Related Searches: Celecoxib

Celecoxib(CAS No. 169590-42-5)

Celecoxib C17H14F3N3O2S (cas 169590-42-5) Molecular Structure

169590-42-5 Structure

Identification and Related Records

【Name】
Celecoxib
【CAS Registry number】
169590-42-5
【Synonyms】
Celebrex (TN)
SC 58635
YM177
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
YM 177
Celecoxib (JAN/USAN)
benzenesulfonamide, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
【Molecular Formula】
C17H14F3N3O2S (Products with the same molecular formula)
【Molecular Weight】
381.37217
【Inchi】
InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
【InChIKey】
RZEKVGVHFLEQIL-UHFFFAOYSA-N
【Canonical SMILES】
CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
【MOL File】
169590-42-5.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
1.43 g/cm3
【Melting Point】
157-159℃
【Vapour】
2.81E-11mmHg at 25°C
【Flash Point】
273.7 °C
【Water】
Insoluble
【Solubilities】
Insoluble Appearance:white powder
Transport Information:UN 2811
Hazard Symbols:UN NO.
Deleted CAS:184007-95-2
【Color/Form】
Pale yellow solid
【Computed Properties】
Molecular Weight:381.37217 [g/mol]
Molecular Formula:C17H14F3N3O2S
XLogP3-AA:3.4
H-Bond Donor:1
H-Bond Acceptor:7
Rotatable Bond Count:3
Exact Mass:381.075882
MonoIsotopic Mass:381.075882
Topological Polar Surface Area:86.4
Heavy Atom Count:26
Formal Charge:0
Complexity:577
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:1
Feature 3D Ring Count:3
Effective Rotor Count:4
Conformer Sampling RMSD:0.8
CID Conformer Count:4

Safety and Handling

【Hazard Codes】
UN NO.
【Risk Statements】
R20/21/22
【Safety Statements 】
S22;S24/25;S28;S37/39
【Safety】

Hazard Codes of Celecoxib (CAS NO.169590-42-5):?HarmfulXn
Risk Statements: 20/21/22?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-24/25-28-37/39?
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.?
S28: After contact with skin, wash immediately with plenty of soap-suds.?
S37/39: Wear suitable gloves and eye/face protection.

【Transport】
UN 2811
【Formulations/Preparations】
Celecoxib is the active ingredient in the drug Celebrex produced by GD Searle LLC (oral capsules)
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl celecoxib, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Octanol/Water Partition Coefficient】
log Kow = 3.47 /Estimated/
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: J. J. Talley et al., WO 95 15316; eidem, US 5466823 (both 1995 to Searle)

Biomedical Effects and Toxicity

【Pharmacological Action】
- A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2.
【Therapeutic Uses】
Celecoxib is indicated to relieve the signs and symptoms of rheumatoid arthritis and osteoarthritis. /Included in US product labeling/
Celecoxib is indicated for the relief of the pain of primary dysmenorrhea. /Included in US product labeling/
Celecoxib is indicated to reduce the number of adenomatous colorectal polyps in patients with familial adenomatous polyps, as an adjunct to usual care. /Included in US product labeling/
Celecoxib is indicated for the relief of acute pain rated as moderate to severe, such as following dental or orthopedic surgery. /Included in US product labeling/
【Biomedical Effects and Toxicity】
Peak plasma levels of celecoxib occur approximately 3 hrs after an oral dose. Under fasting conditions, both peak plasma levels (Cmax ) and area under the curve (AUC) are roughly dose proportional up to 200 mg /twice daily/; at higher doses there are less than proportional increases in Cmax and AUC. Absolute bioavailability studies have not been conducted. With multiple dosing, steady state conditions are reached on or before day 5.
Administration of celecoxib with a high-fat meal resulted in a 1 to 2 hour delay in the peak plasma concentration level and a 10 to 20% increase in the area under the plasma concentration-time curve (AUC). Celecoxib may be coadministered with meals without altering the dosing schedule based on the timing of meals.
In healthy subjects, celecoxib is highly protein bound (approx 97%) within the clinical dose range. In vitro studies indicate that celecoxib binds primarily to albumin and, to a lesser extent, (alpha) 1 -acid glycoprotein. The apparent volume of distribution at steady state (V ss /F) is approximately 400 L, suggesting extensive distribution into the tissues. Celecoxib is not preferentially bound to red blood cells.
Celecoxib is eliminated predominantly by hepatic metabolism with little (
Celecoxib is distributed in the milk of lactating rats at concentrations similar to those in plasma. It is not known whether the drug is distributed in human milk.
A pharmacokinetic study in subjects with mild (Child-Pugh Class A) and moderate (Child-Pugh Class B) hepatic impairment has shown that steady-state celecoxib AUC is increased about 40% and 180%, respectively, above that seen in healthy control subjects.
In a cross-study comparison, celecoxib AUC was approximately 40% lower in patients with chronic renal insufficiency (GFR 35-60 mL/min) than that seen in subjects with normal renal function.
At steady state, elderly subjects (over 65 years old) had a 40% higher Cmax and a 50% higher AUC compared to the young subjects. In elderly females, celecoxib Cmax and AUC are higher than those for elderly males, but these increases are predominantly due to lower body weight in elderly females.
Meta-analysis of pharmacokinetic studies has suggested an approximately 40% higher AUC of celecoxib in Blacks compared to Caucasians.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150,000(SRC), determined from a structure estimation method(2), indicates that celecoxib is expected to be immobile in soil(SRC). Volatilization of celecoxib from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole(SRC), estimated using a fragment constant estimation method(3). Celecoxib is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150,000(SRC), determined from a structure estimation method(2), indicates that celecoxib is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 94(SRC), from an estimated log Kow of 3.47(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), celecoxib, which has an estimated vapor pressure of 1.2X10-9 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase celecoxib may be removed from the air by wet and dry deposition(SRC).

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