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
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
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 | HO |
Molecular Weight | 17.0073 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.un.org/esa/coordination/CL12.pdf
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 It was withdrawn from US market in 1977 on the basis of reports of agranulocytosis.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 |
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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 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NEURALGIN Approved UseSevere 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 UseOptalgin 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 |
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Drug utilization and morbidity statistics for the evaluation of drug safety in Sweden. | 1984 |
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Modifying potential of thirty-one chemicals on the short-term development of gamma-glutamyl transpeptidase-positive foci in diethylnitrosamine-initiated rat liver. | 1984 Oct |
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Mode of analgesic action of dipyrone: direct antagonism of inflammatory hyperalgesia. | 1985 Aug 27 |
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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 Oct 3 |
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Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships. | 1987 Nov |
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Octreotide dependency and headache: a case report. | 1994 Aug |
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Activation of the arginine-nitric oxide pathway in primary sensory neurons contributes to dipyrone-induced spinal and peripheral analgesia. | 1996 Jun |
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Use of dipyrone during pregnancy and risk of Wilms' tumor. Brazilian Wilms' Tumor Study Group. | 1996 Sep |
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Spinal and supraspinal antinociceptive action of dipyrone in formalin, capsaicin and glutamate tests. Study of the mechanism of action. | 1998 Mar 26 |
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Urticaria induced by meperidine allergy. | 2000 Mar |
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Allergic cholestatic hepatitis and exanthema induced by metamizole: verification by lymphocyte transformation test. | 2002 Dec |
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A comparative study of the antipyretic effects of indomethacin and dipyrone in rats. | 2002 Jan |
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COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. | 2002 Oct 15 |
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Metamizole intolerance and bronchial asthma. | 2002 Sep-Oct |
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[Postoperative analgesia with tramadol and metamizol. Continual infusion versus patient controlled analgesia]. | 2003 Jan |
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[Multifocal brain haemorrhage associated with migraine and medication abuse]. | 2003 Nov 1-15 |
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Antinociceptive profile of (-)-spectaline: a piperidine alkaloid from Cassia leptophylla. | 2003 Sep |
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Effects of celecoxib on acid-challenged gastric mucosa of rats: comparison with metamizol and piroxicam. | 2004 Jun |
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Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention. | 2005 Dec |
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[Acute intermittent porphyria and oral contraception. Case report]. | 2006 Mar |
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Over-expression of the LTC4 synthase gene in mice reproduces human aspirin-induced asthma. | 2011 Aug |
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Synergistic effect of the L-tryptophan and kynurenic acid with dipyrone or paracetamol in mice. | 2013 Sep 25 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12242329
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
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Edited
Fri Dec 15 15:11:07 GMT 2023
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Record UNII |
6429L0L52Y
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C257
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m4660
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59033
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D004177
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Dipyrone
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
correction factor: for the calculation of content, multiply the peak area of impurity E by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |