ChemFOnt: Showing chemical card for Naproxen (CFc000001281)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:53 UTC

Chemfont ID

CFc000001281

Molecule Identification

Common Name

Naproxen

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid	ChEBI
(+)-(S)-Naproxen	ChEBI
(+)-2-(6-Methoxy-2-naphthyl)propionic acid	ChEBI
(+)-2-(Methoxy-2-naphthyl)-propionic acid	ChEBI
(+)-2-(Methoxy-2-naphthyl)-propionsaeure	ChEBI
(+)-Naproxen	ChEBI
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid	ChEBI
(S)-(+)-Naproxen	ChEBI
(S)-2-(6-Methoxy-2-naphthyl)propanoic acid	ChEBI
(S)-2-(6-Methoxy-2-naphthyl)propionic acid	ChEBI
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid	ChEBI
(S)-Naproxen	ChEBI
Naproxene	ChEBI
Naproxeno	ChEBI
Naproxenum	ChEBI
Naprosyn	Kegg
(+)-(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-α-methyl-2-naphthaleneacetate	Generator
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid	Generator
(+)-2-(6-Methoxy-2-naphthyl)propionate	Generator
(+)-2-(Methoxy-2-naphthyl)-propionate	Generator
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionate	Generator
(S)-2-(6-Methoxy-2-naphthyl)propanoate	Generator
(S)-2-(6-Methoxy-2-naphthyl)propionate	Generator
(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-α-methyl-2-naphthaleneacetate	Generator
(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid	Generator
2-(6-Methoxy-2-naphthyl)propionic acid	HMDB
Acusprain	HMDB
Anexopen	HMDB
Apronax	HMDB
Artagen	HMDB
Arthrisil	HMDB
Artrixen	HMDB
Artroxen	HMDB
Atiflan	HMDB
Axer	HMDB
Bipronyl	HMDB
Calosen	HMDB
Clinosyn	HMDB
Congex	HMDB
D-Naproxen	HMDB
Danaprox	HMDB
Daprox	HMDB
Diocodal	HMDB
DL Naproxen	HMDB
DL-Naproxen	HMDB
Duk	HMDB
Dysmenalgit	HMDB
Dysmenalgit N	HMDB
Ec-naprosyn	HMDB
Equiproxen	HMDB
Flexipen	HMDB
Floginax	HMDB
Fuxen	HMDB
Genoxen	HMDB
Lefaine	HMDB
Leniartil	HMDB
Nafasol	HMDB
Naixan	HMDB
Nalyxan	HMDB
Napflam	HMDB
Napmel	HMDB
Naposin	HMDB
Naprosyne	HMDB
Naproxen sodium	HMDB
Novonaprox	HMDB
Nycopren	HMDB
Opipramol	HMDB
Anaprox	HMDB
Methoxypropiocin	HMDB
Naprosin	HMDB
Proxen	HMDB
Aleve	HMDB
Sodium, naproxen	HMDB
MNPA	HMDB
Synflex	HMDB
Naproxenate, sodium	HMDB
Sodium naproxenate	HMDB

Chemical Formula

C₁₄H₁₄O₃

Average Molecular Weight

230.2592

Monoisotopic Molecular Weight

230.094294314

IUPAC Name

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

Traditional Name

naproxen

CAS Registry Number

22204-53-1

SMILES

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

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

Chemical Taxonomy

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11925405)

Cellular substructure

Membrane (HMDB: HMDB0001923)
Cell membrane (HMDB: HMDB0001923)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0001923)

Excreta

Biofluid or Excreta

Feces (PMID: 25037050)

Source

Exogenous

Exogenous (HMDB: HMDB0001923)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Naproxen Action Pathway (HMDB: HMDB0001923)
Naproxen Action Pathway (PathBank: SMP0000120)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001923)

Physical Properties

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