ChemicalBook > CAS DataBase List > Valdecoxib

Valdecoxib

Product Name
Valdecoxib
CAS No.
181695-72-7
Chemical Name
Valdecoxib
Synonyms
BEXTRA;Valz;Valus;CS-592;SC 65872;Valecoxib;VALDECOXIB;AKOS 92130;Vatdecoxib;BEXTRA;SC 65872
CBNumber
CB4754453
Molecular Formula
C16H14N2O3S
Formula Weight
314.36
MOL File
181695-72-7.mol
More
Less

Valdecoxib Property

Melting point:
162-164°C
Boiling point:
481.2±55.0 °C(Predicted)
Density 
1.303±0.06 g/cm3(Predicted)
storage temp. 
room temp
solubility 
DMSO: >25mg/mL
pka
9.83±0.10(Predicted)
form 
powder
color 
white to off-white
InChI
InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
InChIKey
LNPDTQAFDNKSHK-UHFFFAOYSA-N
SMILES
C1(S(N)(=O)=O)=CC=C(C2=C(C)ON=C2C2=CC=CC=C2)C=C1
CAS DataBase Reference
181695-72-7(CAS DataBase Reference)
More
Less

Safety

Hazard Codes 
Xn,N
Risk Statements 
63-48/22-51/53
Safety Statements 
36/37-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
Hazardous Substances Data
181695-72-7(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PZ0179
Product name
Valdecoxib
Purity
≥98% (HPLC)
Packaging
5mg
Price
$88.2
Updated
2024/03/01
Cayman Chemical
Product number
10006120
Product name
Valdecoxib
Purity
≥98%
Packaging
5mg
Price
$72
Updated
2024/03/01
Cayman Chemical
Product number
10006120
Product name
Valdecoxib
Purity
≥98%
Packaging
10mg
Price
$129
Updated
2024/03/01
Sigma-Aldrich
Product number
PZ0179
Product name
Valdecoxib
Purity
≥98% (HPLC)
Packaging
25mg
Price
$581
Updated
2024/03/01
Cayman Chemical
Product number
10006120
Product name
Valdecoxib
Purity
≥98%
Packaging
25mg
Price
$301
Updated
2024/03/01
More
Less

Valdecoxib Chemical Properties,Usage,Production

Description

Valdecoxib is a second-generation COX-2 inhibitor, developed as a follow-up to celecoxib for the oral once-daily treatment of osteoarthritis, adult rheumatoid arthritis and menstrual pain. Valdecoxib is approximately 28,000-fold more selective against human recombinant COX-2 than human recombinant COX-1. In an ex viva human whole blood assay, the I&O values against COX-2 and COX-1 were respectively 0.89 PM and 25.4 FM. In animal models, valdecoxib possesses excellent oral activity as an antiinflammatory. In rats, valdecoxib potently inhibited carrageenan footpad edema and adjuvant-induced arthritis.

Chemical Properties

Valdecoxib is a white crystalline powder that is relatively insoluble in water (10 μg/mL) at 25°C and pH 7.0, soluble in methanol and ethanol, and freely soluble in organic solvents and alkaline (pH=12) aqueous solutions.

Originator

Pharmacia (Searle) (USA)

Uses

Valdecoxib is a nonsteroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory, analgesic and antipyretic properties in animal models. It is a potent and selective inhibitor of prostaglandin synthesis primarily through inhibition of COX-2. Valdecoxib is used to relieve some symptoms caused by arthritis (rheumatism), such as inflammation, swelling, stiffness, and joint pain.

Definition

ChEBI: Valdecoxib is a member of the class of isoxazoles that is isoxazole which is substituted at positions 3, 4 and 5 by phenyl, p-sulfamoylphenyl and methyl groups, respectively. A selective cyclooxygenase 2-inhibitor, it used as a nonsteroidal anti-inflammatory drug (NSAID) for the treatment of arthritis from 2001 until 2005, when it was withdrawn following concerns of an associated increased risk of heart attack and stroke. It has a role as a non-steroidal anti-inflammatory drug, a cyclooxygenase 2 inhibitor, a non-narcotic analgesic, an antirheumatic drug and an antipyretic. It is a member of isoxazoles and a sulfonamide.

Preparation

The step for the synthesis of valdecoxib: Deoxybenzoin is converted to the corresponding oxime by treatment with hydroxylamine under basic conditions with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol. The treatment of the oxime under nitrogen with two equivalents of butyllithium in tetrahydrofuran is followed by cyclization in ethyl acetate or acetic anhydride to the isoxazoline derivative. Finally, treatment of the isoxazoline with cold chlorosulfuric acid followed by reaction of the intermediate with aqueous ammonia afforded valdecoxib.

brand name

Bextra (Searle).

General Description

Valdecoxib (VCX) is a diaryl substituted isoxazole compound. It comprises of sulfonyl propanamide and is a metabolite of parecoxib.

Biochem/physiol Actions

Valdecoxib is reported to elicit anti-inflammatory, analgesic and antipyretic functionality. It acts as a substrate for the liver enzyme cytochrome P450 2C9(CYP2C9) and cytochrome P450 3A4 (CYP3A4).

