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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/30 16:38:53」(JST)

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The structure of the sulfonamide group

In chemistry, the sulfonamide functional group (also spelt sulphonamide) is -S(=O)₂-NH₂, a sulfonyl group connected to an amine group. Relatively speaking this group is unreactive. The amine center is no longer basic. The S-N bond is cleaved only with difficulty. Because of the rigidity of the functional group, sulfonamides are typically crystalline. For this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group.^[1]

A sulfonamide (compound) is a compound that contains this group. The general formula is RSO₂NH₂, where R is some organic group. For example, "methanesulfonamide" is CH₃SO₂NH₂. Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group with an amine group. In medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or variation of sulfanilamide. The first sulfonamide was discovered in Germany in 1932.^[2]

Synthesis

Sulfonamides can be prepared in the laboratory in many ways. The classic approach entails the reaction of sulfonyl chlorides with an amines.

RSO₂Cl + R₂NH → RSO₂NR₂ + HCl

A base such as pyridine is typically added to absorb the HCl that is generated. Illustrative is the synthesis of sulfonylmethylamide.^[3] A readily available sulfonyl chloride source is tosyl chloride.^[4] The reaction of primary and secondary amines with benzenesulfonyl chloride is the basis of the Hinsberg reaction, a method for detecting primary and secondary amines.

Triflimide or triflimidic acid HN(Tf)₂ (bis(trifluoromethane)sulfonimide) is the formal adduct of triflic acid and ammonia. Phenyl triflimide is a triflating reagent. The related metal triflimidates are used as catalysts. The anion bistriflimide is hydrophobic.

Sultams

Sultams are cyclic sulfonamides. Bioactive sultams include the antiinflammatory ampiroxicam and the anticonvulsant sultiame. Sultams are prepared analogously to other sulfonamides, allowing for the fact that sulfonic acids are deprotonated by amines. They are often prepared by one-pot oxidation of disulfides or thiols linked to amines.^[5]

Sulfonamide-based compounds
Sulfanilamide, a compound that foreshadowed the development of sulfa drugs.
Sulfamethoxazole is a widely used antibiotic sulfa drug.
Ampiroxicam is a sultam used as an antiinflammatory drug.
Hydrochlorothiazide is a drug that features both acyclic and cyclic sulfonamide groups.
Camphorsultam is a sultam used as a chiral auxiliary in organic synthesis.

Sulfinamides

The related sulfinamides (R(S=O)NHR) are amides of sulfinic acids (R(S=O)OH) (see sulfinyl). Chiral sulfinamides such as tert-butanesulfinamide, p-toluenesulfinamide ^[6]^[7] and 2,4,6-trimethylbenzenesulfinamide ^[8] are relevant to asymmetric synthesis.

Disulfonimides

The related disulfonimides are of the type R-S(=O)₂-N(H)-S(=O)₂-R' with two sulfonyl groups flanking an amine.^[9] As with sulfinamides this class of compounds is used as catalysts in enantioselective synthesis.^[9]^[10]^[11]

References

^ Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. (2005), "Chemotherapeutics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_173
^ Levy, Stuart B. (2002). The antibiotic paradox : how the misuse of antibiotics destroys their curative powers (2 ed.). Cambridge, Mass.: Perseus Publ. p. 51. ISBN 9780738204406.
^ Organic Syntheses, Coll. Vol. 4, p.943 (1963); Vol. 34, p.96 (1954). Online Article
^ Organic Syntheses, Coll. Vol. 5, p.39 (1973); Vol. 48, p.8 (1968). Online Article
^ Rassadin, V.; Grosheva, D.; Tomashevskii, A. Sokolov, V. "Methods of Sultam Synthesis" Chemistry of Heterocyclic Compounds 2013, Vol. 49, p39-65. 27. doi:10.1007/s10593-013-1231-3.
^ Organic Syntheses, Coll. Vol. 10, p.47 (2004); Vol. 77, p.50 (2000). Link
^ Org. Synth 2007, 84, 129-138 Link
^ Org. Synth. 2006, 83, 131-140 Link
^ ^a ^b Development and Applications of Disulfonimides in Enantioselective Organocatalysis Thomas James, Manuel van Gemmeren, and Benjamin List Chem. Rev., 2015 doi:10.1021/acs.chemrev.5b00128
^ Treskow, M., Neudörfl, J. and Giernoth, R. (2009), BINBAM – A New Motif for Strong and Chiral Brønsted Acids. Eur. J. Org. Chem., 2009: 3693–3697. doi:10.1002/ejoc.200900548
^ García-García, P., Lay, F., García-García, P., Rabalakos, C. and List, B. (2009), A Powerful Chiral Counteranion Motif for Asymmetric Catalysis. Angew. Chem. Int. Ed., 48: 4363–4366. doi:10.1002/anie.200901768

