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Details

Stereochemistry ACHIRAL
Molecular Formula C19H18N2O4S
Molecular Weight 370.424
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARECOXIB

SMILES

CCC(=NS(=O)(=O)c1ccc(cc1)-c2c(C)onc2-c3ccccc3)O

InChI

InChIKey=TZRHLKRLEZJVIJ-UHFFFAOYSA-N
InChI=1S/C19H18N2O4S/c1-3-17(22)21-26(23,24)16-11-9-14(10-12-16)18-13(2)25-20-19(18)15-7-5-4-6-8-15/h4-12H,3H2,1-2H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula C19H18N2O4S
Molecular Weight 370.424
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including https://www.medicines.org.uk/emc/medicine/8771

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. In 2005, the U.S. Food and Drug Administration (FDA) issued a letter of non-approval for parecoxib in the United States. Parecoxib is indicated for the short-term treatment of postoperative pain in adults.

Originator

Curator's Comment:: # Pfizer

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Dynastat

Approved Use

Dynastat is used for the short-term treatment of pain in adults after an operation.

Launch Date

1016668800000
PubMed

PubMed

TitleDatePubMed
[Clinical pharmacology of the selective COX-2 inhibitors].
2003 Dec
The role of cyclooxygenase selective inhibitors in the gastrointestinal tract.
2003 Dec
Efficacy and safety of the first parenteral selective COX-2 inhibitor, parecoxib sodium, in adult patients with postoperative pain.
2003 Jul
Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population.
2003 Jul-Aug
Stability of reconstituted parecoxib for injection with commonly used diluents.
2003 Oct
Effect of selective inhibition of cyclooxygenase-2 on lipopolysaccharide-induced hyperalgesia.
2004
Clinical pharmacology of novel selective COX-2 inhibitors.
2004
[Pharmacology and classification of cyclooxygenase inhibitors].
2004 Apr
[Valdecoxib (Bextra)].
2004 Apr
Pharmacological profile of parecoxib: a novel, potent injectable selective cyclooxygenase-2 inhibitor.
2004 Apr 26
The second generation of COX-2 inhibitors: clinical pharmacological point of view.
2004 Aug
[Review of analgesics].
2004 Dec
Reaction between parecoxib and vecuronium.
2004 Dec
Reporting of clinical trials of analgesia.
2004 Feb
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor.
2004 Feb
Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations.
2004 Jul
Parecoxib: new preparation. A NSAID for postoperative pain: no proven advantage.
2004 Jun
Preoperative parenteral parecoxib and follow-up oral valdecoxib reduce length of stay and improve quality of patient recovery after laparoscopic cholecystectomy surgery.
2004 Jun
Early analgesic effects of parecoxib versus ketorolac following laparoscopic sterilization: a randomized controlled trial.
2004 Jun
Parecoxib: a shift in pain management?
2004 Mar
Role of parecoxib in pre-emptive analgesia: comparison of the efficacy and safety of pre- and postoperative parecoxib in patients undergoing general surgery.
2004 May
Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters.
2004 May
A systematic review of COX-2 inhibitors compared with traditional NSAIDs, or different COX-2 inhibitors for post-operative pain.
2004 May
Differential inhibition of fracture healing by non-selective and cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs.
2004 May
Parecoxib for parenteral analgesia in postsurgical patients.
2004 May
Analgesic efficacy of preoperative parecoxib sodium in an orthopedic pain model.
2004 May-Jun
The analgesic efficacy of intramuscular parecoxib sodium in postoperative dental pain.
2004 Nov
A clinical trial demonstrates the analgesic activity of intravenous parecoxib sodium compared with ketorolac or morphine after gynecologic surgery with laparotomy.
2004 Oct
Presurgical intravenous parecoxib sodium and follow-up oral valdecoxib for pain management after laparoscopic cholecystectomy surgery reduces opioid requirements and opioid-related adverse effects.
2004 Oct
Patients' global evaluation of analgesia and safety of injected parecoxib for postoperative pain: a quantitative systematic review.
2004 Sep
[Use of low molecular weight heparin (Clexane) together with selective COX-2 inhibitor (Dynastat--once or twice per day)].
2005
Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance.
2005
Parecoxib: renal failure.
2005 Apr
COX-2 inhibition prevents downregulation of key renal water and sodium transport proteins in response to bilateral ureteral obstruction.
2005 Aug
Cyclooxygenase-2 plays a central role in the genesis of pancreatitis and associated lung injury.
2005 Feb
