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22204-53-1

Basic Information
CAS No.: 22204-53-1
Name: Naproxen
Molecular Structure:
Molecular Structure of 22204-53-1 (Naproxen)
Formula: C14H14O3
Molecular Weight: 230.26
Synonyms: 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (S)-;Naprontag;(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid;Nafasol;Proxen LE;(+)-2-(Methoxy-2-naphthyl)-propionic acid;Artrixen;Tohexen;Rahsen;(S)-6-Methoxy-.alpha.-methyl-2-naphthaleneacetic acid;(S)-(+)-Naproxen;(S)-2-(6-Methoxy-2-naphthyl)propionic acid;(+)-2-(Methoxy-2-naphthyl)-propionic acid;
EINECS: 244-838-7
Density: 1.197 g/cm3
Melting Point: 152-154 °C(lit.)
Boiling Point: 403.888 °C at 760 mmHg
Flash Point: 154.529 °C
Solubility: Insoluble in water.
Appearance: White or almost white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36/37
Transport Information: UN 2811 6.1/PG 3
PSA: 46.53000
LogP: 3.03650
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Specification

1. Introduction of Naproxen
Naproxen is one kind of white to light yellow crystal powder and belongs to the classes of Carboxylic Acids (Chiral); Chiral Building Blocks; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Intermediates & Fine Chemicals; Pharmaceuticals. The IUPAC name is (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid. In addition, the Classification Code is Analgesic; Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory; Anti-inflammatory agents, non-steroidal; Antipyretic; Antirheumatic Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Gout suppressants; Human Data; Mutation data; Peripheral Nervous System Agents; Reproductive Effect; Sensory System Agents. Naproxen can soluble in organic solvents.

2. Properties of Naproxen
Physical properties about Naproxen are:
(1)ACD/LogP: 2.88; (2)ACD/LogD (pH 5.5): 2.135; (3)ACD/LogD (pH 7.4): 0.347; (4)ACD/BCF (pH 5.5): 16.387; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 158.568; (7)ACD/KOC (pH 7.4): 2.584; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 46.53 Å2; (12)Index of Refraction: 1.609; (13)Molar Refractivity: 66.523 cm3; (14)Molar Volume: 192.25 cm3; (15)Polarizability: 26.372 ×10-24cm3; (16)Surface Tension: 47.465 dyne/cm; (17)Density: 1.198 g/cm3; (18)Flash Point: 154.529 °C; (19)Enthalpy of Vaporization: 69.096 kJ/mol; (20)Boiling Point: 403.888 °C at 760 mmHg.

3. Structure Descriptors of Naproxen
You can still convert the following datas into molecular structure:
(1)SMILES: C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O)O
(2)InChI: 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
(3)InChIKey: CMWTZPSULFXXJA-VIFPVBQEBN
(4)Canonical SMILES: CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
(5)Isomeric SMILES: C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O

4. Toxicity of Naproxen
The toxicity data is as follows:

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) GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: PROTEINURIS

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) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
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) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
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: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: EOSINOPHILIA
Japanese Journal of Medicine. Vol. 30, Pg. 32, 1991.
women TDLo oral 315mg/kg/3W-I (315mg/kg) BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
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.

5. Physical Properties of Naproxen

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

6. Preparation of Naproxen
Naproxen can be prepared by 2-(6-Methoxy-2-naphthyl)propenoic acid. This reaction will need reagent H2, catalyst (+)PF6(-) and solvents methanol and acetone. The reaction time is 2 hours at reaction temperature of 25 °C.

(+)-2-(Methoxy-2-naphthyl)-propionic acid can be prepared by 2-(6-Methoxy-2-naphthyl)propenoic acid

7. Uses of Naproxen
Naproxen can react with 2-bromo-cyclohexanone to get 2-Oxocyclohexyl 2-(6-methoxy-2-naphthyl)propionat. This reaction will need reagent Et3N and solvent acetone. The reaction time is 3 hours by heating. The yield is about 58%.

(+)-2-(Methoxy-2-naphthyl)-propionic acid can react with 2-bromo-cyclohexanone to get 2-Oxocyclohexyl 2-(6-methoxy-2-naphthyl)propionat

8. Safety information of Naproxen
When you are using this chemical, please be cautious about it as the following: This chemical is harmful if swallowed. During using it, wear suitable protective clothing and gloves.

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