UpToDate Contents

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1. HIVに感染していない患者のスルホンアミド系薬剤アレルギー sulfonamide allergy in hiv uninfected patients
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English Journal

Monitoring and determination of sulfonamide antibiotics (sulfamethoxydiazine, sulfamethazine, sulfamethoxazole and sulfadiazine) in imported Pangasius catfish products in Thailand using liquid chromatography coupled with tandem mass spectrometry.

Jansomboon W1, Boontanon SK2, Boontanon N3, Polprasert C4, Thi Da C5.
Food chemistry.Food Chem.2016 Dec 1;212:635-40. doi: 10.1016/j.foodchem.2016.06.026. Epub 2016 Jun 11.
This research aimed to monitor the concentrations of sulfamethoxydiazine (SMD), sulfamethazine (SMT), sulfamethoxazole (SMX) and sulfadiazine (SDZ) in imported Pangasius catfish products in Thailand. The residues of the four sulfonamides (SAs) were analyzed by extraction process and liquid chromatog
PMID 27374578

Synthesis of novel sulfonamides under mild conditions with effective inhibitory activity against the carbonic anhydrase isoforms I and II.

Başar E1, Tunca E2, Bülbül M2, Kaya M2.
Journal of enzyme inhibition and medicinal chemistry.J Enzyme Inhib Med Chem.2016 Dec;31(6):1356-61. doi: 10.3109/14756366.2015.1134524. Epub 2016 Jan 27.
Novel sulfonamide derivatives 6a-i, as new carbonic anhydrase inhibitors which candidate for glaucoma treatment, were synthesized from the reactions of 4-amino-N-(4-sulfamoylphenyl) benzamide 4 and sulfonyl chloride derivatives 5a-i with high yield (71-90%). The structures of these compounds were co
PMID 27541741

Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides.

Gul HI1, Tugrak M1, Sakagami H2, Taslimi P3, Gulcin I3,4, Supuran CT5.
Journal of enzyme inhibition and medicinal chemistry.J Enzyme Inhib Med Chem.2016 Dec;31(6):1619-24. doi: 10.3109/14756366.2016.1160077. Epub 2016 Mar 30.
A series of new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides (7-12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1-6) and 4-hydrazinobenzenesulfonamide. The substituted benzaldehydes from which the key intermediat
PMID 27028783

Japanese Journal

Creation of Novel Toxic Gas Surrogates and the Development of Safe and Facile Catalytic Reactions

ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 66(1), 1-19, 2018
NAID 130006301021

An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity

ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 65(3), 248-252, 2017
NAID 130005397369

A review of toxic epidermal necrolysis management in Japan

Allergology International 66(1), 36-41, 2017
NAID 130005308397

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★リンクテーブル★

リンク元	「抗菌薬」「急性尿細管間質性腎炎」「メトヘモグロビン」「スルホンアミド系抗菌薬」

「抗菌薬」

　　[★]

英: antibacterial drug, antibacterial
関: 抗生剤、薬理学、抗菌薬一覧、抗細菌薬

first aid step 1 2006 p.165

定義

細菌/微生物に静菌作用、殺菌作用を示す物質。結果として、人において病原性を除去する目的で使用される。
このうち、微生物によって産生される物質を抗生物質と呼ぶ

作用機序による分類

細胞壁合成阻害：βラクタム系抗菌薬(ペニシリン系抗菌薬、セフェム系抗菌薬、モノバクタム系抗菌薬、カルバペネム系抗菌薬)
核酸合成阻害　：ニューキノロン系抗菌薬、メトロニダゾール
タンパク質合成阻害

