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Parecoxib

Parecoxib structure

CAS No:
198470-84-7
Formula:
C19H18N2O4S
Chemical Name:
Parecoxib
Synonyms:
Propanamide,N-[[4-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl]-;N-[[4-(5-Methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl]propanamide;Parecoxib;SC 69124;Vorth-P;Valus-P;Xapit
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

ChEBI: An N-acylsulfonamide resulting from the formal condensation of valdecoxib with propionic acid. It is a prodrug for valdecoxib.

Parecoxib is an N-acylsulfonamide resulting from the formal condensation of valdecoxib with propionic acid. It is a prodrug for valdecoxib. It has a role as a cyclooxygenase 2 inhibitor, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug and a prodrug. It is a member of isoxazoles and a N-sulfonylcarboxamide. It derives from a valdecoxib.|Parecoxib is a water-soluble and injectable prodrug of valdecoxib. It is marketed as Dynastat in the European Union. Parecoxib is a COX2 selective inhibitor in the same category as celecoxib (Celebrex) and rofecoxib (Vioxx). As it is injectable, it can be used perioperatively when patients are unable to take oral medications. It is approved through much of Europe for short term perioperative pain control much in the same way ketorolac (Toradol) is used in the United States. A letter of non-approval for parecoxib was issued by the FDA in 2005.|Parecoxib is an amide prodrug of the cyclooxygenase II (COX-2) selective, non-steroidal anti-inflammatory drug (NSAID) valdecoxib, with anti-inflammatory, analgesic, and antipyretic activities. Upon administration, parecoxib is hydrolyzed by hepatic carboxyesterases to its active form, valdecoxib. Valdecoxib selectively binds to and inhibits COX-2. This prevents the conversion of arachidonic acid into prostaglandins, which are involved in the regulation of pain, inflammation, and fever. This NSAID does not inhibit COX-1 at therapeutic concentrations and, therefore, does not interfere with blood coagulation.

Parecoxib Basic Attributes

Molecular Weight：

370.423

Exact Mass：

370.42

EC Number：

1308068-626-2

UNII：

9TUW81Y3CE

DSSTox ID：

DTXSID1044229

NCI Thesaurus Code：

C66318

ATC Code：

M01AH04|M - Musculo-skeletal system

Characteristics

PSA：

97.6

XLogP3：

3.3

Density：

1.264

Melting Point：

148.9-151°

Refractive Index：

1.580

Collision Cross Section：

189.2 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

63-48/22-51/53

safety instructions：

36/37-61

RTECS Number：

TX1478700

Marks：

Xn,N

Precautionary statement(s)：

P281

Hazard Statements：

H361d-H373

GHS Classification：

|Warning|H361 (95%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P260, P281, P308+P313, P314, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Protein Binding：

98%

Drug Information

Drug Indication：

Used for short term perioperative pain control.|For the short-term treatment of postoperative pain in adults.,|For the short-term treatment of postoperative pain.The decision to prescribe a selective COX-2 inhibitor should be based on an assessment of theindividual patient's overall risks (see sections 4.3, 4.4).|For the short-term treatment of postoperative pain.

MeSH：

A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. (See all compounds classified as Cyclooxygenase 2 Inhibitors.)

Metabolism/Metabolites：

Hepatic. Metabolized primarily via CYP3A4 and 2C9 to valdecoxib and propionic acid.

Biological Half-Life：

22 minutes (parecoxib); 8 hours (valdecoxib)

MeSH Entry Terms：

Dynastat

Parecoxib Use and Manufacturing

Methods of Manufacturing

3.1 g (10 mmol) of valdecoxib was mixed with 3.5 g (35 mmol) of triethylamine and 2.6 g (20 mmol) of propionic anhydride at 20 ° CDichloromethane, after the reaction, pour into water, dichloromethane extraction, concentration, ethanol dissolved, 5 ~ 10 crystallization, Filtering and drying to obtain 3.4g of parecoxib, the yield is 92.5percent and the purity is 99.77percentThe valdecoxib 3.1g (10mmol) and triethylamine 3.5g (35mmol) and propionic anhydride 2.6g (20mmol) were mixed in 20 Methylene chloride, after completion of the reaction, poured into water and extracted with methylene chloride, concentrated, dissolved in ethanol, 5 ~ 10 crystallization, Filtration, drying parecoxib 3.4g, yield 92.7percent, purity of 99.61percent.3.1 g (10 mmol) of valdecoxib was mixed with 3 g (30 mmol) of triethylamine, And propionic anhydride (3.3 g, 25 mmol) were mixed in dichloromethane at 20 ° C, After completion of the reaction, Dumped into the water, Dichloromethane extraction, concentrate, Ethanol dissolved, 5 ~ 10 crystallization, filter, Drying was 3.4g of parecoxib, The yield was 92.4percentPurity 99.81percent.The raw material valdecoxib III (5.0g) was added to propionic anhydride (18.6g), and stirred to dissolve.Benzene sulfonic acid (0.25g) was added, and the temperature was raised to 50 to 60 ° C and reacted for about 3 hours.TLC monitoring reaction was complete, cooled to about 0 , incubated for about 1 hour.Filter, the filter cake with methyl tert-butyl ether (10ml) was rinsed in a vacuum oven, -0.08MPa ~ -0.1MPa, vacuum dried at 50 8 to 12 hours to obtain 4.90g parecoxib sodium intermediate I, yield 83.2percent.HPLC purity of 99.93percent, the largest single miscellaneous 0.05percent, the raw material valdecoxib III

Uses

Anti-inflammatory; analgesic (cyclooxygenase COX-2 inhibitor).

Use Classification：

Human drugs -> Dynastat -> EMA Drug Category|Coxibs, Antiinflammatory and antirheumatic products -> Human pharmacotherapeutic group|Human drugs -> Rayzon -> EMA Drug Category|Antiinflammatory and antirheumatic products -> Human pharmacotherapeutic group|Human drugs -> Xapit -> EMA Drug Category

Computed Properties

Molecular Weight:370.4
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:370.09872823
Monoisotopic Mass:370.09872823
Topological Polar Surface Area:97.6
Heavy Atom Count:26
Complexity:575
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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