Dipyrone | CAS# 68-89-3 | anti-inflammatory

MedKoo Cat#: 592898 | Name: Dipyrone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dipyrone (metamizole) is a non-opioid analgesic and antipyretic drug that inhibits cyclooxygenase (COX) enzymes, reducing prostaglandin synthesis and thereby alleviating pain and fever. It also has spasmolytic properties, likely due to calcium channel modulation and nitric oxide release. Despite its effectiveness, dipyrone is banned in some countries due to the risk of agranulocytosis, a severe adverse effect affecting white blood cell production.

Chemical Structure

Dipyrone

CAS#68-89-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 592898

Name: Dipyrone

CAS#: 68-89-3 (sodium)

Chemical Formula: C13H16N3NaO4S

Exact Mass: 0.0000

Molecular Weight: 333.34

Elemental Analysis: C, 46.84; H, 4.84; N, 12.61; Na, 6.90; O, 19.20; S, 9.62

Price and Availability

Size	Price	Availability	Quantity
25g	USD 400.00	2 Weeks
50g	USD 550.00	2 Weeks

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Related CAS #

50567-35-6 (free acid) 68-89-3 (sodium) 5907-38-0 (sodium hydrate) 6150-97-6 (magnesium)

Synonym

Dipyrone; Sulpin; Sulpyrin; Sulpyrine; Analgin; Metamizole sodium; Novalgin

IUPAC/Chemical Name

sodium ((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino)methanesulfonate

InChi Key

DJGAAPFSPWAYTJ-UHFFFAOYSA-M

InChi Code

InChI=1S/C13H17N3O4S.Na/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);/q;+1/p-1

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Metamizole (sodium) is a cyclooxygenase-3 (COX-3) inhibitor.

In vitro activity:

In the pancreatic cancer cell line Panc-1, proliferation was significantly inhibited with concentrations of 1 μM, 10 μM, 100 μM, and 250 μM of metamizole (Fig. 1a). Reference: BMC Pharmacol Toxicol. 2017 Dec 6;18(1):77. https://pubmed.ncbi.nlm.nih.gov/29208039/

In vivo activity:

These behavioral results provide evidence that repeated intraperitoneal administration of metamizole diminishes the development of neuropathic pain symptoms in rats. Simultaneously, these findings provide evidence that metamizole diminishes 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. These assays indicate, for the first time, that metamizole exerts antinociceptive effects on nerve injury-induced neuropathic pain at the DRG level. Reference: Pharmacol Rep. 2020 Oct;72(5):1310-1322. https://pubmed.ncbi.nlm.nih.gov/32691345/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	90.00
	DMSO	30.0	90.00
	Ethanol	20.0	60.00
	PBS (pH 7.2)	10.0	30.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 333.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cecílio NT, Souza GR, Alves-Filho JC, Cunha FQ, Cunha TM. The PI3Kγ/AKT signaling pathway mediates peripheral antinociceptive action of dipyrone. Fundam Clin Pharmacol. 2021 Apr;35(2):364-370. doi: 10.1111/fcp.12606. Epub 2020 Oct 10. PMID: 32979233. 2. Malsy M, Graf B, Bundscherer A. 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. doi: 10.1186/s40360-017-0185-y. PMID: 29208039; PMCID: PMC5717838. 3. Passoni MT, Krebs Ribeiro DC, França de Almeida SC, Furtado da Costa B, Grechi N, Lima Tolouei SE, Curi TZ, Degraf Cavallin M, Romano RM, Romano MA, Spercoski KM, Carvalho Dos Santos A, Carvalho Souza RI, Dalsenter PR, Martino-Andrade AJ. The Analgesic Dipyrone Affects Pregnancy Outcomes and Endocrine-Sensitive Endpoints in Female and Male Offspring Rats. Toxicol Sci. 2022 Apr 26;187(1):80-92. doi: 10.1093/toxsci/kfac016. PMID: 35171999. 4. Zajaczkowska R, Kwiatkowski K, Pawlik K, Piotrowska A, Rojewska E, Makuch W, Wordliczek J, Mika J. 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. doi: 10.1007/s43440-020-00137-8. Epub 2020 Jul 20. PMID: 32691345; PMCID: PMC7550285.

