Sulfad

 

Sulfadiazine, N1-2-pyrimidinylsulfanilamide (33.1.7), is synthesized by reacting 4-acetylaminobenzenesulfonyl chloride with 2-aminopyrimidine, which gives an acetanilide derivative (33.1.6). The subsequent hydrolysis of this product with a base leads to the formation of the desired sulfadiazine [5–8].


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Like sulfacytine, this drug is effective for infections caused by streptococci, gonococci, pneumococci, staphylococci as well as colon bacillus. Sulfadiazine is used for pneumonia, cerebral meningitis, staphylococcal and streptococcal sepsis, and other infectious diseases, although it is the drug of choice Sulfad nocardiosis. This drug is not recommended for urinary tract infections because of its low solubility and certain nephrotoxicity. Synonyms of this drug are flammazine, sterinor, terfonil, and others.

It is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action.


Six-membered Rings with Three or more Heteroatoms, and their Fused Carbocyclic Derivatives

G.W. Morrow, in Comprehensive Heterocyclic Chemistry III, 2008


9.06.1 Introduction

1-Oxa-2,5-diazines and 1-thia-2,5-diazines 1–4 and their benzo analogs 5 and 6 remain relatively obscure heterocyclic systems. While 1-oxa-2,5-diazinanes 1 and 5,6-dihydro-4H-1-oxa-2,5-diazines 2 continue to appear in recent studies, 4H-1-oxa-2,5-diazines 3 remain unknown. Several examples of the previously elusive 6H-1-oxa-2,5-diazine system 4 as well as a number of synthetic studies leading to 1-H-benzo-1-thia-2,5-diazines 6 have now been reported (Figure 1) and will be examined in this chapter. Additional information on these systems is available in Chapter 6.15 in CHEC-II(1996) <1995CHEC-II(6)681>, though the corresponding section in CHEC(1984) contains limited information on the 1-oxa-2,5-diazines and none on 1-thia-2,5-diazines <1984CHEC(3)1039>.



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Figure 1.


Fused Five- and Six-membered Rings without Ring Junction Heteroatoms

Stephen P. Stanforth, in Comprehensive Heterocyclic Chemistry II, 1996


7.15.10.1.2 Intramolecular reactions

Diazine (399) undergoes an intramolecular Diels–Alder reaction (195 °C, 135 h) yielding the intermediate (400) which fragments giving a mixture of the isomeric pyranopyridines (401) (40% yield) and (402) (22% yield) (Scheme 8) 〈89T6211〉. In the presence of TFA this reaction proceeds at 72 °C and gives heterocycle (402) (85% yield) 〈89T6519〉.



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Scheme 8.


Triazine (403) gives the naphthyridone derivative (404) (95% yield) in diphenyl ether under reflux 〈90CZ381〉. Triazines (405; R1, R2 = alkyl, aryl) give tetrahydropyranopyridines (406) in good yield at 200 °C 〈87T5145〉 and triazine (407) gives heterocycle (408) (30% yield) when heated in diphenyl ether 〈92AP(325)349〉. When triazine (409) is heated (64 h) in bromobenzene at reflux, the thiopyranopyridine derivative (410) (57% yield) is obtained 〈89JOC4984〉. The sulfone derivative (411) gives an excellent yield (99%) of the corresponding product (412) after 12 h at reflux in bromobenzene but, in contrast, the sulfoxide (413) gives only a trace of product (414). Salt (415) gives the tetrahydrothiopyranopyridine derivative (416) (40% yield) in dioxane at reflux 〈89T6499〉.



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Toxoplasmosis

J.K. Frenkel, in Encyclopedia of the Neurological Sciences, 2003


Treatment

The combination of sulfadiazine and pyrimethamine is the classic and probably best means of treating active disease; folinic acid can be added to avoid hematological toxicity without impairing the chemotherapeutic effect. Atovaquone may be added to inhibit another metabolic path of the organism. Treatment of pregnant women is complicated by drug toxicity to the more sensitive fetus. Clindamycin is sometimes substituted in the presense of hypersensitivity for one of the drugs mentioned, but it does not penetrate well into the central nervous system. When only co-trimoxazole is available, this is usually adequate. Also experimentally effective were arprinocid, trimetrexate, rifabutin, epiromin, and didanosine, and newer drugs are constantly being tested. For the best current drug combination and doses, a competent recent review or text should be consulted.


Toxoplasmosis☆

K.J. Baldwin, in Reference Module in Neuroscience and Biobehavioral Psychology, 2017


Treatment

The combination of sulfadiazine and pyrimethamine is probably the best means of treating active disease; folinic acid can be added to avoid hematological toxicity without impairing the chemotherapeutic effect. HIV patients with a CD4 count o200 should receive TMP/SMX prophylaxis to prevent reactivation of T. gondii. Atovaquone may be added to inhibit another metabolic path of the organism. Treatment of pregnant women is complicated by drug toxicity to the more sensitive fetus. If infection is confirmed in the first 18 weeks of pregnancy, treatment with spiramycin is recommended to prevent vertical transmission. Spiramycin does not cross the placenta and is not recommended for treating fetal infection. If fetal infection is confirmed by PCR of amniotic fluid or by ultrasound, therapy with pyrimethamine, sulfadiazine, and folinic acid is recommended. Clindamycin is sometimes substituted in the presence of hypersensitivity for one of the drugs mentioned, but it does not penetrate well into the CNS. For the best current drug combination and doses, a competent recent review or infectious disease specialist should be consulted.


