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Drug

D0019 | Celecoxib

Molecular Formula C17H14F3N3O2S
Molecular Weight 381.4
Structure
State solid
Clearance Apparent clearance (CL/F), single oral 200 mg dose, healthy subjects = 27.7 L/hr [FDA label].
Volume of distribution The apparent volume of distribution at steady state (Vss/F) is about 400 L, suggesting extensive distribution into various tissues. Celecoxib is not preferentially bound to red blood cells [FDA label].
Route of elimination Celecoxib is eliminated predominantly by hepatic metabolism with little (<3%) unchanged drug recovered in the urine and feces. 57% of the oral dose is excreted in the feces and 27% is excreted into the urine. The primary metabolite in urine and feces was the carboxylic acid metabolite (73%). The amount of glucuronide in the urine is low [FDA label].
Protein binding 97%, primarily to albumin in healthy patients [FDA label].
Half life The effective half-life is approximately 11 hours when a single 200 mg dose is given to healthy subjects. Terminal half-life is generally variable because of the low solubility of the drug thus prolonging absorption [FDA label].
Absorption Easily absorbed in the gastrointestinal tract. When a single dose of 200 mg is given to healthy subjects, peak plasma levels occur 3 hours after an oral dose. The peak plasma level is 705 ng/mL. Absolute bioavailability studies have not been conducted. When multiple doses are given, steady-state is reached on or before Day 5. When taken with a high-fat meal, peak plasma levels are delayed for about 1 to 2 hours with an increase in total absorption (AUC) of 10% to 20% [FDA label]. A meta-analysis of pharmacokinetic studies has suggested an approximately 40% higher AUC (area under the curve) of celecoxib in black patients compared to Caucasians for unknown reasons [L3296].
Description nonsteroidal anti-inflammatory drug (NSAID);selective cyclooxygenase-2 (COX-2) inhibitor

G

L

M

M01AH01 Celecoxib


[M01AH] Coxibs


[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS


[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS


[M] Musculoskeletal system

L01XX33 Celecoxib


[L01XX] Other antineoplastic agents


[L01X] OTHER ANTINEOPLASTIC AGENTS


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents

G01AE10 Combinations of sulfonamides


[G01AE] Sulfonamides


[G01A] ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS


[G01] GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS


[G] Genitourinary system and reproductive hormones

Toxicity Dose Time Species Model Method Action Positive criterion Reference
ELONGATION mouse neuron Mitochondrial morphology and neurite area measurements induce 269

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 277 companies from 13 notifications to the ECHA C&L Inventory.


H360 (92.06%): May damage fertility or the unborn child [Danger Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P281, P308+P313, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H360: May damage fertility or the unborn child [Danger Reproductive toxicity]


H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]


H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


 P201, P202, P273, P281, P308+P313, P391, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Adenomatous polyposis coli

  • Ankylosing spondylitis

  • Colon adenoma

  • Hypertension

  • Inflammation

  • Injury

  • Intestinal polyp

  • Juvenile idiopathic arthritis

  • Large intestine polyp

  • Ligament sprain

  • Osteoarthritis

  • Polyp

  • Rheumatoid arthritis

  • Soft tissue injury

  • Spondylitis

  • Spondyloarthropathy

  • Eye disorder (0.05)

