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Drug

D0088 | Naproxen

Molecular Formula C14H14O3
Molecular Weight 230.26
Structure
State solid
Clearance Naproxen is cleared at a rate of 0.13 mL/min/kg.[L6582][L6583]
Volume of distribution Naproxen has a volume of distribution of 0.16 L/kg.[L6582][L6583]
Route of elimination After oral administration, about 95% of naproxen and it's metabolites can be recovered in the urine with 66-92% recovered as conjugated metabolite and less than 1% recovered as naproxen or desmethylnaproxen.[A179197][L6582][L6583] Less than 5% of naproxen is excreted in the feces.[L6582][L6583]
Protein binding Naproxen is highly protein bound with >99% of the drug bound to albumin at therapeutic levels.[L6582][L6583]
Half life The half-life of naproxen is reported to be 12-17 hours.[A178975]
Absorption Naproxen is available as a free acid and sodium salt.[A179098] At comparable doses, (naproxen 500 mg = naproxen sodium 550 mg) they differ slightly in their rates of absorption, but otherwise they are therapeutically and pharmacologically equivalent.[A179098] Naproxen sodium achieves a peak plasma concentration after 1 hour, while peak plasma concentration is observed after 2 hours with naproxen (free acid).[A179098] There are no differences between the 2 forms in the post-absorption phase pharmacokinetics.[A179098] The difference in initial absorption should be considered when treating acute pain, since naproxen sodium may offer a quicker onset of action.[A179098] Overall, naproxen is rapidly and completely absorbed when administered orally and rectally.[A179110][A179098] Food may contribute to a delay in the absorption of orally administered naproxen, but will not affect the extent of absorption.[A179098]
Trade names Aleve
Description nonsteroidal anti-inflammatory drug (NSAID) ; nonselective COX inhibitor; propionic acid class

G

M

M02AA12 Naproxen


[M02AA] Antiinflammatory preparations, non-steroids for topical use


[M02A] TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN


[M02] TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN


[M] Musculoskeletal system

M01AE56 Naproxen and misoprostol


[M01AE] Propionic acid derivatives


[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS


[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS


[M] Musculoskeletal system

M01AE52 Naproxen and esomeprazole


[M01AE] Propionic acid derivatives


[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS


[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS


[M] Musculoskeletal system

M01AE02 Naproxen


[M01AE] Propionic acid derivatives


[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS


[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS


[M] Musculoskeletal system

G02CC02 Naproxen


[G02CC] Antiinflammatory products for vaginal administration


[G02C] OTHER GYNECOLOGICALS


[G02] OTHER GYNECOLOGICALS


[G] Genitourinary system and reproductive hormones

Toxicity Dose Time Species Model Method Action Positive criterion Reference
PROTONOPHORIC UNCOUPLING 278

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 126 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 1 of 126 companies. For more detailed information, please visit ECHA C&L website


Of the 21 notification(s) provided by 125 of 126 companies with hazard statement code(s):


H301 (46.4%): Toxic if swallowed [Danger Acute toxicity, oral]


H302 (54.4%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (52%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (52%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (49.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (48%): Suspected of damaging fertility or the unborn child [Warning 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, P261, P264, P270, P271, P280, P281, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Warning

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.


H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


 P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Abdominal discomfort

  • Ankylosing spondylitis

  • Body temperature increased

  • Fibromyalgia

  • Gastrointestinal haemorrhage

  • Gouty arthritis

  • Headache

  • Inflammation

  • Joint swelling

  • Juvenile idiopathic arthritis

  • Ligament sprain

  • Muscle spasms

  • Musculoskeletal disorder

  • Musculoskeletal stiffness

  • Nasopharyngitis

  • Nephropathy

  • Osteoarthritis

  • Procedural pain

  • Rheumatic disorder

  • Rheumatoid arthritis

  • Rhinitis

  • Rotator cuff syndrome

  • Spinal osteoarthritis

  • Spondylitis

  • Tendonitis

  • Toothache

  • Ulcer

  • Uterine pain

  • Vasculitis

  • Asthenia (0)

  • Influenza (0.1)

