Metamizole | CAS#50567-35-6 | COX3 Inhibitor

MedKoo Cat#: 535107 | Name: Metamizole

Description:

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

Metamizole is a cyclooxygenase 3 (COX3) inhibitor, acting as a potent inductor of cytochrome P450 isoenzymes CYP2B6 and CYP3A4.

Chemical Structure

Metamizole

CAS#50567-35-6

Theoretical Analysis

MedKoo Cat#: 535107

Name: Metamizole

CAS#: 50567-35-6

Chemical Formula: C13H17N3O4S

Exact Mass: 311.0940

Molecular Weight: 311.36

Elemental Analysis: C, 50.15; H, 5.50; N, 13.50; O, 20.55; S, 10.30

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Metamizole

IUPAC/Chemical Name

[(1,5-Dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonic acid

InChi Key

LVWZTYCIRDMTEY-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H17N3O4S/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)

SMILES Code

O=S(CN(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)C)(O)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 311.36 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

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PMID: 27346584. 5: Blaser L, Hassna H, Hofmann S, Holbro A, Haschke M, Rätz Bravo A, Zeller A, Krähenbühl S, Taegtmeyer A. Leucopenia associated with metamizole: a case- control study. Swiss Med Wkly. 2017 May 24;147:w14438. doi: 10.4414/smw.2017.14438. PMID: 28634963. 6: Stamer UM, Gundert-Remy U, Biermann E, Erlenwein J, Meiβner W, Wirz S, Stammschulte T. Metamizol : Überlegungen zum Monitoring zur frühzeitigen Diagnose einer Agranulozytose [Dipyrone (metamizole) : Considerations on monitoring for early detection of agranulocytosis]. Schmerz. 2017 Feb;31(1):5-13. German. doi: 10.1007/s00482-016-0160-3. PMID: 27766404. 7: Gonnert FA, Meißner W. Kasuistik: Metamizol-induzierte Agranulozytose [Case Report - Metamizole-Induced Agranulocytosis]. Anasthesiol Intensivmed Notfallmed Schmerzther. 2018 May;53(5):388-394. German. doi: 10.1055/s-0043-115329. Epub 2018 May 17. PMID: 29772595. 8: Witschi L, Reist L, Stammschulte T, Erlenwein J, Becke K, Stamer U. Perioperative Anwendung von Metamizol und anderen Nichtopioidanalgetika bei Kindern : Ergebnisse einer Umfrage [Perioperative use of metamizole and other nonopioid analgesics in children : Results of a survey]. Anaesthesist. 2019 Mar;68(3):152-160. German. doi: 10.1007/s00101-018-0532-4. Epub 2019 Jan 24. PMID: 30680415. 9: Gaertner J, Stamer UM, Remi C, Voltz R, Bausewein C, Sabatowski R, Wirz S, Müller-Mundt G, Simon ST, Pralong A, Nauck F, Follmann M, Radbruch L, Meißner W. Metamizole/dipyrone for the relief of cancer pain: A systematic review and evidence-based recommendations for clinical practice. Palliat Med. 2017 Jan;31(1):26-34. doi: 10.1177/0269216316655746. Epub 2016 Jul 20. PMID: 27435604. 10: Hearn L, Derry S, Moore RA. Single dose dipyrone (metamizole) for acute postoperative pain in adults. Cochrane Database Syst Rev. 2016 Apr 20;4(4):CD011421. doi: 10.1002/14651858.CD011421.pub2. PMID: 27096578; PMCID: PMC6540653. 11: Ziesenitz VC, Erb TO, Trachsel D, van den Anker JN. Safety of dipyrone (metamizole) in children-What's the risk of agranulocytosis? Paediatr Anaesth. 2018 Feb;28(2):186-187. doi: 10.1111/pan.13312. PMID: 29345086. 12: Greenhouse I, Attia-Konyo S, Mouallem M. [ACUTE RENAL FAILURE INDUCED BY METAMIZOLE]. Harefuah. 2019 Nov;158(11):721-723. Hebrew. PMID: 31721514. 13: Güttler K. Metamizol [Metamizole]. Schmerz. 2015 Apr;29(2):227-8. German. doi: 10.1007/s00482-015-1520-0. PMID: 25801326. 14: Vuik FE, Koehestanie P, Herbers AH, Terhaar Sive Droste JS. Chronic use of metamizole: not so safe after all? Neth J Med. 2017 Mar;75(2):81-83. PMID: 28276328. 15: Pfrepper C, Deters S, Metze M, Siegemund R, Gockel I, Petros S. Metamizole inhibits arachidonic acid-induced platelet aggregation after surgery and impairs the effect of aspirin in hospitalized patients. Eur J Clin Pharmacol. 2019 Jun;75(6):777-784. doi: 10.1007/s00228-019-02646-9. Epub 2019 Feb 18. PMID: 30778625. 16: Shah RR. Metamizole (dipyrone)-induced agranulocytosis: Does the risk vary according to ethnicity? J Clin Pharm Ther. 2019 Feb;44(1):129-133. doi: 10.1111/jcpt.12768. Epub 2018 Oct 11. PMID: 30311250. 17: Stessel B, Boon M, Pelckmans C, Joosten EA, Ory JP, Wyckmans W, Evers S, van Kuijk SMJ, Van de Velde M, Buhre WFFA. Metamizole vs. ibuprofen at home after day case surgery: A double-blind randomised controlled noninferiority trial. Eur J Anaesthesiol. 2019 May;36(5):351-359. doi: 10.1097/EJA.0000000000000972. PMID: 30946703. 18: Skaistys A, Rätz Bravo AE, Leuppi-Taegtmeyer A, Zysset Y. Agranulozytose nach Metamizol-Reexposition und Cefepim-induzierte Enzephalopathie mit fatalem Ausgang [Fatal Outcome of Agranulocytosis after Re-Exposure to Metamizole and Cefepime-Induced Encephalopathy]. Praxis (Bern 1994). 2019 Aug;108(10):693-697. German. doi: 10.1024/1661-8157/a003275. PMID: 31387493. 19: Kaya B, Elçin Işılgan S, Serel S, Ergün H. Metamizole: an effective solution for vasospasm. J Plast Surg Hand Surg. 2016 Jun;50(3):151-5. doi: 10.3109/2000656X.2015.1137924. Epub 2016 Feb 6. PMID: 26854097. 20: Fernández García PL, Ibáñez Camacho MF, López Pérez E. Trombocitopenia grave y agranulocitosis por metamizol [Severe thrombocytopenia and agranulocytosis associated with metamizole]. Med Clin (Barc). 2016 Oct 21;147(8):e43-e44. Spanish. doi: 10.1016/j.medcli.2016.06.008. Epub 2016 Jul 20. PMID: 27450174.