METAMIZOLE SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H16N3O4S.Na
Molecular Weight	333.339
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CN(CS([O-])(=O)=O)C1=C(C)N(C)N(C1=O)C2=CC=CC=C2

InChI

InChIKey=DJGAAPFSPWAYTJ-UHFFFAOYSA-M

InChI=1S/C13H17N3O4S.Na/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11;/h4-8H,9H2,1-3H3,(H,18,19,20);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: http://www.un.org/esa/coordination/CL12.pdf

Dipyrone, also known as Metamizole (INN), is an ampyrone sulfonate analgesic, antispasmodic and antipyretic. It was withdrawn from US market in 1977 on the basis of reports of agranulocytosis. Depyrone is still used to treat severe and diffucult for relieving pains of different origin; headache, tooth-ache, pains in the joints, muscles, following traumas and operations, gall and kidney colics, neurites, neuralgias, traumatic cerebrasthenia; inflammation of upper respiratory ways of microbial or virus origin; chorea; febrile states. Mechanism of action of dipyrone is complex. It is believed that dipyrone exerts its action by inhibiting COX-3, and activates opioid and cannabioid systems either itself, or by products of its metabolic degradation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 1 30 Target ID: P23219\|\|\|Q5T7T7 Gene ID: 5742.0 Gene Symbol: PTGS1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12242329	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.actavis.bg/nr/rdonlyres/27cd192d-b3cd-4e81-a7a3-fa80f56bf148/0/neuragin_eng.pdf	Primary		Approved 8429	NEURALGIN Approved Use Severe and diffucult for relieving pains of different origin; headache, tooth-ache, pains in the joints, muscles, following traumas and operations, gall and kidney colics, neurites, neuralgias, traumatic cerebrasthenia; inflammation of upper respiratory ways of microbial or virus origin; chorea; febrile states.
Hyperthermia 5 Sources: http://www.pharmaline.co.il/images/newsletterregistration/teva/07102011/optalgininjdr.pdf	Primary		Approved 8429	OPTALGIN Approved Use Optalgin Injection, by intramuscular administration, is indicated to lower temperature in life-threatening situations, when this cannot be achieved by other means. Hyperthermic patients in critical condition may also be treated in non-hospital environment, under close medical supervision.

PubMed

Title	Date	PubMed
Drug utilization and morbidity statistics for the evaluation of drug safety in Sweden.	1984	6430038
Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships.	1987 Nov	3425858
Modifying effects of a mixture of acetaminophen, aspirin, dipyrone and ethenzamide on a multiorgan initiation model and its carcinogenicity in male F344 rats.	1999 Jan 8	10077225
COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression.	2002 Oct 15	12242329
Effects of celecoxib on acid-challenged gastric mucosa of rats: comparison with metamizol and piroxicam.	2004 Jun	15309881
[Acute intermittent porphyria and oral contraception. Case report].	2006 Mar	16871841
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).	2009 Jun	19617648
Over-expression of the LTC4 synthase gene in mice reproduces human aspirin-induced asthma.	2011 Aug	21429049

Patents

Sample Use Guides

In Vivo Use Guide

Dipyrone was administered orally, as subcutaneous and intramuscular injections (daily dose 0.25-1 g as 50% solution), or by intravenous injection.

Route of Administration: Other

In Vitro Use Guide

Cyclooxygenase activity was measured by the formation of PGE2 after exposure to exogenous 30 μM acid for 10 min. Dipyrone inhibited COX-1 with IC50 350 uM, and COX-3 with IC50 of 52 uM.

Name

Type

Language

METAMIZOLE SODIUM

Official Name

English

SODIUM 1-PHENYL-2,3-DIMETHYL-4-METHYLAMINOPYRAZOLON-N-METHANESULFONATE

Common Name

English

NORAMIDOPYRINE METHANESULFONATE SODIUM

Common Name

English

METAMIZOLE SODIUM [EP IMPURITY]

Common Name

English

SODIUM 1-PHENYL-2,3-DIMETHYL-4-METHYLAMINOPYRAZOLON-N-METHANESULPHONATE

Common Name

English

METAMIZOLUM NATRICUM ANHYDRICUM

Common Name

English

METHANESULFONIC ACID, (ANTIPYRINYLMETHYLAMINO)-, SODIUM SALT

Common Name

English

metamizole sodium [INN]

Common Name

English

NORAMIDOPYRINE METHANESULPHONATE SODIUM

Common Name

English

Metamizole sodium [WHO-DD]

Common Name

English

METAMIZOLE SODIUM (ANHYDROUS)

Common Name

English

DIPYRONE ANHYDROUS

Common Name

English

Classification Tree Code System Code

WHO-ATC

N02BB52