    • (+)(S)2-(6-methoxy-2-naphthyl)-propionic acid (+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid (+)-(S)-Naproxen
    (+)-2-(6-Methoxy-2-naphthyl)propionic acid (+)-2-(Methoxy-2-naphthyl)-propionic acid (+)-2-(Methoxy-2-naphthyl)-propionsaeure
    (+)-2-(Methoxy-2-naphthyl)-propionsaeure [German] (+)-2-(Methoxy-2-naphthyl)-propionsaure (+)-6-Methoxy-.alpha.-methyl-2-naphthaleneacetic acid
    (+)-6-Methoxy-.alpha.-methyl-2-napthaleneacetic acid (+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid (+)-Naproxen
    (+)NAPROXEN (2S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid (2S)-2-(6-methoxy(2-naphthyl))propanoic acid
    (2S)-2-(6-methoxy-2-naphthyl)propanoic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid
    (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid (S)-(+)-2-(6-methoxy-naphthalen-2-yl)-propionic acid (S)-(+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid
    (S)-(+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid, 98% (S)-(+)-Naproxen (S)-(+)-Naproxene
    (S)-2-(6-Methoxy-2-naphthyl)propanoic acid (S)-2-(6-Methoxy-2-naphthyl)propionic acid (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid
    (S)-2-(6-methoxy-2-naphthyl)-propionic acid (S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (S)-6-Methoxy-.alpha.-methyl-2-naphthalene acetic acid
    (S)-6-Methoxy-.alpha.-methyl-2-naphthaleneacetic acid (S)-6-Methoxy-?-methyl-2-naphthaleneacetic Acid (S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid
    (S)-Naproxen (alphas)-6-methoxy-alpha-methyl-2-naphthaleneacetic acid (s)-(+)-6-methoxy-alpha-methyl-2-naphthalene acetic acid
    04N531 2-(6-Methoxy-2-naphthyl)propanoic acid , (+)- 2-(6-Methoxy-naphthalen-2-yl)-propionic acid(Naproxen)
    2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (+)- 2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (.alpha.S)- 2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (S)-
    2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)- 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)- (8CI) 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (S)-
    22204-53-1 26159-31-9 4or0
    4po0 57Y76R9ATQ AB00052049-04
    AB00052049_05 AB1009325 AC-1363
    ACT02593 AKOS005267223 AM20060551
    ANW-24773 ARONIS24306 Acusprain
    Aleve Anaprox Anax
    Anexopen Apo-Napro-NA Apo-Naproxen
    Apronax Artagen Arthrisil
    Artrixen Artroxen Atiflan
    Axer BDBM50339185 BIDD:GT0062
    BR-72928 BRD-K59197931-001-02-9 BRD-K59197931-001-03-7
    BRD-K59197931-236-09-6 BSPBio_002067 Bipronyl
    Bonyl C01517 CAS-22204-53-1
    CCG-40130 CCRIS 5265 CG 3117
    CHEBI:7476 CHEMBL154 CMWTZPSULFXXJA-VIFPVBQESA-
    CMWTZPSULFXXJA-VIFPVBQESA-N CS-2163 CTK8B1225
    Calosen Certified Reference Material Clinosyn
    Congex D00118 DB00788
    DL Naproxen DSSTox_CID_20686 DSSTox_GSID_40686
    DSSTox_RID_79542 DTXSID4040686 Danaprox
    Daprox Diocodal DivK1c_000242
    Duk Dysmenalgit Dysmenalgit N
    EC 244-838-7 EINECS 244-838-7 Ec-Naprosyn
    Epitope ID:139974 Equiproxen Equiproxen (Veterinary)
    FT-0082415 FT-0602835 Flanax Forte
    Flexen Flexipen Floginax
    Fuxen GTPL5230 Genoxen
    HMS1920P13 HMS2089N21 HMS2091H12
    HMS3649M13 HMS500M04 HSDB 3369
