationswhen compared with other conventional NSAIDs. It hasalso been approved for reducing the number of adenomatouscolorectal polyps in familial adenomatous polyposis (FAP).Celecoxib is well absorbed and undergoes rapid oxidativemetabolism via CYP2C9 to give its inactive metabolites. Thus, a potential drug interaction exists betweencelecoxib and warfarin because the active isomer ofwarfarin is primarily degraded by CYP2C9.

Biological Activity

Selective cyclooxygenase-2 (COX-2) inhibitor (IC 50 values are 15 and 0.04 μ M for COX-1 and COX-2 respectively). Anti-inflammatory with shorter plasma half-life in vivo than SC 58121 (5-(4-Fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole ). Displays chemopreventive activity in in vivo tumor models.

Celecoxib Preparation Products And Raw materials

Raw materials

Preparation Products


Celecoxib Suppliers

Global( 409)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19919 60
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3203 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21910 58
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1530 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 495 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1367 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2543 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 bruce@xrdchem.cn CHINA 541 55

View Lastest Price from Celecoxib manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-20 Celecoxib
169590-42-5
US $7.00 / KG 1KG 99% 100KG career henan chemical co
2018-08-14 CELECOXIB
169590-42-5
US $1.00 / KG 1KG 99% 20kg career henan chemical co
2018-07-26 Fenazox
169590-42-5
US $100.00 / KG 1KG 98% 100KG career henan chemical co

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