Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C13H16N3O4S.Mg |
Molecular Weight | 645.003 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Mg++].CN(CS([O-])(=O)=O)C1=C(C)N(C)N(C1=O)C2=CC=CC=C2.CN(CS([O-])(=O)=O)C3=C(C)N(C)N(C3=O)C4=CC=CC=C4
InChI
InChIKey=NHMUJYOBLYTIKO-UHFFFAOYSA-L
InChI=1S/2C13H17N3O4S.Mg/c2*1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11;/h2*4-8H,9H2,1-3H3,(H,18,19,20);/q;;+2/p-2
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 It was withdrawn from US market in 1977 on the basis of reports of agranulocytosis.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. |
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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 |
|
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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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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[Effects of verapamil on behavioral and microcirculatory disorders in pain syndrome of spinal etiology]. | 1990 May |
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Octreotide dependency and headache: a case report. | 1994 Aug |
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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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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 |
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Urticaria induced by meperidine allergy. | 2000 Mar |
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Doctor, there's a fly in my soup! Angiotensin-converting enzyme inhibitors, endogenous opioids and visual hallucinations. | 2001 Dec |
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Metamizol potentiates morphine antinociception but not constipation after chronic treatment. | 2002 Apr 26 |
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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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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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Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS). | 2009 Jun |
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.
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ACTIVE MOIETY
SUBSTANCE RECORD