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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C14H14O3.C4H10N2
Molecular Weight 546.6539
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPROXEN PIPERAZINE

SMILES

C1CNCCN1.COC2=CC3=CC=C(C=C3C=C2)[C@H](C)C(O)=O.COC4=CC5=CC=C(C=C5C=C4)[C@H](C)C(O)=O

InChI

InChIKey=KRDCGZGYWRCHNN-NAWJVIAPSA-N
InChI=1S/2C14H14O3.C4H10N2/c2*1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10;1-2-6-4-3-5-1/h2*3-9H,1-2H3,(H,15,16);5-6H,1-4H2/t2*9-;/m00./s1

HIDE SMILES / InChI

Molecular Formula C4H10N2
Molecular Weight 86.1356
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H14O3
Molecular Weight 230.2592
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Naproxen (naproxen sodium, NAPROSYN®) is a propionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). It is 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. The mechanism of action of the naproxen (naproxen sodium, NAPROSYN®), like that of other NSAIDs, is not completely understood but involves inhibition of cyclooxygenase (COX-1 and COX-2).

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of clopidogrel on naproxen-induced gastrointestinal blood loss in healthy volunteers.
1998
Renal effects of selective cyclooxygenase-2 inhibition in normotensive salt-depleted subjects.
1999 Jul
Low-dose diclofenac, naproxen, and ibuprofen cohort study.
1999 Jul
Renal changes associated with naproxen sodium administration in cynomolgus monkeys.
1999 May-Jun
Long-term followup of naproxen-induced pseudoporphyria in juvenile rheumatoid arthritis.
1999 Oct
Persistent pulmonary hypertension after maternal naproxen ingestion in a term newborn: a case report.
2000
[Aspirin-induced angioedema of the nape of the neck with naproxen cross-reaction: a case report].
2000 May
Synthesis of some new 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones and their anti-inflammatory activities.
2001
[Two complex suicidal poisonings with drugs and their medicolegal aspects].
2001
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.
2001 Apr
[Acupuncture contra antiphlogistics in acute lumbago].
2001 Apr 20
I'm taking over-the-counter ibuprofen every day for neck pain. Recently, my doctor gave me a prescription for naproxen for my arthritis. Should I be concerned about taking these two together?
2001 Aug
Time and dose dependent augmentation of inhibitory effects of abciximab by aspirin.
2001 Feb
A look at the safety profile of over-the-counter naproxen sodium: a meta-analysis.
2001 Feb
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2.
2001 Feb
Rhein, an active metabolite of diacerein, suppresses the interleukin-1alpha-induced proteoglycan degradation in cultured rabbit articular chondrocytes.
2001 Jan
Prostaglandin H synthase-2 inhibitors interfere with prostaglandin H synthase-1 inhibition by nonsteroidal anti-inflammatory drugs.
2001 Jan 19
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes.
2001 Jun
Determination of naproxen in pharmaceutical preparations by room-temperature phosphorescence. A comparative study of several organized media.
2001 Jun
Treatment of de Quervain's disease:role of conservative management.
2001 Jun
[Nitric oxide and gastroduodenal damage caused by NSAIDs. Recent findings and clinical implications].
2001 Mar
Interleukin-6 (IL-6) producing phaeochromocytoma: direct IL-6 suppression by non-steroidal anti-inflammatory drugs.
2001 Mar
Anti-lymphoma effect of naproxen and indomethacin in a patient with relapsed diffuse large B-cell lymphoma.
2001 Mar
High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.
2001 Mar
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.
2001 Mar
Functional status and health-related quality of life of elderly osteoarthritic patients treated with celecoxib.
2001 Mar
Is rofecoxib safer than naproxen?
2001 Mar
Rofecoxib, a COX-2 inhibitor, does not inhibit human gastric mucosal prostaglandin production.
2001 Mar
Effect of antipyretic drugs in children with malaria.
2001 Mar 1
Prostaglandin biosynthesis by fat body from true armyworms, Pseudaletia unipuncta.
2001 Mar 15
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.
2001 Mar 16
Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen.
2001 Mar 29
Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives.
2001 May
[The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%].
2001 May
Nimesulide reduces interleukin-1beta-induced cyclooxygenase-2 gene expression in human synovial fibroblasts.
2001 May
Upper gastrointestinal toxicity of rofecoxib and naproxen.
2001 May 3
Isotachophoretic determination of naproxen in the presence of its metabolite in human serum.
2001 May 4
Patents

Sample Use Guides

In Vivo Use Guide
Rheumatoid Arthritis, Osteoarthritis and Ankylosing Spondylitis: 1 tablet of NAPROSYN® (250 mg or 375 mg or 500 mg) twice daily. Acute Gout: The recommended starting dose is 750 mg of NAPROSYN® followed by 250 mg every 8 hours until the attack has subsided.
Route of Administration: Oral
In Vitro Use Guide
There are data on the N-(3-methylpyridin-2-yl)amide derivatives of flurbiprofen and naproxen (Flu-AM1 and Nap-AM1, respectively) with respect to their properties towards fatty acid amide hydrolase (FAAH). Flu-AM1 and Nap-AM1 inhibited FAAH-catalysed hydrolysis of [(3)H]anandamide by rat brain homogenates with IC50 values of 0.44 and 0.74 uM. The corresponding values for flurbiprofen and naproxen were 29 and >100 uM, respectively.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:35:26 UTC 2019
Edited
by admin
on Tue Oct 22 00:35:26 UTC 2019
Record UNII
R2A8B8HIPI
Record Status Validated (UNII)
Record Version
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Name Type Language
NAPROXEN PIPERAZINE
WHO-DD  
Common Name English
NAPROXEN PIPERAZINE [WHO-DD]
Common Name English
NAPROXEN PIPERAZINE SALT
MI  
Common Name English
(S)-6-METHOXY-.ALPHA.-METHYLNAPHTHALENE-2-ACETIC ACID, COMPOUND WITH PIPERAZINE (2:1)
Common Name English
NAPROXEN PIPERAZINE SALT [MI]
Common Name English
PIPROXEN
Common Name English
Code System Code Type Description
CAS
70981-66-7
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY
PUBCHEM
76968825
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY
MERCK INDEX
M7769
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY Merck Index
EPA CompTox
70981-66-7
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY
ECHA (EC/EINECS)
275-083-1
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY
EVMPD
SUB14897MIG
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY
MESH
C504545
Created by admin on Tue Oct 22 00:35:26 UTC 2019 , Edited by admin on Tue Oct 22 00:35:26 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY