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Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N3O4S.Na.H2O
Molecular Weight 351.354
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPYRONE

SMILES

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

InChI

InChIKey=UNZIDPIPYUMVPA-UHFFFAOYSA-M
InChI=1S/C13H17N3O4S.Na.H2O/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);;1H2/q;+1;/p-1

HIDE SMILES / InChI

Molecular Formula C13H17N3O4S
Molecular Weight 311.357
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 It was withdrawn from US market in 1977 on the basis of reports of agranulocytosis.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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P23219|||Q5T7T7
Gene ID: 5742.0
Gene Symbol: PTGS1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.85 μg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
69.05 mg × h/L
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.62 h
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
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
42.4%
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%
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%
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%
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

Doses

DosePopulationAdverse 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:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
5 g single, intravenous
Studied dose
Dose: 5 g
Route: intravenous
Route: single
Dose: 5 g
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [Inhibition 10 uM]
no
no
no
no
no
no
yes [Inhibition 10 uM]
yes
Drug as victim
PubMed

PubMed

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

Sample Use Guides

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
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 17:49:22 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:22 GMT 2025
Record UNII
6429L0L52Y
Record Status Validated (UNII)
Record Version
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Name Type Language
METAMIZOLE SODIUM MONOHYDRATE
WHO-DD  
Preferred Name English
DIPYRONE
MI   USAN  
USAN  
Official Name English
SODIUM (ANTIPYRINYLMETHYLAMINO)METHANESULPHONATE MONOHYDRATE
Common Name English
ANALGIN
Common Name English
NSC-758445
Code English
DIPYRONE [MI]
Common Name English
SULPYRINE HYDRATE
JAN  
Common Name English
DIPYRONE [USAN]
Common Name English
DIPYRONE MONOHYDRATE
Systematic Name English
Metamizole sodium monohydrate [WHO-DD]
Common Name English
METHANESULFONIC ACID, ((2,3-DIHYDRO-1,5-DIMETHYL-3-OXO-2-PHENYL-1H-PYRAZOL-4-YL)METHYLAMINO)-, SODIUM SALT, MONOHYDRATE
Common Name English
DIPROFARN
Brand Name English
NOVALGIN
Common Name English
METAMIZOL
Common Name English
METHAMPYRONE
Common Name English
METAMIZOLE SODIUM HYDRATE
Common Name English
NSC-73205
Code English
SULPYRINE
Brand Name English
SULPYRINE HYDRATE [JAN]
Common Name English
Sodium (antipyrinylmethylamino)methanesulfonate monohydrate
Common Name English
METAMIZOLE SODIUM MONOHYDRATE [EP MONOGRAPH]
Common Name English
NOVALDIN
Brand Name English
((2,3-DIHYDRO-1,5-DIMETHYL-3-OXO-2-PHENYL-1H-PYRAZOL-4-YL)METHYLAMINO)METHANESULFONIC ACID SODIUM SALT MONOHYDRATE
Common Name English
METAMIZOL MONOHYDRATE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
Code System Code Type Description
EVMPD
SUB03191MIG
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
ChEMBL
CHEMBL461522
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PRIMARY
EVMPD
SUB08810MIG
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
MERCK INDEX
m4660
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY Merck Index
CHEBI
59033
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
NCI_THESAURUS
C65435
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID10110043
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PRIMARY
CHEBI
62088
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PRIMARY
RXCUI
3523
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY RxNorm
EVMPD
SUB03187MIG
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
NSC
73205
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PRIMARY
NSC
758445
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PRIMARY
DAILYMED
6429L0L52Y
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
CAS
5907-38-0
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
MESH
D004177
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
LACTMED
Dipyrone
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
PUBCHEM
23674183
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
DRUG BANK
DBSALT002438
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
FDA UNII
6429L0L52Y
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
SMS_ID
100000085944
Created by admin on Mon Mar 31 17:49:22 GMT 2025 , Edited by admin on Mon Mar 31 17:49:22 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity E by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY