Sulfadoxine

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Sulfadoxine
Category Bioactive by-products
Catalog number BBF-04006
CAS 2447-57-6
Molecular Weight 310.33
Molecular Formula C12H14N4O4S
Purity >98%

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Description

Sulfadoxine is an ultra-long-lasting sulfonamide with an IC50 of 249 μg/ml for P. vivax. Sulfadoxine is an ultra-long-lasting sulfonamide previously used in combination with pyrimethamine to treat or prevent malaria. Due to high levels of resistance, its use is no longer recommended routinely.

Specification

Synonyms WR-4873; WR4873; WR 4873; Solfadossina; Sulforthomidine
Storage Store at -20°C
IUPAC Name 4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
Canonical SMILES COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
InChI InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
InChI Key PJSFRIWCGOHTNF-UHFFFAOYSA-N

Properties

Appearance White to Off-white Solid
Application Antimalarials
Boiling Point 522.8°C at 760 mmHg
Melting Point 197°C
Flash Point 270.0±32.9 °C
Density 1.441 g/cm3
Solubility Soluble in Water

Reference Reading

1.A method for amplicon deep sequencing of drug resistance genes in Plasmodium falciparum clinical isolates from India.
Rao PN1, Uplekar S1, Kayal S2, Mallick PK3, Bandyopadhyay N3, Kale S3, Singh OP3, Mohanty A4, Mohanty S5, Wassmer SC6, Carlton JM7. J Clin Microbiol. 2016 Mar 23. pii: JCM.00235-16. [Epub ahead of print]
A major challenge to global malaria control and elimination is early detection and containment of emerging drug resistance. Next-generation sequencing (NGS) methods provide the resolution, scalability and sensitivity required for high-throughput surveillance of molecular markers of drug resistance. We have developed an amplicon sequencing method on the Ion Torrent PGM platform for targeted re-sequencing of a panel of sixPlasmodium falciparumgenes implicated in resistance to first-line antimalarial therapy, including artemisinin combination therapy, chloroquine, and sulfadoxine-pyrimethamine. The protocol was optimized using 12 geographically diverseP. falciparumreference strains, and successfully applied to multiplexed sequencing of 16 clinical isolates from India. Sequencing results from reference strains showed 100% concordance with previously reported drug resistance mutations. Single nucleotide polymorphisms (SNPs) in clinical isolates revealed a number of known resistance-associated mutations as well as other non-synonymous mutations that have not been implicated in drug resistance.
2.Assessment of the usage and effectiveness of intermittent preventive treatment and insecticide-treated nets on the indicators of malaria among pregnant women attending antenatal care in the Buea Health District, Cameroon.
Fokam EB1, Ngimuh L2, Anchang-Kimbi JK1, Wanji S3,4. Malar J. 2016 Mar 17;15(1):172. doi: 10.1186/s12936-016-1228-3.
BACKGROUND: Malaria in pregnancy is an immense public health problem with at least 50 million pregnant women living in malaria endemic areas. To prevent malaria and its complications in pregnancy the World Health Organization recommends the use of intermittent preventive treatment sulfadoxine-pyrimethamine (IPTp-SP), the use of insecticide-treated nets (ITNs), and effective case management. In most malaria endemic countries in Africa, 40 % of pregnant women sleep under ITNs. In Cameroon, about 90 % of pregnant women receive the first dose of SP, while 64 % take the complete dose. Following the 2011 mass-campaign of free distribution of ITNs coupled with routine ANC distribution of ITN and adoption of IPTp in Cameroon, little has been done to assess the effectiveness of both interventions outside of Yaoundé, the capital city. This study sought to assess the usage and effectiveness of IPTp-SP and ITNs on malaria in pregnancy.
3.MOLECULAR SURVEILLANCE OF Plasmodium vivax AND Plasmodium falciparum DHFR MUTATIONS IN ISOLATES FROM SOUTHERN IRAN.
Sharifi-Sarasiabi K1, Haghighi A2, Kazemi B3, Taghipour N2, Nazemalhosseini Mojarad E3, Gachkar L4. Rev Inst Med Trop Sao Paulo. 2016;58:e16. doi: 10.1590/S1678-9946201658016. Epub 2016 Mar 22.
In Iran, both Plasmodium vivax and P. falciparum malaria have been detected, but P. vivax is the predominant species. Point mutations in dihydrofolate reductase (dhfr) gene in both Plasmodia are the major mechanisms of pyrimethamine resistance. From April 2007 to June 2009, a total of 134 blood samples in two endemic areas of southern Iran were collected from patients infected with P. vivax and P. falciparum. The isolates were analyzed for P. vivax dihydrofolate reductase (pvdhfr) and P. falciparum dihydrofolate reductase (pfdhfr) point mutations using various PCR-based methods. The majority of the isolates (72.9%) had wild type amino acids at five codons of pvdhfr. Amongst mutant isolates, the most common pvdhfr alleles were double mutant in 58 and 117 amino acids (58R-117N). Triple mutation in 57, 58, and 117 amino acids (57L/58R/117N) was identified for the first time in the pvdhfr gene of Iranian P. vivax isolates. All the P. falciparumsamples analyzed (n = 16) possessed a double mutant pfdhfrallele (59R/108N) and retained a wild-type mutation at position 51.
4.Use of thin-layer chromatography to detect counterfeit sulfadoxine/pyrimethamine tablets with the wrong active ingredient in Malawi.
Khuluza F1, Kigera S2, Jähnke RW3, Heide L4,5. Malar J. 2016 Apr 14;15(1):215. doi: 10.1186/s12936-016-1259-9.
BACKGROUND: Substandard and falsified anti-malarial medicines pose a serious threat to public health, especially in low-income countries. Appropriate technologies for drug quality analysis in resource-limited settings are important for the surveillance of the formal and informal drug market. The feasibility of thin-layer chromatography (TLC) with different solvent systems was tested using the GPHF Minilab in a study of the quality of sulfadoxine/pyrimethamine tablets in Malawi.

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