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Substance Name: Naproxen [USAN:USP:INN:BAN:JAN]
RN: 22204-53-1
UNII: 57Y76R9ATQ
InChIKey: CMWTZPSULFXXJA-VIFPVBQESA-N

Note

  • An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.

Molecular Formula

  • C14-H14-O3

Molecular Weight

  • 230.2616
 

Classification Codes

  • Analgesic
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antipyretic
  • Antirheumatic Agents
  • Antiviral (COVID-19)
  • Cyclooxygenase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Gout Suppressants
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
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Names and Synonyms

Name of Substance

  • Naproxen
  • Naproxen [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Naproxen

Synonyms

  • (+)-(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]
  • (+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid
  • (+)-Naproxen
  • (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid
  • (S)-(+)-Naproxen
  • (S)-2-(6-Methoxy-2-naphthyl)propanoic acid
  • (S)-2-(6-Methoxy-2-naphthyl)propionic acid
  • (S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid
  • (S)-Naproxen
  • 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)-
  • Acusprain
  • Anax
  • Anexopen
  • Apo-Napro-Na
  • Apo-Naproxen
  • Apronax
  • Artagen
  • Arthrisil
  • Artrixen
  • Artroxen
  • Atiflan
  • Axer
  • Bipronyl
  • Bonyl
  • Calosen
  • CCRIS 5265
  • CG 3117
  • Clinosyn
  • Congex
  • d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure
  • d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure [German]
  • d-2-(6-Methoxy-2-naphthyl)propionic acid
  • d-Naproxen
  • Danaprox
  • Daprox
  • Duk
  • Dysmenalgit N
  • EC 244-838-7
  • Ec-Naprosyn
  • EINECS 244-838-7
  • Equiproxen
  • Equiproxen (Veterinary)
  • Flanax Forte
  • Flexen
  • Flexipen
  • Fuxen
  • Genoxen
  • Headlon
  • HSDB 3369
  • Laraflex
  • Lefaine
  • Leniartil
  • Nafasol
  • Naixan
  • Nalyxan
  • Napflam
  • Napmel
  • Naposin
  • Napratec
  • Napren
  • Napren E
  • Naprius
  • Naprontag
  • Naprosyn
  • Naprosyn LLE
  • Naprosyn LLE Forte
  • Naprosyne
  • Naproxen
  • Naproxene
  • Naproxene [INN-French]
  • Naproxeno
  • Naproxeno [INN-Spanish]
  • Naproxenum
  • Naproxenum [INN-Latin]
  • Naproxi 250
  • Naproxi 500
  • Napxen
  • Narma
  • Narocin
  • Naxen
  • Naxen F
  • Naxid
  • Naxopren
  • Naxyn
  • Naxyn 250
  • Naxyn 500
  • Noflam
  • Novonaprox
  • NSC 750183
  • NSC 757239
  • Nycopren
  • Patxen
  • Prafena
  • Priaxen
  • Pronaxen
  • Proxen LE
  • Proxen LLE
  • Rahsen
  • Reuxen
  • Rheumaflex
  • Roxen
  • RS 3540
  • RS-3540
  • Saritilron
  • Sinartrin
  • Sinton
  • Soproxen
  • Sutolin
  • Sutony
  • Tohexen
  • Traumox
  • U-Ritis
  • UNII-57Y76R9ATQ
  • Velsay
  • Veradol
  • Vinsen
  • Xenar
  • Xenar-CR

Systematic Names

  • 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)-
  • 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (S)-
  • Naproxen
  • Propionic acid, 2-(6-methoxy-2-naphthyl)-, (+)-

Registry Numbers

CAS Registry Number

  • 22204-53-1

FDA UNII

  • 57Y76R9ATQ

System Generated Number

  • 0022204531

Structure Descriptors

InChI

InChI=1S/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

InChIKey

CMWTZPSULFXXJA-VIFPVBQESA-N

Smiles

COc1ccc2cc(ccc2c1)[C@H](C)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 2250mg/kg/26W (2250mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Journal of Rheumatology. Vol. 26, Pg. 210, 1987.
dog LD50 oral > 1gm/kg (1000mg/kg)   Yakkyoku. Pharmacy. Vol. 29, Pg. 861, 1978.
dog LD50 unreported 1gm/kg (1000mg/kg)   Journal of Clinical Pharmacology. Vol. 15, Pg. 311, 1975.
guinea pig LD50 oral 665mg/kg (665mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster LD50 oral 1400mg/kg (1400mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster LD50 unreported 4110mg/kg (4110mg/kg)   Journal of Clinical Pharmacology. Vol. 15, Pg. 311, 1975.
man TDLo oral 54mg/kg (54mg/kg) KIDNEY, URETER, AND BLADDER: PROTEINURIS

GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 173, 1995.
man TDLo oral 114mg/kg/10D- (114mg/kg) BLOOD: CHANGES IN PLATELET COUNT Journal of Clinical Pharmacology. Vol. 40, Pg. 124, 2000.
man TDLo oral 214mg/kg/30D- (214mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

LIVER: OTHER CHANGES

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"		 Postgraduate Medical Journal. Vol. 56, Pg. 368, 1980.
man TDLo oral 3429mg/kg/35W (3429mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Postgraduate Medical Journal. Vol. 68, Pg. 766, 1992.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   Bollettino Chimico Farmaceutico. Vol. 119, Pg. 600, 1980.
mouse LD50 intravenous 435mg/kg (435mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Journal of Pharmacology and Experimental Therapeutics. Vol. 179, Pg. 114, 1971.
mouse LD50 oral 360mg/kg (360mg/kg)   Farmaco, Edizione Scientifica. Vol. 40, Pg. 334, 1985.
mouse LD50 subcutaneous 475mg/kg (475mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1039, 1972.
mouse LD50 unreported 1234mg/kg (1234mg/kg)   Journal of Clinical Pharmacology. Vol. 15, Pg. 311, 1975.
rat LD50 intraperitoneal 354mg/kg (354mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 829, 1978.
rat LD50 oral 248mg/kg (248mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 41, Pg. 1265, 1991.
rat LD50 subcutaneous 928mg/kg (928mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 1272, 1983.
women LDLo oral 200mg/kg/10D- (200mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 American Journal of Hematology. Vol. 58, Pg. 142, 1998.
women TDLo oral 40mg/kg/2D-I (40mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Scandinavian Journal of Rheumatology. Vol. 15, Pg. 401, 1986.
women TDLo oral 70mg/kg/W-I (70mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" New England Journal of Medicine. Vol. 295, Pg. 1201, 1976.
women TDLo oral 126mg/kg/3W-I (126mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: EOSINOPHILIA

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"		 Japanese Journal of Medicine. Vol. 30, Pg. 32, 1991.
women TDLo oral 315mg/kg/3W-I (315mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: EXCITEMENT		 American Journal of Medicine. Vol. 89, Pg. 526, 1990.
women TDLo oral 900mg/kg/9W-I (900mg/kg) SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE Medical Journal of Australia. Vol. 151, Pg. 167, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 153 deg C   EXP
pKa Dissociation Constant 4.15 (none)   EXP
log P (octanol-water) 3.18 (none)   EXP
Water Solubility 15.9 mg/L 25 EXP
Vapor Pressure 1.89E-06 mm Hg 25 EST
Henry's Law Constant 3.39E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.16E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.