  • Abdominal pain

  • Abdominal pain upper

  • Angina pectoris

  • Angina unstable

  • Arthralgia

  • Back pain

  • Body temperature increased

  • Bone disorder

  • Cardiac failure

  • Cerebrovascular accident

  • Cerebrovascular disorder

  • Cough

  • Deep vein thrombosis

  • Dermatitis

  • Diarrhoea

  • Dizziness

  • Dyspepsia

  • Dyspnoea

  • Flatulence

  • Gastrointestinal disorder

  • Gastrointestinal pain

  • Gastrooesophageal reflux disease

  • Headache

  • Hypertension

  • Infection

  • Infestation

  • Insomnia

  • Mediastinal disorder

  • Musculoskeletal discomfort

  • Nasopharyngitis

  • Nausea

  • Nervous system disorder

  • Oedema peripheral

  • Pharyngitis

  • Rash

  • Rhinitis

  • Sinusitis

  • Upper respiratory tract infection

  • Vertigo

  • Vomiting

    • 169590-42-5 184007-95-2 194044-54-7
    1oq5 4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide 4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide
    4-[5-(4-METHYLPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]BENZENESULFONAMIDE 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-pyrazol-1-yl]benzenesulfonamide 4-[5-(4-Methylphenyl)-3-trifluoromethyl)-1H-pyrazol-yl]benzenesulfonamide
    4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyazol-1-yl]benezenesulfonamide 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
    4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazol-1-yl] benzenesulfonamide 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide 4-[5-(p-tolyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
    5-(4-Methylphenyl)-1-(4-sulfamoylphenyl)-3-(trifluoromethyl)pyrazole 590C425 A25046
    AB00052396-07 AB00052396-08 AB00052396-09
    AB00052396_10 AB00052396_11 AB0012055
    ABP000291 AC-4228 ACT02648
    AI-525 AK-60967 AKOS015842517
    AM84588 AT-3762 BBL029086
    BCP02156 BCP9000507 BCPP000290
    BDBM11639 BIDD:GT0408 BP-30217
    BRD-K02637541-001-02-4 BRD-K02637541-001-06-5 BSPBio_003596
    Benzenesulfonamide, 4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)- Benzenesulfonamide,4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl) Benzenesulfonamide,4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
    C-6317 C07589 C17H14F3N3O2S
    CAS-169590-42-5 CCG-39354 CCRIS 9330
    CELEBCOXIB CEP-33222 CHEBI:41423
    CHEMBL118 CJ-016377 CP-598107
    CPD000550473 CS-0570 CTK8H4475
    Celebra Celebrex Celebrex (TN)
    Celebrex, Celebra, 169590-42-5 Celecox Celecoxi
    Celecoxib (JAN/USAN/INN) Celecoxib (SC-58635) Celecoxib 1.0 mg/ml in Acetonitrile
    Celecoxib [USAN:INN:BAN] Celecoxib [USAN] Celecoxib, >=98% (HPLC)
    Celecoxib, European Pharmacopoeia (EP) Reference Standard Celecoxib, Pharmaceutical Secondary Standard Celecoxib, United States Pharmacopeia (USP) Reference Standard
    Celecoxib/Celebrex, Celebra Celecoxibum Celocoxib
    Certified Reference Material D00567 DB00482
    DSSTox_CID_2777 DSSTox_GSID_22777 DSSTox_RID_76725
    DTXSID0022777 DivK1c_000893 EBD24636
    EX-A175 FT-0080064 FT-0601628
    FT-0623536 FT-0700357 GTPL2892
    HMS1922G14 HMS2089L18 HMS2093I07
    HMS2234N18 HMS3259L08 HMS3261A14
    HMS3373A09 HMS3654H09 HMS3715F11
    HMS502M15 HSDB 7038 HY-14398
    IDI1_000893 J-010566 J-520011
    J10035 JCX84Q7J1L KBio1_000893
    KBio2_000912 KBio2_002351 KBio2_003480
    KBio2_004919 KBio2_006048 KBio2_007487
    KBio3_002830 KBio3_003037 KBioGR_000723
    KBioGR_002351 KBioSS_000912 KBioSS_002354
    KS-00000FW2 KS-1041 LS-31667
    MCULE-4750749400 MFCD00941298 MLS001165684
    MLS001195656 MLS001304708 MLS006011862
    NC00708 NCGC00091455-01 NCGC00091455-02
    NCGC00091455-03 NCGC00091455-04 NCGC00091455-05
    NCGC00091455-06 NCGC00091455-07 NCGC00091455-08
    NCGC00091455-09 NCGC00091455-13 NCGC00254540-01
    NCGC00259513-01 NCGC00261091-01 NCI60_041049
    NINDS_000893 NSC-719627 NSC-758624
    NSC719627 NSC758624 Onsenal
    Onsenal (TN) PF-00345549 PHA-00846533
    Pharmakon1600-01503678 Q-200816 Q408801
    RZEKVGVHFLEQIL-UHFFFAOYSA-N SAM002589995 SB19318
    SBI-0051875.P002 SC 58635 SC-50829
    SC-58553, SC-58635 SC-58635 SC58635
    SCHEMBL3708 SMR000550473 SPBio_001512
    SPECTRUM1503678 SR-01000837528 SR-01000837528-2
    SR-01000837528-3 STL373576 SW199611-3
    SYN3015 Solexa Spectrum2_001576
    Spectrum3_001996 Spectrum4_000182 Spectrum5_001324
    Spectrum_000432 TPI-336 Tox21_111135
    Tox21_111135_1 Tox21_201964 Tox21_300599
    Tox21_500406 UNII-JCX84Q7J1L UNM-0000305813
    US8741944, Comparative Compound Xilebao YM 177
    YM-177 YM177 Z2210694606
    ZINC2570895 benzenesulfonamide, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]- cMAP_000027
    celecoxib cid_2662 p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide
    s1261

    DrugBank Name Celecoxib
    DrugBank DB00482
    CAS Number 1000343-91-8, 169590-42-5, 184007-95-2, 194044-54-7
    PubChem Compound 2662
    KEGG Compound ID C07589
    KEGG Drug D00567
    PubChem.Substance 46505596
    ChEBI 41423
    PharmGKB PA448871
    ChemSpider 2562
    BindingDB 11639.0
    TTD DAP000737
    Wikipedia Celecoxib
    HET CEL
    DPD 11865

    1. Dykens et al. (2007)