Introduction：Basic information about CAS 68-89-3|Metamizole sodium, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Metamizole sodium |
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| CAS Number | 68-89-3 | Molecular Weight | 333.339 |
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| Density | / | Boiling Point | / |
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| Molecular Formula | C13H16N3NaO4S | Melting Point | 187ºC |
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| MSDS | / | Flash Point | / |
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Names
| Name | metamizole sodium |
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| Synonym | More Synonyms |
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Metamizole sodium BiologicalActivity
| Description | Metamizole sodium is a non-opioid compound with excellent analgesic and antipyretic effects. Metamizole (sodium) is a cyclooxygenase-3 (COX-3) inhibitor[1][2]. |
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| Related Catalog | Research Areas >>Inflammation/ImmunologySignaling Pathways >>Immunology/Inflammation >>COXResearch Areas >>Neurological Disease |
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| Target | COX-3[2] |
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| In Vitro | Metamizole sodium inhibits COX-3 with IC50 value of 52 μM and COX-1 at a 6.6-fold higher concentration in insect cells[2]. Metamizole (1-500 μM; 48 hours) significantly inhibits cell proliferation in pancreatic cancer cells[3]. Cell Proliferation Assay[3] Cell Line: Pancreatic cancer cell lines PaTu 8988t and Panc-1 Concentration: 1 μM, 10 μM, 100 μM, 250 μM, 500 μM Incubation Time: 48 hours Result: Significantly inhibited cell proliferation in the PaTu 8988t cell line; significantly inhibited cell proliferation in the pancreatic cancer cell line Panc-1 at 1-250 μM. |
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| In Vivo | Metamizole sodium (500 mg/kg; i.p.; twice a day; for 7 days) diminishes the development of neuropathic pain symptoms in rats[4]. Animal Model: Male Wistar rats (270-300 g), with peripheral neuropathic pain[4] Dosage: 500 mg/kg Administration: Intraperitoneal injection, twice a day, for 7 days Result: Diminished the expression of pronociceptive interleukins (IL-1beta, IL-6, and IL-18) and chemokines (CCL2, CCL4, and CCL7) in DRG measured 7 days after sciatic nerve injury. |
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| References | [1]. A Jasiecka, et al. Pharmacological characteristics of metamizole. Pol J Vet Sci. 2014;17(1):207-14. [2]. N V Chandrasekharan, et al. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15; 99(21): 13926–13931. [3]. Manuela Malsy, et al. Effects of metamizole, MAA, and paracetamol on proliferation, apoptosis, and necrosis in the pancreatic cancer cell lines PaTu 8988 t and Panc-1. BMC Pharmacol Toxicol. 2017 Dec 6;18(1):77. [4]. Renata Zajaczkowska, et al. Metamizole relieves pain by influencing cytokine levels in dorsal root ganglia in a rat model of neuropathic pain. Pharmacol Rep. 2020 Oct;72(5):1310-1322. |
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Chemical & Physical Properties
| Melting Point | 187ºC |
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| Molecular Formula | C13H16N3NaO4S |
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| Molecular Weight | 333.339 |
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| Exact Mass | 333.075928 |
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| PSA | 95.75000 |
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| LogP | 1.50410 |
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| InChIKey | DJGAAPFSPWAYTJ-UHFFFAOYSA-M |
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| SMILES | Cc1c(N(C)CS(=O)(=O)[O-])c(=O)n(-c2ccccc2)n1C.[Na+] |
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| Stability | Stable. Incompatible with strong oxidizing agents. |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- PB1300000
- CHEMICAL NAME :
- Methanesulfonic acid, (antipyrinylmethylamino)-, monosodium salt
- CAS REGISTRY NUMBER :
- 68-89-3
- LAST UPDATED :
- 199607
- DATA ITEMS CITED :
- 37
- MOLECULAR FORMULA :
- C13-H17-N3-O4-S.Na
- MOLECULAR WEIGHT :
- 334.38
- WISWESSER LINE NOTATION :
- T5NNVJ A1 BR& D1M1SWQ E1
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3 gm/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
- TYPE OF TEST :
- LC - Lethal concentration
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >900 mg/m3
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2470 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2117 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2182 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intramuscular
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1625 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2891 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LC50 - Lethal concentration, 50 percent kill
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 37200 mg/m3
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 250 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 69 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2197 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2750 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 2150 mg/kg
- TOXIC EFFECTS :
- Behavioral - changes in motor activity (specific assay) Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - respiratory stimulation
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 3 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - guinea pig
- DOSE/DURATION :
- 3 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 61800 mg/kg/30D-I
- TOXIC EFFECTS :
- Endocrine - changes in spleen weight Blood - pigmented or nucleated red blood cells Blood - changes in leukocyte (WBC) count
- TYPE OF TEST :
- TCLo - Lowest published toxic concentration
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 192 mg/m3/4H/30D-I
- TOXIC EFFECTS :
- Behavioral - alteration of classical conditioning Liver - liver function tests impaired
- TYPE OF TEST :
- TCLo - Lowest published toxic concentration
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 20 mg/m3/4H/17W-I
- TOXIC EFFECTS :
- Brain and Coverings - recordings from specific areas of CNS Blood - change in clotting factors Nutritional and Gross Metabolic - other changes
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 45500 mg/kg/13W-C
- TOXIC EFFECTS :
- Liver - other changes Kidney, Ureter, Bladder - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 60 gm/kg/30D-C
- TOXIC EFFECTS :
- Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intramuscular
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 60 gm/kg/30D-C
- TOXIC EFFECTS :
- Blood - normocytic anemia Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 6300 mg/kg/30D-I
- TOXIC EFFECTS :
- Endocrine - other changes Blood - changes in other cell count (unspecified)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 536 mg/kg/78W-C
- TOXIC EFFECTS :
- Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Liver - tumors
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 792 mg/kg/78W-C
- TOXIC EFFECTS :
- Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Liver - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 30 mg/kg
- SEX/DURATION :
- lactating female 41 day(s) post-birth
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - other neonatal measures or effects
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 750 mg/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - Central Nervous System
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 1 gm/kg
- SEX/DURATION :
- female 9 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- Mutation test systems - not otherwise specified
- TYPE OF TEST :
- Cytogenetic analysis
- TYPE OF TEST :
- Cytogenetic analysis
MUTATION DATA - TYPE OF TEST :
- Cytogenetic analysis
- TEST SYSTEM :
- Rodent - hamster Fibroblast
- DOSE/DURATION :
- 750 mg/L
- REFERENCE :
- ESKHA5 Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. (Kokuritsu Eisei Shikenjo Kagaku, 18-1 Bushitsu Johobu, Setagaya-ku, Tokyo 158, Japan) V.1- 1886- Volume(issue)/page/year: (96),55,1978 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.5 mg/m3 JAN 1993
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Safety Information
| Hazard Codes | Xn:Harmful; |
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| Risk Phrases | R42/43 |
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| Safety Phrases | S36 |
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| WGK Germany | 2 |
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| RTECS | PB1300000 |
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| HS Code | 2933192000 |
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Customs
Synonyms
| narone |
| Novil |
| Magnopyrol |
| Methamizole Sodium |
| Sodium [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulfonate |
| pyrojec |
| conmel |
| Novacid |
| Sulpin |
| Sodium [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonate |
| Sodium 1-Phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethanesulfonate |
| Unagen |
| fevonil |
| barone |
| Dipyron |
| Nartate |
| Anador |
| pyretin |
| ARPF |
| Methanesulfonic acid, 1-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]-, sodium salt (1:1) |
| EINECS 200-694-7 |
| Alangin |
| MFCD00020783 |