    HY-15030 Headlon IDI1_000242
    InChI=1/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1 J10145 KBio1_000242
    KBio2_001457 KBio2_004025 KBio2_006593
    KBio3_001567 KBioGR_000597 KBioSS_001457
    KS-00002WWU KSC911E2L LS-124738
    Laraflex Laser Lefaine
    Leniartil Lopac0_000792 M-5280
    M1021 MCULE-2589082817 ME-0100
    MFCD00010500 Methoxypropiocin Mnpa
    NAPROXEN NCGC00016759-01 NCGC00016759-02
    NCGC00016759-03 NCGC00021127-01 NCGC00161591-01
    NCGC00255562-01 NINDS_000242 NPS
    NSC-750183 NSC-757239 NSC750183
    NSC757239 Nafasol Naixan
    Nalyxan Napflam Napmel
    Naposin Napratec Napren
    Napren E Naprius Naprolag
    Naprontag Naprosin Naprosine
    Naprosy Naprosyn Naprosyn (TN)
    Naprosyn LLE Naprosyn LLE Forte Naprosyne
    Naproxen Naproxen (JP17/USP/INN) Naproxen 1.0 mg/ml in Methanol
    Naproxen [USAN:BAN:INN:JAN] Naproxen [USAN:USP:INN:BAN:JAN] Naproxen solution 1.0 mg/ml in methanol
    Naproxen solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material Naproxen, British Pharmacopoeia (BP) Reference Standard Naproxen, European Pharmacopoeia (EP) Reference Standard
    Naproxen, Pharmaceutical Secondary Standard Naproxen, United States Pharmacopeia (USP) Reference Standard Naproxen, VETRANAL(TM), analytical standard
    Naproxen, meets USP testing specifications Naproxen,(S) Naproxen2-(6-Methoxy-naphthalen-2-yl)-propionic acid
    Naproxene Naproxene [INN-French] Naproxeno
    Naproxeno [INN-Spanish] Naproxenum Naproxenum [INN-Latin]
    Naproxi 250 Naproxi 500 Napxen
    Narma Narocin Naxen
    Naxen F Naxopren Naxyn
    Naxyn 250 Naxyn 500 Noflam
    Novonaprox Nycopren Panoxen
    Patxen Pharmakon1600-01500425 Prafena
    Prestwick0_000791 Prestwick1_000791 Prestwick2_000791
    Prestwick_349 Prexan Priaxen
    Pronaxen Propionic acid, 2-(6-methoxy-2-naphthyl)-, (+)- Proxen LE
    Proxen LLE Proxine PubChem8102
    Q-201447 Q1215575 RS 3540
    RS-3540 RTR-010461 Rahsen
    Reuxen Rheumaflex Roxen
    SBI-0050769.P004 SC-02561 SCHEMBL3046
    SPBio_000966 SPBio_002861 SPECTRUM1500425
    SR-01000003110 SR-01000003110-5 SR-01000075977
    SR-01000075977-10 SR-01000075977-3 SR-01000075977-4
    ST2408284 Saritilron Sinartrin
    Sinton Soproxen Spectrum2_001043
    Spectrum3_000514 Spectrum4_000069 Spectrum5_001327
    Spectrum_000977 Sutolin Sutony
    Tohexen Tox21_301953 Traumox
    U-Ritis UNII-57Y76R9ATQ UPCMLD-DP001
    UPCMLD-DP001:001 Velsay Veradol
    Vinsen W4580 Xenar
    Xenar-CR ZINC105216 d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure
    d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure [German] d-2-(6-Methoxy-2-naphthyl)propionic Acid d-2-(6-Methoxy-2-naphthyl)propionic acid
    d-Naproxen d-Naproxen naproxen(+)

    DrugBank Name Naproxen
    DrugBank DB00788
    CAS Number 131991-52-1, 22204-53-1, 23979-41-1, 26159-31-9, 51091-84-0
    PubChem Compound 156391
    KEGG Compound ID C01517
    KEGG Drug D00118
    PubChem.Substance 46505508
    ChEBI 7476
    PharmGKB PA450595
    ChemSpider 137720
    BindingDB 50339185.0
    TTD DAP000968
    Wikipedia Naproxen
    HET NPS
    DPD 2037|2414

    1. Chan et al. (2005)
    2. Dykens et al. (2007)