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68-89-3

68-89-3 structure
68-89-3 structure
  • Name: Metamizole sodium
  • Chemical Name: metamizole sodium
  • CAS Number: 68-89-3
  • Molecular Formula: C13H16N3NaO4S
  • Molecular Weight: 333.339
  • Catalog: API Antipyretic analgesics Antipyretic and analgesic
  • Create Date: 2018-03-15 08:00:00
  • Modify Date: 2025-08-25 10:43:57
  • Metamizole sodium is a non-opioid compound with excellent analgesic and antipyretic effects. Metamizole (sodium) is a cyclooxygenase-3 (COX-3) inhibitor[1][2].
Name metamizole sodium
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
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].
Related Catalog
Target

COX-3[2]

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.
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.
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.
Melting Point 187ºC
Molecular Formula C13H16N3NaO4S
Molecular Weight 333.339
Exact Mass 333.075928
PSA 95.75000
LogP 1.50410
Stability Stable. Incompatible with strong oxidizing agents.

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 DATA

ACUTE 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
Hazard Codes Xn:Harmful;
Risk Phrases R42/43
Safety Phrases S36
WGK Germany 2
RTECS PB1300000
HS Code 2933192000
HS Code 2933192000
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