Showing Compound Naproxen (FDB022741)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:54 UTC

Update date

2015-10-09 22:31:18 UTC

Primary ID

FDB022741

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Naproxen

Description

Naproxen (INN) is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, injury (like fractures), menstrual cramps, tendonitis, bursitis, and the treatment of primary dysmenorrhea. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Naprogesic, Naprosyn, Naprelan; Naproxen is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, injury (like fractures), menstrual cramps, tendonitis, bursitis, and the treatment of primary dysmenorrhea. Naproxen and naproxen sodium are marketed under various trade names including: Aleve, Anaprox, Naprogesic, Naprosyn, Naprelan. Naproxen was first marketed as the prescription drug Naprosyn in 1976 and naproxen sodium was first marketed under the trade name Anaprox in 1980. It remains a prescription-only drug in much of the world. The U.S. Food and Drug Administration (FDA) approved the use of naproxen sodium as an over-the-counter (OTC) drug in 1991, where OTC preparations are sold under the trade name Aleve. In Australia, small packets of lower-strength preparations of naproxen sodium are Schedule 2 Pharmacy Medicines; Naproxen is a member of the 2-arylpropionic acid (profen) family of NSAIDs. It is an odorless, white to off-white crystalline substance. It is lipid-soluble, practically insoluble in water with a low pH (below pH 4), while freely soluble in water at 6 pH and above. Naproxen has a melting point of 153 degree centigrade. [HMDB]

CAS Number

22204-53-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetate	Generator
(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acid	Generator
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetate	Generator
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid	ChEBI
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetate	Generator
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid	Generator
(+)-(S)-Naproxen	ChEBI
(+)-2-(6-Methoxy-2-naphthyl)propionate	Generator
(+)-2-(6-Methoxy-2-naphthyl)propionic acid	ChEBI
(+)-2-(Methoxy-2-naphthyl)-propionate	Generator

Showing 1 to 10 of 87 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	3.29	ALOGPS
logP	2.99	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.85 m³·mol⁻¹	ChemAxon
Polarizability	24.81 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H14O3

IUPAC name

(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

InChI Identifier

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

InChI Key

CMWTZPSULFXXJA-VIFPVBQESA-N

Isomeric SMILES

COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O

Average Molecular Weight

230.2592

Monoisotopic Molecular Weight

230.094294314

Classification

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Anisole
Alkyl aryl ether
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:7476 )
methoxynaphthalene (CHEBI:7476 )

Ontology

Disposition

Biological location:

Organ and components:

Subcellular:

Biofluid and excreta:

Blood

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Naproxen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0540-1920000000-dfcdd431a9b1898cd2d2	Spectrum
Predicted GC-MS	Naproxen, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-9840000000-4be264b19923ce29c773	Spectrum
Predicted GC-MS	Naproxen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Naproxen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-001i-0190000000-64cc22cce1238357760e	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0f79-0900000000-17f4e93fda31d93027a1	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0fr6-0900000000-4dd08568cff27d62d867	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0910000000-149b16cac2d80de64d8a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-0900000000-e7dfead967f29853140d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-01b9-0900000000-f5f45cee188a08ef62b1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-0900000000-6c076658da1c69f1b909	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-0900000000-2e1269f26d5b927bca33	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-68cd0c5a3fcc15470c14	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-64e5ecb5632e32f89b2d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0910000000-149b16cac2d80de64d8a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-e7dfead967f29853140d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01b9-0900000000-f5f45cee188a08ef62b1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-6c076658da1c69f1b909	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-2e1269f26d5b927bca33	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-b913db958cba90673250	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-01b9-0900000000-f35f797484d025dc2013	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004l-4900000000-e4dd2dd07b393d508ee4	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0390000000-8bab8d5b4ea21227ea6c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q0-0960000000-f66eabdbaeb345d69ff8	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-0900000000-74f939f129b9072f0315	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0390000000-b9c68cf2920eb7b41eac	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00n0-0950000000-7e56ebeb218436f98f52	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-2910000000-2191f1b5cabc1a005c8c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00n0-0920000000-eca41f81604c83496084	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum