Sulfamerazine | CAS#127-79-7

MedKoo Cat#: 326825 | Name: Sulfamerazine

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Description:

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

Sulfamerazine is a long-acting sulfanilamide antibacterial agent. Sulfamerazine inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for the binding site on dihydropteroate synthase.

Chemical Structure

Sulfamerazine

CAS#127-79-7

Theoretical Analysis

MedKoo Cat#: 326825

Name: Sulfamerazine

CAS#: 127-79-7

Chemical Formula: C11H12N4O2S

Exact Mass: 264.0681

Molecular Weight: 264.30

Elemental Analysis: C, 49.99; H, 4.58; N, 21.20; O, 12.11; S, 12.13

Price and Availability

Size	Price	Availability	Quantity
50g	USD 250.00
250g	USD 450.00
500g	USD 950.00

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Related CAS #

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Synonym

Sulfamerazine; Mebacid; Methylsulfadiazine; Sulfamerazine; Trimetox.

IUPAC/Chemical Name

4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulfonamide

InChi Key

QPPBRPIAZZHUNT-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

SMILES Code

O=S(C1=CC=C(N)C=C1)(NC2=NC=CC(C)=N2)=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

>2 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 264.30 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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Sulfamerazine: Understanding the Influence of Slip Planes in the Polymorphic Phase Transformation through X-Ray Crystallographic Studies and ab Initio Lattice Dynamics. Mol Pharm. 2015 Oct 5;12(10):3735-48. doi: 10.1021/acs.molpharmaceut.5b00504. Epub 2015 Sep 8. PubMed PMID: 26317333. 5: Aloisio C, de Oliveira AG, Longhi M. Solubility and release modulation effect of sulfamerazine ternary complexes with cyclodextrins and meglumine. J Pharm Biomed Anal. 2014 Nov;100:64-73. doi: 10.1016/j.jpba.2014.07.008. Epub 2014 Jul 30. PubMed PMID: 25129645. 6: Macfhionnghaile P, Hu Y, Gniado K, Curran S, Mcardle P, Erxleben A. Effects of ball-milling and cryomilling on sulfamerazine polymorphs: a quantitative study. J Pharm Sci. 2014 Jun;103(6):1766-78. doi: 10.1002/jps.23978. Epub 2014 Apr 22. PubMed PMID: 24756899. 7: Rajendiran N, Mohandoss T, Venkatesh G. Investigation of inclusion complexes of sulfamerazine with α- and β-cyclodextrins: an experimental and theoretical study. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:441-50. doi: 10.1016/j.saa.2014.01.057. Epub 2014 Jan 21. PubMed PMID: 24508883. 8: Lou H, Liu M, Qu W, Johnson J, Brunson E, Almoazen H. The influence of sodium salts (iodide, chloride and sulfate) on the formation efficiency of sulfamerazine nanocrystals. Pharm Dev Technol. 2014 Aug;19(5):548-55. doi: 10.3109/10837450.2013.805777. Epub 2013 Jun 13. PubMed PMID: 23763457. 9: Aloisio C, Gomes de Oliveira A, Longhi M. Characterization, inclusion mode, phase-solubility and in vitro release studies of inclusion binary complexes with cyclodextrins and meglumine using sulfamerazine as model drug. Drug Dev Ind Pharm. 2014 Jul;40(7):919-28. doi: 10.3109/03639045.2013.790408. Epub 2013 Apr 29. PubMed PMID: 23627444. 10: Lee MJ, Seo DY, Wang IC, Chun NH, Lee HE, Jeong MY, Kim WS, Choi GJ. Quantitative in-line monitoring of solvent-mediated polymorphic transformation of sulfamerazine by near-infrared spectroscopy. J Pharm Sci. 2012 Apr;101(4):1578-86. doi: 10.1002/jps.23042. Epub 2012 Jan 10. PubMed PMID: 22234855. 11: Kawakami K, Asami Y, Takenoshita I. Calorimetric investigation of solvent-mediated transformation of sulfamerazine polymorphism. J Pharm Sci. 2010 Jan;99(1):76-81. doi: 10.1002/jps.21837. PubMed PMID: 19718749. 12: Wang ZH, Zhang SX, Shen JZ. [Development of a fluorescence polarization immunoassay for sulfamerazine]. Guang Pu Xue Yu Guang Pu Fen Xi. 2008 Jul;28(7):1621-5. Chinese. PubMed PMID: 18844174. 13: Esrafili MD, Behzadi H, Beheshtian J, Hadipour NL. Theoretical 14N nuclear quadrupole resonance parameters for sulfa drugs: sulfamerazine and sulfathiazole. J Mol Graph Model. 2008 Oct;27(3):326-31. doi: 10.1016/j.jmgm.2008.05.007. Epub 2008 Jun 5. PubMed PMID: 18603459. 14: Guo L, Jiang X, Yang C, Zhang H. Analysis of sulfamerazine in pond water and several fishes by high-performance liquid chromatography using molecularly imprinted solid-phase extraction. Anal Bioanal Chem. 2008 Jul;391(6):2291-8. doi: 10.1007/s00216-008-2131-8. Epub 2008 May 22. PubMed PMID: 18496678. 15: Reguera C, Ortiz MC, Herrero A, Sarabia LA. Optimization of a FIA system with amperometric detection by means of a desirability function: determination of sulfadiazine, sulfamethazine and sulfamerazine in milk. Talanta. 2008 Mar 15;75(1):274-83. doi: 10.1016/j.talanta.2007.11.030. Epub 2007 Nov 17. PubMed PMID: 18371879. 16: Gong Y, Collman BM, Mehrens SM, Lu E, Miller JM, Blackburn A, Grant DJ. Stable-form screening: overcoming trace impurities that inhibit solution-mediated phase transformation to the stable polymorph of sulfamerazine. J Pharm Sci. 2008 Jun;97(6):2130-44. PubMed PMID: 17879974. 17: Cao X, Sun C, Thamann TJ. A study of sulfamerazine single crystals using atomic force microscopy, transmission light microscopy, and Raman spectroscopy. J Pharm Sci. 2005 Sep;94(9):1881-92. PubMed PMID: 16052565. 18: Roy S, Alexander KS, Riga AT, Chatterjee K. Characterization of physical mixtures and directly compressed tablets of sulfamerazine polymorphs: implications on in vitro release characteristics. J Pharm Sci. 2003 Apr;92(4):747-59. PubMed PMID: 12661061. 19: Zhang GG, Gu C, Zell MT, Burkhardt RT, Munson EJ, Grant DJ. Crystallization and transitions of sulfamerazine polymorphs. J Pharm Sci. 2002 Apr;91(4):1089-100. PubMed PMID: 11948548. 20: Sun C, Grant DJ. Influence of crystal structure on the tableting properties of sulfamerazine polymorphs. Pharm Res. 2001 Mar;18(3):274-80. PubMed PMID: 11442264.