In vitro protocol:

In vivo protocol:

1. Passoni MT, Krebs Ribeiro DC, França de Almeida SC, Furtado da Costa B, Grechi N, Lima Tolouei SE, Curi TZ, Degraf Cavallin M, Romano RM, Romano MA, Spercoski KM, Carvalho Dos Santos A, Carvalho Souza RI, Dalsenter PR, Martino-Andrade AJ. The Analgesic Dipyrone Affects Pregnancy Outcomes and Endocrine-Sensitive Endpoints in Female and Male Offspring Rats. Toxicol Sci. 2022 Apr 26;187(1):80-92. doi: 10.1093/toxsci/kfac016. PMID: 35171999. 2. Zajaczkowska R, Kwiatkowski K, Pawlik K, Piotrowska A, Rojewska E, Makuch W, Wordliczek J, Mika J. 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. doi: 10.1007/s43440-020-00137-8. Epub 2020 Jul 20. PMID: 32691345; PMCID: PMC7550285.

1: Polzin A, Richter S, Schrör K, Rassaf T, Merx MW, Kelm M, Hohlfeld T, Zeus T. Prevention of dipyrone (metamizole) induced inhibition of aspirin antiplatelet effects. Thromb Haemost. 2015 Jul;114(1):87-95. doi: 10.1160/TH14-11-0922. Epub 2015 Mar 19. PubMed PMID: 25789542. 2: Crunfli F, Vilela FC, Giusti-Paiva A. Cannabinoid CB1 receptors mediate the effects of dipyrone. Clin Exp Pharmacol Physiol. 2015 Mar;42(3):246-55. doi: 10.1111/1440-1681.12347. PubMed PMID: 25430877. 3: Lampl C, Likar R. [Metamizole (dipyrone): mode of action, drug-drug interactions, and risk of agranulocytosis]. Schmerz. 2014 Dec;28(6):584-90. doi: 10.1007/s00482-014-1490-7. Review. German. PubMed PMID: 25199942. 4: Zanuzzo FS, Teixeira-Neto FJ, Thomazini CM, Takahira RK, Conner B, Diniz MS. Effects of dipyrone, meloxicam, or the combination on hemostasis in conscious dogs. J Vet Emerg Crit Care (San Antonio). 2015 Jul-Aug;25(4):512-20. doi: 10.1111/vec.12336. Epub 2015 Jun 25. PubMed PMID: 26112345. 5: Zapater P, Llanos L, Barquero C, Bellot P, Pascual S, Carnicer F, Palazón JM, Gimenez P, Esteban A, Llorca L, Francés R, Horga JF, Such J. Acute effects of dipyrone on renal function in patients with cirrhosis: a randomized controlled trial. Basic Clin Pharmacol Toxicol. 2015 Mar;116(3):257-63. doi: 10.1111/bcpt.12312. Epub 2014 Oct 8. PubMed PMID: 25154757. 6: Malvar Ddo C, Aguiar FA, Vaz Ade L, Assis DC, de Melo MC, Jabor VA, Kalapothakis E, Ferreira SH, Clososki GC, de Souza GE. Dipyrone metabolite 4-MAA induces hypothermia and inhibits PGE2 -dependent and -independent fever while 4-AA only blocks PGE2 -dependent fever. Br J Pharmacol. 2014 Aug;171(15):3666-79. doi: 10.1111/bph.12717. PubMed PMID: 24712707; PubMed Central PMCID: PMC4128064. 7: Ramacciotti AS, Soares BG, Atallah AN. WITHDRAWN: Dipyrone for acute primary headaches. Cochrane Database Syst Rev. 2014 Jul 11;(7):CD004842. doi: 10.1002/14651858.CD004842.pub3. Review. PubMed PMID: 25019294. 8: Moore RA, Derry S, Wiffen PJ, Straube S. Effects of food on pharmacokinetics of immediate release oral formulations of aspirin, dipyrone, paracetamol and NSAIDs - a systematic review. Br J Clin Pharmacol. 2015 Sep;80(3):381-8. doi: 10.1111/bcp.12628. Epub 2015 Jul 6. Review. PubMed PMID: 25784216; PubMed Central PMCID: PMC4574824. 9: Ertin IH, Gunduz O, Ulugol A. Contribution of nociceptin/orphanin FQ receptors to the anti-nociceptive and hypothermic effects of dipyrone. Acta Neuropsychiatr. 2015 Feb;27(1):48-52. doi: 10.1017/neu.2014.38. Epub 2014 Dec 3. PubMed PMID: 25467825. 