30S：アミノグリコシド系抗菌薬、テトラサイクリン系抗菌薬
50S：マクロライド系抗菌薬、クリンダマイシン、クロラムフェニコール、ストレプトグラミン系抗菌薬、オキソゾリニドン系抗菌薬(リゾネリド)

代謝拮抗：サルファ剤(サルファメソキサゾール、トリメトプリム)

first aid step 1 2006 p.165

	Mechanism of action	Drugs
1	Block cell wall synthesis by inhibition of peptidoglycan cross-linking	penicillin, ampicillin, ticarcillin, piperacillin, imipenem, aztreonam, cephalosporins
2	Block peptidoglycan synthesis	bacitracin, vancomycin, cycloserine
3	Disrupt bacterial/fungal cell membranes	polymyxins
4	Disrupt fungal cell membranes	amphotericin B, nystatin, fluconazole/azoles
5	Block nucleotide synthesis	sulfonamides, trimethoprim
6	Block DNA topoisomerases	quinolones
7	Block mRNA synthesis	rifampin
8	Block protein synthesis at 50S ribosomal subunit	chloramphenicol, erythromycin/macrolides, lincomycin, clindamycin, streptogramins (quinupristin, dalfopristin), linezolid
9	Block protein synthesis at 30S ribosomal subunit	aminoglycosides, tetracyclines, spectinomycin 　ATuSi　→　あつし

薬物動態

濃度依存性：アミノグリコシド系抗菌薬、ニューロキノロン系抗菌薬
時間依存性：βラクタム系抗菌薬

治療期間

小児

尾内一信 ; 第 39 回日本小児感染症学会教育講演 2 小児感染症の抗菌薬療法 -耐性菌時代の適正使用-

感染臓器・臨床診断	原因菌	投与期間（抗菌薬）
髄膜炎	インフルエンザ菌	7-10日
	肺炎球菌	10-14日
	髄膜炎菌	7-10日
	GBS，腸内細菌，リステリア	21日
中耳炎	＜2 歳	10日
中耳炎	2 歳≦	5-7日
咽頭炎	A 群連鎖球菌	10日(ペニシリン系薬)
咽頭炎	A 群連鎖球菌	5日(セフェム系薬)
肺炎	肺炎球菌，インフルエンザ菌	解熱後3-4日
	黄色ブドウ球菌	3-4週間
	マイコプラズマ，クラミジア	10-21日
腎臓、膀胱炎、腎盂腎炎	大腸菌，プロテウス，腸球菌	3日
腎臓、膀胱炎、腎盂腎炎	大腸菌，プロテウス，腸球菌	14日
骨髄炎	黄色ブドウ球菌	21日
骨髄炎	連鎖球菌，インフルエンザ菌	14日

主要な感染症の抗菌薬投与期間

感染レジマニュ p.27

骨	骨髄炎		4-6週
耳鼻咽喉	中耳炎		5-7日
	副鼻腔炎		5-14日
	A群溶連菌咽頭炎		10日
肺	肺炎	肺炎球菌	7-10日 or 解熱後3日間
		インフルエンザ菌	10-14日
		マイコプラズマ	14日(7-10日)
		レジオネラ	21日
	肺化膿症		28-42日
心臓	感染性心内膜炎	α連鎖球菌	2-4週
		黄色ブドウ球菌	4-6週
消化管	腸炎	赤痢菌	3日
		チフス	14日(5-7日)
		パラチフス
	腹膜炎	特発性	5日
		二次性	10-14日
胆肝膵	肝膿瘍	細菌性	4-8週
		アメーバ性	10日
尿路	膀胱炎		3日
	急性腎盂腎炎		14日(7-10日)
	急性腎盂腎炎・再発		6週
	慢性前立腺炎		1-3ヶ月
髄腔	髄膜炎	インフルエンザ菌	7-10日
		髄膜炎菌
		肺炎球菌	10-14日
		リステリア	21日
敗血症	敗血症	コアグラーゼ陰性ブドウ球菌	5-7日
		黄色ブドウ球菌	28日(14日)
		グラム陰性桿菌	14日(7-14日)
		カンジダ	血液培養陰性化後, 14日