Pharmacokinetics

Valdecoxib is freely soluble in alkaline aqueous solutions. At recommended doses, the mean oral bioavailability for valdecoxib is 83%, and the time to peak concentration is approximately 3 hours. Time to peak plasma concentration was delayed by 1 to 2 hours when administered with a high-fat meal. Protein binding is very high at 98%. Valdecoxib exhibits linear pharmacokinetics over the usual clinical dose range. Valdecoxib is extensively metabolized in humans. The primary metabolite for valdecoxib involved CYP2C9 hydroxylation of the 5-Me group, which was further metabolized to the inactive carboxylate, and N-hydroxylation at the sulfonamide moiety. Oxidative breakdown of the N-hydroxy sulfonamide function group led to the formation of the corresponding sulfinic acid and sulfonic acid metabolites. The O-and N-glucuronides were the major urinary metabolites. Only 3% of the administered dose was recovered in urine as unchanged valdecoxib.

Clinical Use

Valdecoxib is approved for the relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis and for the treatment of primary dysmenorrhea. Valdecoxib is contraindicated for the treatment of postoperative pain immediately following coronary artery bypass graft surgery.

Synthesis

Deoxybenzoin is converted to the corresponding oxime by treatment with hydroxylamine under basic conditions with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol. The treatment of the oxime under nitrogen with two equivalents of butyllithium in tetrahydrofuran is followed by cyclization in ethyl acetate or acetic anhydride to the isoxazoline derivative. Finally, treatment of the isoxazoline with cold chlorosulfuric acid followed by reaction of the intermediate with aqueous ammonia affords the desired product .

storage

Store at RT

Clinical claims and research

Valdecoxib is a substrate of CYP3A4 but no metabolism interference was seen with commonly used synthetic narcotics, alfentanil and fentanyl. Clinical studies have shown that valdecoxib is as effective as naproxen in treating osteoarthritis, rheumatoid arthritis and dysmenornhoea. The efficacy of valdecoxib was also demonstrated in managing postoperative pain (oral and orthopedic surgery) with effective analgesia and time to rescue medication superior to those obtained with rofecoxib. Several clinical trials showed that valdecoxib has a better upper gastrointestinal safety profile compared to naproxen, ibuprofen or diclofenac and does not affect platelet function. Less abdominal pain, dyspepsia and constipation were observed with valdecoxib than with naproxen. Valdecoxib is contraindicated in patients with a history of allergic reactions to sulfonamides due to reported anaphylactic and skin reactions.

Mode of action

Valdecoxib is a nonsteroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory, analgesic and antipyretic properties in animal models. The mechanism of action is believed to be due to inhibition of prostaglandin synthesis primarily through inhibition of cyclooxygenase-2 (COX-2). At therapeutic plasma concentrations in humans valdecoxib does not inhibit cyclooxygenase-1 (COX-1).

References

[1] talley j j, brown d l, carter j s, et al. 4-[5-methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: a potent and selective inhibitor of cox-2. journal of medicinal chemistry, 2000, 43(5): 775-777.
[2] nussmeier n a, whelton a a, brown m t, et al. complications of the cox-2 inhibitors parecoxib and valdecoxib after cardiac surgery. new england journal of medicine, 2005, 352(11): 1081-1091.

Valdecoxib Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Valdecoxib Suppliers

Austria 1 Belgium 1 Brazil 1 Canada 1 China 282 Europe 2 Germany 3 India 25 Japan 1 Poland 1 South Korea 1 United Kingdom 12 United States 46 Global 377
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
Alfa Chemistry
Tel
1-516-6625404
Fax
1-516-927-0118
Email
support@alfa-chemistry.com
Country
United States
ProdList
9171
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Cckinase, Inc.
Tel
+1 (732)236-3202
Email
sales@cckinase.com
Country
United States
ProdList
2738
Advantage
58
Standardpharm Co. Ltd.
Tel
86-714-3992388
Email
overseasales1@yongstandards.com
Country
United States
ProdList
14332
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81215950 4000-868-328
Email
customer@uwalab.com
Country
United States
ProdList
10404
Advantage
58
TargetMol Chemicals Inc.
Tel
+8613564774135
Email
zijue.cai@tsbiochem.com
Country
United States
ProdList
19885
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
China.
Tel
--
Fax
--
Country
United States
ProdList
116
Advantage
50
BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
ProdList
9923
Advantage
65
Olinax Inc.
Tel
--
Fax
--
Email
info@olinax.com
Country
United States
ProdList
404
Advantage
50
Texas Biochemicals Inc.
Tel
--
Fax
--
Email
info@texasbiochemicals.com
Country
United States
ProdList
217
Advantage
50
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
JR MediChem LLC
Tel
--
Fax
--
Email
sales@jrmedichem.com
Country
United States
ProdList
86
Advantage
0
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Axon Medchem LLC
Tel
--
Fax
--
Email
info@axonmedchem.com
Country
United States
ProdList
763
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
W & J PharmaChem, Inc.
Tel
--
Fax
--
Email
info@wjpharmachem.com
Country
United States
ProdList
595
Advantage
50
OChem Incorporation
Tel
--
Fax
--
Email
sales@ocheminc.com
Country
United States
ProdList
6501
Advantage
60
Labseeker Inc
Tel
--
Fax
--
Email
marketing@labseeker.com
Country
United States
ProdList
1495
Advantage
55
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
Selleck Chemicals LLC
Tel
--
Fax
--
Email
info@selleckchem.com
Country
United States
ProdList
824
Advantage
60
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
Medical Isotopes
Tel
--
Fax
--
Email
stohler@medicalisotopes.com
Country
United States
ProdList
6181
Advantage
68
Ryan Scientific, Inc.
Tel
--
Fax
--
Email
ryan.reichlyn@ryansci.com
Country
United States
ProdList
6439
Advantage
60
SLN Pharmachem
Tel
--
Fax
--
Email
slnpharmachem@vsnl.net
Country
United States
ProdList
188
Advantage
43
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
SynFine Research
Tel
--
Fax
--
Email
research@synfine.com
Country
United States
ProdList
1024
Advantage
68
ChemPacific Corporation
Tel
--
Fax
--
Email
sales@chempacific.com
Country
United States
ProdList
6891
Advantage
51
XENOS Bioresources, Inc.
Tel
--
Fax
--
Email
xenos@west.net
Country
United States
ProdList
122
Advantage
38
American Custom Chemicals Corporation
Tel
--
Fax
--
Email
sales@acccorporation.com
Country
United States
ProdList
6820
Advantage
51
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
More
Less