10: Nassini R, Fusi C, Materazzi S, Coppi E, Tuccinardi T, Marone IM, De Logu F, Preti D, Tonello R, Chiarugi A, Patacchini R, Geppetti P, Benemei S. The TRPA1 channel mediates the analgesic action of dipyrone and pyrazolone derivatives. Br J Pharmacol. 2015 Jul;172(13):3397-411. doi: 10.1111/bph.13129. Epub 2015 Apr 24. PubMed PMID: 25765567; PubMed Central PMCID: PMC4500374. 11: Gencer A, Gunduz O, Ulugol A. Involvement of Descending Serotonergic and Noradrenergic Systems and their Spinal Receptor Subtypes in the Antinociceptive Effect of Dipyrone. Drug Res (Stuttg). 2015 Dec;65(12):645-9. doi: 10.1055/s-0034-1398550. Epub 2015 Feb 3. PubMed PMID: 25647230. 12: Hoffmann F, Meinecke P, Freitag MH, Glaeske G, Schulze J, Schmiemann G. Who gets dipyrone (metamizole) in Germany? Prescribing by age, sex and region. J Clin Pharm Ther. 2015 Jun;40(3):285-8. doi: 10.1111/jcpt.12261. Epub 2015 Mar 16. PubMed PMID: 25776531. 13: Maione S, Radanova L, De Gregorio D, Luongo L, De Petrocellis L, Di Marzo V, Imming P. Effects of metabolites of the analgesic agent dipyrone (metamizol) on rostral ventromedial medulla cell activity in mice. Eur J Pharmacol. 2015 Feb 5;748:115-22. doi: 10.1016/j.ejphar.2014.12.022. Epub 2014 Dec 31. PubMed PMID: 25557763. 14: Dannenberg L, Erschoff V, Bönner F, Gliem M, Jander S, Levkau B, Kelm M, Hohlfeld T, Zeus T, Polzin A. Dipyrone comedication in aspirin treated stroke patients impairs outcome. Vascul Pharmacol. 2016 Dec;87:66-69. doi: 10.1016/j.vph.2016.06.003. Epub 2016 Jun 11. PubMed PMID: 27301652. 15: Edwards J, Meseguer F, Faura C, Moore RA, McQuay HJ, Derry S. Single dose dipyrone for acute postoperative pain. Cochrane Database Syst Rev. 2010 Sep 8;(9):CD003227. doi: 10.1002/14651858.CD003227.pub2. Review. Update in: Cochrane Database Syst Rev. 2013;11:CD003227. PubMed PMID: 20824835; PubMed Central PMCID: PMC4160844. 16: Aguiar FA, Malvar Ddo C, Vaz Ade L, Calixto LA, Clososki GC, de Gaitani CM, de Souza GE, Jabor VA. Simultaneous determination of dipyrone metabolites in rat hypothalamus, cerebrospinal fluid and plasma samples by LC-MS/MS. Bioanalysis. 2013 Nov;5(21):2631-45. doi: 10.4155/bio.13.229. PubMed PMID: 24180504. 17: Gyenge-Szabó Z, Szoboszlai N, Frigyes D, Záray G, Mihucz VG. Monitoring of four dipyrone metabolites in communal wastewater by solid phase extraction liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal. 2014 Mar;90:58-63. doi: 10.1016/j.jpba.2013.11.019. Epub 2013 Nov 24. PubMed PMID: 24333705. 18: Derry S, Faura C, Edwards J, McQuay HJ, Moore RA. WITHDRAWN: Single dose dipyrone for acute postoperative pain. Cochrane Database Syst Rev. 2013 Nov 25;(11):CD003227. doi: 10.1002/14651858.CD003227.pub3. Review. PubMed PMID: 24277663. 19: Elmas P, Ulugol A. Involvement of cannabinoid CB1 receptors in the antinociceptive effect of dipyrone. J Neural Transm (Vienna). 2013 Nov;120(11):1533-8. doi: 10.1007/s00702-013-1052-7. Epub 2013 Jun 20. PubMed PMID: 23784345. 20: Yıldırım E, Sağıroğlu O, Kılıç FS, Erol K. Effects of nabumetone and dipyrone on experimentally induced gastric ulcers in rats. Inflammation. 2013 Apr;36(2):476-81. doi: 10.1007/s10753-012-9568-9. PubMed PMID: 23129452.