Valdecoxib

Valdecoxib Properties

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
Henry's Law Constant	4.5×10⁵ mol/(m³Pa) at 25℃, HSDB (2015)
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)
EWG's Food Scores	1
NCI Dictionary of Cancer Terms	valdecoxib
FDA UNII	2919279Q3W
NCI Drug Dictionary	Bextra
ATC code	M01AH03
UNSPSC Code	12352200
NACRES	NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS08,GHS09
Signal word	Warning
Hazard statements	H361d-H373-H410
Precautionary statements	P201-P202-P260-P273-P280-P308+P313
Hazard Codes	Xn,N
Risk Statements	63-48/22-51/53
Safety Statements	36/37-61
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Chronic 1 Repr. 2 STOT RE 2
Hazardous Substances Data	181695-72-7(Hazardous Substances Data)

Valdecoxib price More Price(61)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	PZ0179	Valdecoxib ≥98% (HPLC)	181695-72-7	5mg	$162	2026-04-30	Buy
Cayman Chemical	10006120	Valdecoxib ≥98%	181695-72-7	5mg	$80	2026-04-30	Buy
Cayman Chemical	10006120	Valdecoxib ≥98%	181695-72-7	10mg	$142	2026-04-30	Buy
Cayman Chemical	10006120	Valdecoxib ≥98%	181695-72-7	25mg	$332	2026-04-30	Buy
Cayman Chemical	10006120	Valdecoxib ≥98%	181695-72-7	50mg	$622	2026-04-30	Buy

Product number	Packaging	Price	Buy
PZ0179	5mg	$162	Buy
10006120	5mg	$80	Buy
10006120	10mg	$142	Buy
10006120	25mg	$332	Buy
10006120	50mg	$622	Buy

Valdecoxib Chemical Properties, Uses, 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.
synthesis of 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 .
Synthesis_181695-72-7

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 synthesis

Synthesis of Valdecoxib from 5-Methyl-3,4-diphenylisoxazole

Valdecoxib Preparation Products And Raw materials

Raw materials

Diphenhydramine Hydroxylamine Sodium acetate 5-Methyl-3,4-diphenylisoxazole 5-Methyl-3,4-diphenyl-4,5-dihydroisoxazol-5-ol

Preparation Products

Parecoxib N-((4-(5-Methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)acetaMide Valdecoxib IMpurity B 1-Hydroxy Valdecoxib

Valdecoxib Suppliers

Global Suppliers ( 417)

Supplier	Tel	Email	Country	ProdList	Advantage
Shandong Chuangye Pharmaceutical Technology Co., Ltd.	13325129676	3610186177@qq.com	China	22	58
Hangzhou Benoy Chemical Co., Ltd.	17342059697	sales@benoychem.com	China	209	58
Shandong Mingfeng Pharmaceutical and Technology Co. Ltd	053155551677 15315114555	1345456643@qq.com	China	298	58
TIANJIN PHARMACN MEDICAL TECHNOLOGY CO.,LTD.	022-60189726 18812034280	188120342808@163.com	China	143	61
Shanghai Boyle Chemical Co., Ltd.		sales@boylechem.com	China	2915	55
J & K SCIENTIFIC LTD.	18210857532 18210857532	jkinfo@jkchemical.com	China	96815	76
3B Pharmachem (Wuhan) International Co.,Ltd.	18930552037	3bsc@sina.com	China	15813	69
Chembest Research Laboratories Limited	021-20908456	sales@BioChemBest.com	China	5996	61
Energy Chemical	400-0056266	sales8178@energy-chemical.com	China	44850	61
Jia Xing Isenchem Co.,Ltd	0573-85285100 18627885956	isenchem@163.com	China	9389	66

Supplier	Advantage
Shandong Chuangye Pharmaceutical Technology Co., Ltd.	58
Hangzhou Benoy Chemical Co., Ltd.	58
Shandong Mingfeng Pharmaceutical and Technology Co. Ltd	58
TIANJIN PHARMACN MEDICAL TECHNOLOGY CO.,LTD.	61
Shanghai Boyle Chemical Co., Ltd.	55
J & K SCIENTIFIC LTD.	76
3B Pharmachem (Wuhan) International Co.,Ltd.	69
Chembest Research Laboratories Limited	61
Energy Chemical	61
Jia Xing Isenchem Co.,Ltd	66

View Latest Price from Valdecoxib manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2026-09-16	Valdecoxib 181695-72-7		100g	99%min	100kg	WUHAN FORTUNA CHEMICAL CO., LTD
2026-08-20	VALDECOXIB 181695-72-7	$1.10	1g	99.0% Min	100 Tons	Dideu Industries Group Limited
2026-07-27	Valdecoxib 181695-72-7	$59.00-196.00		99.89%	10g	TargetMol Chemicals Inc.

Valdecoxib
181695-72-7
99%min
WUHAN FORTUNA CHEMICAL CO., LTD

VALDECOXIB
181695-72-7
$1.10
99.0% Min
Dideu Industries Group Limited

Valdecoxib
181695-72-7
$59.00-196.00
99.89%
TargetMol Chemicals Inc.

Valdecoxib Spectrum

Valdecoxib(181695-72-7)¹HNMR

181695-72-7 (Valdecoxib) Related Search:

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Valdecoxib-13C2, 15N PARECOXIB NA 4-[(5-Difluoromethyl-3-phenyl)-4-isoxazolyl]benzenesulfonamide

1of4

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)- Valdecoxib（Parecoxib Sodium Impurity 8） PARECOXIB SULFOMIDE Parecoxib Impurity 7 CRS Valdecoxib, 10 mM in DMSO Valdecoxib 98% Valdecoxib Precursor Valdecoxib Sodium Precursor 4-(5-methyl-3-phenyl-4-isoazoleyl)benzenesulfonylamide 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide (Valdecoxib) 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