Pyrazines and their Benzo Derivatives

A.E.A. Porter, in Comprehensive Heterocyclic Chemistry, 1984


2.14.2.3 Reactions with Radicals

Homolytic aromatic substitution of the diazines and benzodiazines appears to have been a little used phenomenon and information on such reactions in the pyrazine, quinoxaline and phenazine series is scarce, although in the case of pyrazine and quinoxaline the positions α to the ring nitrogen atoms appear to be the major site of attack 〈72BSF1173〉. Recent work on the substitution of pyrazine and quinoxaline with radicals generated by the oxidation of formamide 〈70TL15〉 indicate that the reaction has some preparative potential in that the corresponding carboxamides may be prepared in good yield; thus, pyrazine yields pyrazinecarboxamide in yields >80% (based on consumed starting material).

The combination of sulfadiazine and pyrimethamine is probably the best means of treating active disease; folinic acid can be added to avoid hematological toxicity without impairing the chemotherapeutic effect. HIV patients with a CD4 count o200 should receive TMP/SMX prophylaxis to prevent reactivation of T. gondii. Atovaquone may be added to inhibit another metabolic path of the organism. Treatment of pregnant women is complicated by drug toxicity to the more sensitive fetus. If infection is confirmed in the first 18 weeks of pregnancy, treatment with spiramycin is recommended to prevent vertical transmission. Spiramycin does not cross the placenta and is not recommended for treating fetal infection. If fetal infection is confirmed by PCR of amniotic fluid or by ultrasound, therapy with pyrimethamine, sulfadiazine, and folinic acid is recommended. Clindamycin is sometimes substituted in the presence of hypersensitivity for one of the drugs mentioned, but it does not penetrate well into the CNS. For the best current drug combination and doses, a competent recent review or infectious disease specialist should be consulted.

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  The structure of 2,4-(4′-aminobenzenamine)pyrimidine (1), a pyrimidine alkaloid previously isolated from the bulbs of Scilla madeirensis (Asparagaceae, synonym Autonoë madeirensis), has been revised. These conclusions were met via comparison of reported NMR and EIMS data with those obtained from synthetic standards. The Sulfad structure is the antibiotic sulfadiazine (2), which has likely been isolated as a contaminant from the site of collection. The reported bioactivity of 1 as an α1-adrenoceptor antagonist should instead be ascribed to sulfadiazine. Our findings appear to show another example of an anthropogenic contaminant being identified as a natural product and emphasize the importance of considering the biosynthetic origins of isolated compounds within a phylogenetic context. The reported isolation of the analgesic tramadol from the roots of the African medicinal plant Nauclea latifolia Sm. (Rubiaceae) in 2013 (1) garnered substantial attention from the scientific communi...
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Sulfad

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  Sulfadiazine is a short-acting sulfonamide. It is readily absorbed from the gastrointestinal tract and rapidly excreted by the kidney. As with other sulfonamides, there are few specific indications because of the wide range of safer and more effective alternative antibiotics. In addition, the emergence of resistance to the sulfonamides has rendered this drug class unsuitable for the treatment of many infections that responded to them in the past. Sulfadiazine is used Sulfad to treat urinary tract infections and as an adjunct for the treatment of a few parasitic diseases. Although sulfadiazine, like other sulfonamides, is fairly well tolerated, its use is associated with adverse effects. Hypersensitivity reactions and gastrointestinal upset are among the common side effects associated with sulfadiazine. Fundamentals: Ligands, Complexes, Synthesis, Purification, and Structure Z. Xu, L.K. Thompson, in Comprehensive Coordination Chemistry II, 2003 1.5.2.1 Overview Diazine (N–N) brid...
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Sulfad

ছবি
  Sulfadiazine is a short-acting sulfonamide. It is readily absorbed from the gastrointestinal tract and rapidly excreted by the kidney. As with other sulfonamides, there are few specific indications because of the wide range of safer and more effective alternative antibiotics. In addition, the emergence of resistance to the sulfonamides has rendered this drug class unsuitable for the treatment of many infections that responded to them in the past. Sulfadiazine is used Sulfad to treat urinary tract infections and as an adjunct for the treatment of a few parasitic diseases. Although sulfadiazine, like other sulfonamides, is fairly well tolerated, its use is associated with adverse effects. Hypersensitivity reactions and gastrointestinal upset are among the common side effects associated with sulfadiazine. Fundamentals: Ligands, Complexes, Synthesis, Purification, and Structure Z. Xu, L.K. Thompson, in Comprehensive Coordination Chemistry II, 2003 1.5.2.1 Overview Diazine (N–N) brid...
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