View Lastest Price from Valdecoxib manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Valdecoxib 181695-72-7
Price
US $0.00-0.00/g
Min. Order
100g
Purity
99%min
Supply Ability
100kg
Release date
2022-11-16
Hebei Weibang Biotechnology Co., Ltd
Product
Valdecoxib 181695-72-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-21
Hebei Ganmiao New material Technology Co., LTD
Product
Valdecoxib 181695-72-7
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
20ton
Release date
2024-06-06

181695-72-7, ValdecoxibRelated Search:

Parecoxib Valerophenone Parecoxib Impurity 21 Parecoxib Impurity 12 N-((4-(5-Methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)acetaMide Tamoxifen Acyclovir 3-methyl -4,5-diphenyl-4,5-didydro-isoxazole 4-(4-chlorophenyl)-5-methyl-3-phenylisoxazole Rofecoxib Etoricoxib Valdecoxib Deoxy Benzoin ( Benzyl Phenyl Ketone Or VALDECOXIB-D3 Parecoxib Impurity 6 Valdecoxib Valdecoxib-13C2, 15N PARECOXIB NA 4-[(5-DIFLUOROMETHYL-3-PHENYL)-4-ISOXAZOLYL]BENZENESULFONAMIDE

  • BEXTRA
  • VALDECOXIB
  • 4-(5-METHYL-3-PHENYL-4-ISOXAZOLYL)BENZENESULFONAMIDE
  • AKOS 92130
  • BEXTRA(VALDECOXIB)
  • Parecoxib Sodium-7
  • Valdecoxib - SC 65872 | Bextra
  • Parecoxib sodium intermediate
  • BEXTRA;SC 65872
  • Parecoxib Impurity 7（Valdecoxib）
  • CS-592
  • Parecoxib Impurity E: Vardecoxib
  • Bextra, 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenefulfonamide
  • 4-(5-methyl-3-phenyl-oxazol-4-yl)benzenesulfonamide
  • Bextra, 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide
  • 4-(5-methyl-3-phenyl-isoxazol-4-yl)benzenesulfonamide
  • SC 65872
  • Valecoxib
  • Valus
  • Valz
  • 4-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide
  • Parecoxib SodiuM interMediate B
  • Benzenesulfonamide, 4-(5-methyl-3-phenyl-4-isoxazolyl)-
  • Valdecoxib Solution, 100ppm
  • Valdecoxib (This product is only available in Japan.)
  • Parecoxib Impurity 4
  • 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfomide
  • Valdecoxib Parecoxib Sodium intermediates
  • Valdecoxib, 98%, a COX-2 selective inhibitor
  • 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide
  • Vatdecoxib
  • 4-(5-Methyl-3-phenyl-4-isooxazolyl)benzenesulfonamide
  • VALDECOXIB ISO 9001：2015 REACH
  • 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenefulfonamide
  • parecoxib sulfonamide
  • Valdecoxib (SC65872)
  • TIANFU-CHEM Benzenesulfonamide,4-(5-methyl-3-phenyl-4-isoxazolyl)-
  • PARECOXIB SULFOMIDE
  • Valdecoxib（Parecoxib Sodium Impurity 8）
  • Parecoxib Impurity 7 CRS
  • 181695-72-7
  • 181695-72-1
  • C1614N2O3S
  • SC-65872, YM-974
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Amines
  • Aromatics
  • Heterocycles
  • Sulfur & Selenium Compounds
  • Active Pharmaceutical Ingredients
  • Osteoarthritis and Rheumatoid Arthritis