PIRPROFEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H14ClNO2
Molecular Weight	251.709
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC(Cl)=C(C=C1)N2CC=CC2

InChI

InChIKey=PIDSZXPFGCURGN-UHFFFAOYSA-N

InChI=1S/C13H14ClNO2/c1-9(13(16)17)10-4-5-12(11(14)8-10)15-6-2-3-7-15/h2-5,8-9H,6-7H2,1H3,(H,16,17)

HIDE SMILES / InChI

Molecular Formula	C13H14ClNO2
Molecular Weight	251.709
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://books.google.ru/books?id=leVCukUgNlsC&pg=PA188&lpg=PA188&dq=PIRPROFEN retrieved from Consolidated List of Products Whose Consumption and or Sale Have Been Banned Withdrawn Severely Restricted or Not Approved By Governments: Chemicals. By United Nations, p.188 | https://www.ncbi.nlm.nih.gov/pubmed/6360612 | https://www.ncbi.nlm.nih.gov/pubmed/3539573

Pirprofen is a non-steroidal anti-inflammatory drug, related structurally to drugs such as ibuprofen, ketoprofen and naproxen. Pirprofen was introduced by Ciba-Geigy in 1982 as a treatment for rheumatic diseases. In 1990 due to adverse effects, including some cases of fatal liver toxicity the manufacturers decided to discontinue marketing it worldwide. Pirprofen proved to be useful in the management of both rheumatoid arthritis and osteoarthritis and as an analgesic. In doses of 600-800 mg/d, pirprofen has been found to be as effective as, but not superior to, aspirin 3.6 g/d in relieving the more common symptoms of rheumatoid arthritis. Pirprofen is as effective as, but not superior to, other available NSAIDs in terms of efficacy, tolerability, and incidence of adverse effects. The recommended dosage in osteoarthritis is 450-600 mg/d.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pirprofen and aspirin in the treatment of rheumatoid arthritis.	1979 May	373942
Pirprofen-induced fulminant hepatitis.	1985 Jul	4007406
[Cholestatic and cytolytic hepatitis and acute kidney failure caused by pirprofen].	1986	3813277
[Hepatitis due to pirprofen; 3 cases, 1 fatality].	1986 Jan-Feb	2938537
[Interstitial nephropathy with nephrotic syndrome induced by pirprofen].	1986 Nov	3809790
Remission of severe rheumatoid arthritis following liver transplantation.	1993 Sep	8369897
A recombinant phenobarbital-inducible rat liver UDP-glucuronosyltransferase (UDP-glucuronosyltransferase 2B1) stably expressed in V79 cells catalyzes the glucuronidation of morphine, phenols, and carboxylic acids.	1994 Jan	8302279
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.	2003 Jul	12829995
A peripatetic pediatrician's journey into pediatric rheumatology: Part II.	2007 Jun 21	17584931
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery.	2008 Oct 31	18972594
Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs.	2009 Sep	19740398

Patents

Sample Use Guides

In Vivo Use Guide

Published clinical trials indicate that pirprofen 600 to 1200 mg/day as 2 or 3 divided doses is a suitable alternative to usual therapeutic dosages of aspirin, flurbiprofen, ibuprofen, indomethacin, ketoprofen, naproxen, piroxicam and sulindac in the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, musculoskeletal disorders and non-articular rheumatism. In patients with acute postsurgical, trauma or cancer pain, single oral or intramuscular doses of pirprofen 200 to 400mg provide equivalent analgesic activity to usual therapeutic doses of aspirin, diflunisal, ketoprofen, noramidopyrine, paracetamol and pentazocine.

Route of Administration: Other

In Vitro Use Guide

The compound proved to be a potent inhibitor with a Ki value of about 1.2 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:15:04 UTC 2023` Edited by `admin` on `Fri Dec 15 17:15:04 UTC 2023`
Record UNII	T7KN291890
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIRPROFEN

Official Name

English

PIRPROFEN [MI]

Common Name

English

RANGASIL 400

Common Name

English

3-Chloro-4-(3-pyrrolin-1-yl)hydratropic acid

Systematic Name

English

SU 21524

Code

English

RACEMIC PIRPROFEN

Common Name

English

SU-21524

Code

English

2-(3-CHLORO-4-(2,5-DIHYDROPYRROL-1-YL)-PHENYL)PROPANOIC ACID

Systematic Name

English

2-(3-CHLORO-4-(3-PYRROLIN-1-YL)PHENYL)PROPIONIC ACID

Systematic Name

English

PIRPROFEN [USAN]

Common Name

English

Pirprofen [WHO-DD]

Common Name

English

BENZENEACETIC ACID, 3-CHLORO-4-(2,5-DIHYDRO-1H-PYRROL-1-YL)-.ALPHA.-METHYL-

Common Name

English

RENGASIL

Common Name

English

(±)-PIRPROFEN

Common Name

English

HYDRATROPIC ACID, 3-CHLORO-4-(3-PYRROLIN-1-YL)-

Common Name

English

pirprofen [INN]

Common Name

English

PIRPROFEN [MART.]

Common Name

English

SEFLENYL

Brand Name

English

PIRPROFEN [JAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM01AE08