METAMIZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H17N3O4S
Molecular Weight	311.357
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

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Structure Search

SMILES

CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C2=CC=CC=C2

InChI

InChIKey=LVWZTYCIRDMTEY-UHFFFAOYSA-N

InChI=1S/C13H17N3O4S/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)

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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 It was withdrawn from US market in 1977 on the basis of reports of agranulocytosis.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
Mode of analgesic action of dipyrone: direct antagonism of inflammatory hyperalgesia.	1985 Aug 27	2998815
Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships.	1987 Nov	3425858
Activation of the arginine-nitric oxide pathway in primary sensory neurons contributes to dipyrone-induced spinal and peripheral analgesia.	1996 Jun	8814464
Use of dipyrone during pregnancy and risk of Wilms' tumor. Brazilian Wilms' Tumor Study Group.	1996 Sep	8862987
Spinal and supraspinal antinociceptive action of dipyrone in formalin, capsaicin and glutamate tests. Study of the mechanism of action.	1998 Mar 26	9592021
Doctor, there's a fly in my soup! Angiotensin-converting enzyme inhibitors, endogenous opioids and visual hallucinations.	2001 Dec	11794927
Allergic cholestatic hepatitis and exanthema induced by metamizole: verification by lymphocyte transformation test.	2002 Dec	12445177
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.	2002 Jan	11852909
[Postoperative analgesia with tramadol and metamizol. Continual infusion versus patient controlled analgesia].	2003 Jan	12577163
[Multifocal brain haemorrhage associated with migraine and medication abuse].	2003 Nov 1-15	14606052
Antinociceptive profile of (-)-spectaline: a piperidine alkaloid from Cassia leptophylla.	2003 Sep	14598202
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

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

Common Name

English

Metamizole [WHO-DD]

Common Name

English

METHAMIZOLE-

Common Name

English

METHANESULFONIC ACID, (ANTIPYRINYLMETHYLAMINO)-

Common Name

English

METHANESULFONIC ACID, ((2,3-DIHYDRO-1,5-DIMETHYL-3-OXO-2-PHENYL-1H-PYRAZOL-4-YL)METHYLAMINO)-

Common Name

English

Dipyrone free acid anhydrous

Common Name

English

METHANESULFONIC ACID, 1-((2,3-DIHYDRO-1,5-DIMETHYL-3-OXO-2-PHENYL-1H-PYRAZOL-4-YL)METHYLAMINO)-

Common Name

English

Classification Tree Code System Code

WHO-ATC

N02BB72