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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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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Other Resources (Internet Locators)
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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/s1InChIKey
CMWTZPSULFXXJA-VIFPVBQESA-NSmiles
COc1ccc2cc(ccc2c1)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.