Synonym
HSDB 4157; HSDB 4157; HSDB 4157; Sulfamethazine; Intradine; Kelametazine
IUPAC/Chemical Name
5-((4-aminophenyl)sulfonyl)-4,6-dimethylpyrimidin-2-amine
InChi Key
XHSRRHQRYQKCGA-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H14N4O2S/c1-7-11(8(2)16-12(14)15-7)19(17,18)10-5-3-9(13)4-6-10/h3-6H,13H2,1-2H3,(H2,14,15,16)
SMILES Code
CC1=C(S(=O)(C2=CC=C(N)C=C2)=O)C(C)=NC(N)=N1
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, not in water
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
2935903000
Biological target:
Sulfamethazine (Sulfadimidine) is an antimicrobial that is widely used to treat and prevent various animal diseases (such as gastrointestinal and respiratory tract infections).
In vitro activity:
In this study, the SMZ (sulfamethazine)-degrading strain A01 belonging to the genus Paenarthrobacter was isolated from SMZ-enriched activated sludge reactors. The effects of pH, temperature, initial substrate concentration and additional carbon source on the biodegradation of SMZ were investigated. The results indicated that pH 6.0-7.8, 25 °C and the addition of 0.2 g/L sodium acetate favored the biodegradation, whereas a high concentration of SMZ, 500 mg/L, had an inhibitory effect. The biodegradation kinetics with SMZ as the sole carbon source or 0.2 g/L sodium acetate as the co-substrate fit the modified Gompertz model well with a correlation coefficient (R2) of 0.99. Three biodegradation pathways were proposed involving nine biodegradation products, among which C6H9N3O2S and C12H12N2 were two novel biodegradation products that have not been reported previously. Approximately 90.7% of SMZ was transformed to 2-amino-4, 6-dimethylpyrimidine. Furthermore, sad genes responsible for catabolizing sulfonamides were characterized in A01 with high similarities of 96.0%-100.0%.
Reference: Environ Int. 2019 Oct;131:104961. https://pubmed.ncbi.nlm.nih.gov/31330364/
In vivo activity:
In this study, the SMZ (sulfamethazine)-degrading strain A01 belonging to the genus Paenarthrobacter was isolated from SMZ-enriched activated sludge reactors. The effects of pH, temperature, initial substrate concentration and additional carbon source on the biodegradation of SMZ were investigated. The results indicated that pH 6.0-7.8, 25 °C and the addition of 0.2 g/L sodium acetate favored the biodegradation, whereas a high concentration of SMZ, 500 mg/L, had an inhibitory effect. The biodegradation kinetics with SMZ as the sole carbon source or 0.2 g/L sodium acetate as the co-substrate fit the modified Gompertz model well with a correlation coefficient (R2) of 0.99. Three biodegradation pathways were proposed involving nine biodegradation products, among which C6H9N3O2S and C12H12N2 were two novel biodegradation products that have not been reported previously. Approximately 90.7% of SMZ was transformed to 2-amino-4, 6-dimethylpyrimidine. Furthermore, sad genes responsible for catabolizing sulfonamides were characterized in A01 with high similarities of 96.0%-100.0%.
Reference: Environ Int. 2019 Oct;131:104961. https://pubmed.ncbi.nlm.nih.gov/31330364/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
78.0 |
280.24 |
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
278.33
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. Cao L, Zhang J, Zhao R, Deng Y, Liu J, Fu W, Lei Y, Zhang T, Li X, Li B. Genomic characterization, kinetics, and pathways of sulfamethazine biodegradation by Paenarthrobacter sp. A01. Environ Int. 2019 Oct;131:104961. doi: 10.1016/j.envint.2019.104961. Epub 2019 Jul 19. PMID: 31330364.
2. Siddiqui H, Haniffa HM, Jabeen A, -Rahman AU, Choudhary MI. Sulphamethazine derivatives as immunomodulating agents: New therapeutic strategies for inflammatory diseases. PLoS One. 2018 Dec 19;13(12):e0208933. doi: 10.1371/journal.pone.0208933. PMID: 30566465; PMCID: PMC6300282.
3. . Sedqyar M, Kandiel MM, Weng Q, Nagaoka K, Watanabe G, Taya K. Effects of sulfamethazine on induction of precocious puberty in Japanese quails (Coturnix japonica) assessed through monitoring the hormonal changes and gonadal development. J Reprod Dev. 2012;58(5):563-8. doi: 10.1262/jrd.2012-036. Epub 2012 Jun 29. PMID: 22785325.
4. VAN Poucke LSG, VAN Peteghem CH. Pharmacokinetics and Tissue Residues of Sulfathiazole and Sulfamethazine in Pigs. J Food Prot. 1994 Sep;57(9):796-801. doi: 10.4315/0362-028X-57.9.796. PMID: 31121795.
In vitro protocol:
1. Cao L, Zhang J, Zhao R, Deng Y, Liu J, Fu W, Lei Y, Zhang T, Li X, Li B. Genomic characterization, kinetics, and pathways of sulfamethazine biodegradation by Paenarthrobacter sp. A01. Environ Int. 2019 Oct;131:104961. doi: 10.1016/j.envint.2019.104961. Epub 2019 Jul 19. PMID: 31330364.
2. Siddiqui H, Haniffa HM, Jabeen A, -Rahman AU, Choudhary MI. Sulphamethazine derivatives as immunomodulating agents: New therapeutic strategies for inflammatory diseases. PLoS One. 2018 Dec 19;13(12):e0208933. doi: 10.1371/journal.pone.0208933. PMID: 30566465; PMCID: PMC6300282.
In vivo protocol:
1. Sedqyar M, Kandiel MM, Weng Q, Nagaoka K, Watanabe G, Taya K. Effects of sulfamethazine on induction of precocious puberty in Japanese quails (Coturnix japonica) assessed through monitoring the hormonal changes and gonadal development. J Reprod Dev. 2012;58(5):563-8. doi: 10.1262/jrd.2012-036. Epub 2012 Jun 29. PMID: 22785325.
2. VAN Poucke LSG, VAN Peteghem CH. Pharmacokinetics and Tissue Residues of Sulfathiazole and Sulfamethazine in Pigs. J Food Prot. 1994 Sep;57(9):796-801. doi: 10.4315/0362-028X-57.9.796. PMID: 31121795.
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