METAMIZOLE SODIUM

Possibly Marketed Outside US

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

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C13H16N3O4S
Molecular Weight	310.349
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 It was withdrawn from US market in 1977 on the basis of reports of agranulocytosis.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 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.actavis.bg/nr/rdonlyres/27cd192d-b3cd-4e81-a7a3-fa80f56bf148/0/neuragin_eng.pdf	Primary		Approved 8583	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 8583	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.

C_max

Value	Dose	Analyte	Population
13.85 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4043141/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2753071/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2753071/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
69.05 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4043141/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
51.33 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4043141/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
2.62 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4043141/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4043141/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2753071/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2753071/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Analyte	Population
42.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4054207/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	NORAMIDOPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
52.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4054207/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	AMPYRONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
82.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4054207/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	4-FORMYLAMINOANTIPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
85.8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4054207/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:	4-ACETAMINOANTIPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 g 3 times / day multiple, oral Highest studied dose Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8739093/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8739093/	Sources: https://pubmed.ncbi.nlm.nih.gov/8739093/
5 g single, intravenous Studied dose Dose: 5 g Route: intravenous Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/17953792/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17953792/	Sources: https://pubmed.ncbi.nlm.nih.gov/17953792/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193 inducer 440	inhibitor 2507 substrate 1388 inducer 109

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2E1 1060 OATP1B1 1079 P-gp 1741 CYP19A1 429 CYP2C19 2057 CYP2A6 879 OATP1B3 961 CYP1A2 2153	CYP2C8 810 CYP1A2 1197 CYP2C19 1119 CYP2B6 776 CYP2E1 729 P-gp 2052	CYP2B6 669 CYP2C19 329 P-gp 301

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDg3ODk0In19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDg3ODk0In19	no [IC50 >10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	no [Inhibition 10 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/522325#section=Biological-Test-Results Page: 258.0	no
CYP2C19 2141	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17344806/	no
CYP2C9 2497	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17344806/	no
CYP2D6 2546	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17344806/	no
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17344806/	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/522325#section=Biological-Test-Results Page: 11.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4Nzg5NCJ9fQ==	yes [Inhibition 10 uM]
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17344806/	yes

Drug as victim

Target	Modality	Activity	Metabolite
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	major	N-methyl-4-aminoantipyrine 5
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	major	N-methyl-4-aminoantipyrine 5
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	major	N-methyl-4-aminoantipyrine 5
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	major	N-methyl-4-aminoantipyrine 5
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	minor	N-methyl-4-aminoantipyrine 5
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	no	N-methyl-4-aminoantipyrine 5
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	no	N-methyl-4-aminoantipyrine 5
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29746911/	no	N-methyl-4-aminoantipyrine 5
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/522325#section=Biological-Test-Results Page: 308 \| 322	no

PubMed

Title	Date	PubMed
Synergistic effect of the L-tryptophan and kynurenic acid with dipyrone or paracetamol in mice.	2013-09-25	23872152
Over-expression of the LTC4 synthase gene in mice reproduces human aspirin-induced asthma.	2011-08	21429049
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).	2009-06	19617648
[Acute intermittent porphyria and oral contraception. Case report].	2006-03	16871841
Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention.	2005-12	16141368
Effects of celecoxib on acid-challenged gastric mucosa of rats: comparison with metamizol and piroxicam.	2004-06	15309881
[Multifocal brain haemorrhage associated with migraine and medication abuse].	2003-11-08	14606052
Antinociceptive profile of (-)-spectaline: a piperidine alkaloid from Cassia leptophylla.	2003-09	14598202
[Postoperative analgesia with tramadol and metamizol. Continual infusion versus patient controlled analgesia].	2003-01	12577163
Allergic cholestatic hepatitis and exanthema induced by metamizole: verification by lymphocyte transformation test.	2002-12	12445177
Metamizole intolerance and bronchial asthma.	2002-10-25	12396961
COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression.	2002-10-15	12242329
Metamizol potentiates morphine antinociception but not constipation after chronic treatment.	2002-04-26	12063090
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.	2002-01	11852909
Doctor, there's a fly in my soup! Angiotensin-converting enzyme inhibitors, endogenous opioids and visual hallucinations.	2001-12	11794927
Urticaria induced by meperidine allergy.	2000-03	10753031
Modifying effects of a mixture of acetaminophen, aspirin, dipyrone and ethenzamide on a multiorgan initiation model and its carcinogenicity in male F344 rats.	1999-01-08	10077225
Spinal and supraspinal antinociceptive action of dipyrone in formalin, capsaicin and glutamate tests. Study of the mechanism of action.	1998-03-26	9592021
Use of dipyrone during pregnancy and risk of Wilms' tumor. Brazilian Wilms' Tumor Study Group.	1996-09	8862987
Activation of the arginine-nitric oxide pathway in primary sensory neurons contributes to dipyrone-induced spinal and peripheral analgesia.	1996-06	8814464
Octreotide dependency and headache: a case report.	1994-08	7954762
[Effects of verapamil on behavioral and microcirculatory disorders in pain syndrome of spinal etiology].	1990-05	2378946
Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships.	1987-11	3425858
Risks of agranulocytosis and aplastic anemia. A first report of their relation to drug use with special reference to analgesics. The International Agranulocytosis and Aplastic Anemia Study.	1986-10-03	3747087
Mode of analgesic action of dipyrone: direct antagonism of inflammatory hyperalgesia.	1985-08-27	2998815
Modifying potential of thirty-one chemicals on the short-term development of gamma-glutamyl transpeptidase-positive foci in diethylnitrosamine-initiated rat liver.	1984-10	6150874
Drug utilization and morbidity statistics for the evaluation of drug safety in Sweden.	1984	6430038

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:37:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:37:39 GMT 2025`
Record UNII	VSU62Z74ON
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METAMIZOLE SODIUM

Official Name

English

DIPYRONE ANHYDROUS

Preferred 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

Classification Tree Code System Code

WHO-ATC

N02BB52