Severe bronchospasm after parenteral parecoxib: cyclooxygenase-2 inhibitors: not the answer yet.
2005 Feb
The cyclooxygenase-2-specific inhibitor parecoxib sodium is as effective as 12 mg of morphine administered intramuscularly for treating pain after gynecologic laparotomy surgery.
2005 Feb
Role of cyclooxygenase-2 in lipopolysaccharide-induced hyperalgesia in formalin test.
2005 Jan
Selective cyclooxygenase-2 inhibition reverses microcirculatory and inflammatory sequelae of closed soft-tissue trauma in an animal model.
2005 Jan
Cyclooxygenase-2 is a target of KRASD12, which facilitates the outgrowth of murine C26 colorectal liver metastases.
2005 Jan 1
The meaning of pain relief in a clinical trial.
2005 Jun
Parecoxib versus ibuprofen.
2005 Mar
COX-2 inhibitors--lessons in drug safety.
2005 Mar 17
A randomized, double-blind comparison between parecoxib sodium and propacetamol for parenteral postoperative analgesia after inguinal hernia repair in adult patients.
2005 May
Changing role of COX-2 inhibitors in the perioperative period: is parecoxib really the answer?
2005 May
The cardioprotective effects of preconditioning with endotoxin, but not ischemia, are abolished by a peroxisome proliferator-activated receptor-gamma antagonist.
2005 May
Increased risk of cardiovascular events with parecoxib/valdecoxib: a systematic review and meta-analysis.
2005 Nov 25
COX-2 inhibitors and pain after oral surgery - pertinent papers 2002-2003.
2006 Apr
Single dose parecoxib significantly improves ventilatory function in early extubation coronary artery bypass surgery: a prospective randomized double blind placebo controlled trial.
2006 Feb
Combination therapy using the cyclooxygenase-2 inhibitor Parecoxib and radioimmunotherapy in nude mice with small peritoneal metastases of colonic origin.
2006 Jan
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: intravenously (IV) or intramuscularly (IM)
The recommended dose is 40 mg administered intravenously (IV) or intramuscularly (IM), followed every 6 to 12 hours by 20 mg or 40 mg as required, not to exceed 80 mg/day.
Route of Administration: Parenteral
100 uM parecoxib inhibited rat osteoclast differentiation by 94%
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:42:59 UTC 2021
Edited
by admin
on Sat Jun 26 02:42:59 UTC 2021
Record UNII
9TUW81Y3CE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARECOXIB
EMA EPAR   INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
PROPANAMIDE, N-((4-(5-METHYL-3-PHENYL-4-ISOXAZOLYL)PHENYL)SULFONYL)-
Systematic Name English
SC-69124
Code English
PARECOXIB [WHO-DD]
Common Name English
N-((P-(5-METHYL-3-PHENYL-4-ISOXAZOLYL)PHENYL)SULFONYL)PROPIONAMIDE
Common Name English
PARECOXIB [USAN]
Common Name English
PARECOXIB [INN]
Common Name English
PARECOXIB [EMA EPAR]
Common Name English
RAYZON
Brand Name English
PARECOXIB [MI]
Common Name English
XAPIT
Brand Name English
Classification Tree Code System Code
WHO-ATC M01AH04
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
EMA ASSESSMENT REPORTS RAYZON (WITHDRAWN: PAIN, POSTOPERATIVE)
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
EMA ASSESSMENT REPORTS XAPIT (WITHDRAWN: PAIN, POSTOPERATIVE)
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
WHO-VATC QM01AH04
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
NCI_THESAURUS C1323
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
Code System Code Type Description
PUBCHEM
119828
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
MERCK INDEX
M8410
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY Merck Index
RXCUI
279950
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY RxNorm
EPA CompTox
198470-84-7
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL1206690
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
FDA UNII
9TUW81Y3CE
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
INN
7816
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
MESH
C409945
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
EVMPD
SUB03650MIG
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
DRUG BANK
DB08439
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
IUPHAR
2895
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
NCI_THESAURUS
C66318
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
CAS
198470-84-7
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
WIKIPEDIA
PARECOXIB
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
DRUG CENTRAL
2063
Created by admin on Sat Jun 26 02:42:59 UTC 2021 , Edited by admin on Sat Jun 26 02:42:59 UTC 2021
PRIMARY
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