基本情報
- 標準SMILES
Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1- InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N- 分子式
- C10H10N4O2S
- 平均分子量
- 250.28 g/mol
- 単同位体質量
- 250.05244656
概要
Sulfadiazine is a sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antimicrobial agent, an antiinfective agent, a xenobiotic, a coccidiostat, an antiprotozoal drug, an EC 2.5.1.15 (dihydropteroate synthase) inhibitor, an EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor, an environmental contaminant and a drug allergen. It is a sulfonamide, a member of pyrimidines, a substituted aniline and a sulfonamide antibiotic. It is functionally related to a sulfanilamide. It is a conjugate acid of a sulfadiazinate.
名称と識別子
- 優先名称
- Sulfadiazine
- IUPAC
- 4-amino-N-pyrimidin-2-ylbenzenesulfonamide
- 現地名
- スルファダイアジン
- 英語名
- Sulfadiazine
- 分子式
- C10H10N4O2S
- 分子量
- 250.28
名称と別名
名称をさらに表示
データベース識別子
- CAS
68-35-9- PubChem CID
- 5215
- DTXSID
DTXSID7044130- ChEMBL
CHEMBL439- ChEBI
CHEBI:9328- UNII
- 0N7609K889
- EC Number
- 200-685-8
- Nikkaji
- J1.418D
物性
構造計算による物性
- XLogP
- -0.1
- 極性表面積
- 106 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 6
- 回転可能結合数
- 3
- 重原子数
- 17
- 形式電荷
- 0
- 複雑度
- 327
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics (Sulfonamide)
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
-0.2
-0.04
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Anti-infective medicines
Animal Drugs
Active Ingredients (Sulfadiazine) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section
153.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
150.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
148.7 Ų [M+H]+ [CCS Type: TW]
157.85 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
151.96 Ų [M+H]+
物理化学的性質
- 融点
- 253 °C · 253 °C (dec.) (lit.)
- 沸点
- 512.6 · 512.6±52.0 °C(Predicted)
- 比重(密度)
- 1.378 · 1.3780 (rough estimate)
- 屈折率
- 1.644 · 1.6440 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- ジメチルスルホキシドに可溶。
- 酸解離定数(Pka)
- 2.21 · pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
- 外見
- 粉
- 色
- 白い
- 水溶解度
- 67.13 mg/L · 67.13mg/L(25℃)
- Merck
- 14 · 14,8903
- BRN
- 6733588 · 6733588
- BCS Class
- 4 · 4/3
- 主な用途
- 臨床検査
- InChI
- 1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
- InChIKey
- SEEPANYCNGTZFQ-UHFFFAOYSA-N
- SMILES
- Nc1ccc(cc1)S(=O)(=O)Nc2ncccn2
- CAS データベース
- 68 · 68-35-9(CAS DataBase Reference)
- NISTの化学物質情報
- Sulfadiazine(68-35-9)
- EPAの化学物質情報
- 4 · Benzenesulfonamide, 4-amino-N-2-pyrimidinyl- (68-35-9)
化学的性質
化学的特性White to slightly yellow crystalline pow
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 1.2% (2 of 171) of reports.
Danger
H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P233, P260, P261, P263, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 171 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Status: Active Update: 23-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17511
Sulphadiazine: Does not have an individual approval but may be used under an appropriate group standard
毒性情報
Hepatotoxicity
Sulfadiazine, like other sulfonamides, causes a characteristic idiosyncratic liver injury which has features of drug-allergy or hypersensitivity. The typical onset is sudden development of fever and rash followed by jaundice within a few days or weeks of starting the medication. The pattern of injury is typically mixed, although fatal cases are often hepatocellular and prolonged cholestatic cases have also been described. Eosinophilia or atypical lymphocytosis are also common and the clinical pattern can be considered a part of DRESS syndrome (drug rash with eosinophilia and systemic symptoms). Cases of Stevens Johnson syndrome due to sulfadiazine have also been described. Sulfonamides such as sulfadiazine have been linked to many cases of acute liver failure and as a class, the sulfonamides still rank in the top 5 to 10 causes of drug induced, idiosyncratic fulminant hepatic failure. However, most cases of sulfonamide induced liver injury resolve rapidly, usually within 2 to 4 weeks unless cholestasis is severe. Onset of injury is more rapid with rechallenge and can appear within a day or reexposure. Patients with hepatic injury due to sulfadiazine may have a history of previous exposure to the drug without injury. Sulfonamides such as sulfadiazine can also cause mild and transient ALT elevations that do not progress to jaundice or more severe liver injury either alone or as a part of a generalized hypersensitivity reaction. Sulfonamides have also been linked to hepatic granulomas.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sulfadiazine
vLess-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
安全データ
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- WP1925000
- ridadr
- 3249
- 毒性
- LD50 oral in mouse: 1500mg/kg
- hs_code
- 29335990
- risk_code
- 22-36/37/38-42/43-43-42
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- hazard_class
- 6.1(b)
- packing_group
- III
- 環境リスク評価
- スルファジアジン(68-35-9)
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Repr. 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
J01EC02
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01EC02
Pharmacodynamics
Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of <i>p</i>-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Mechanism of Action
Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
FDA Pharmacological Classification
0N7609K889
SULFADIAZINE
Established Pharmacologic Class [EPC] - Sulfonamide Antibacterial
Chemical Structure [CS] - Sulfonamides
Sulfadiazine is a Sulfonamide Antibacterial.
SULFADIAZINE
MeSH Pharmacological Classification
Substances that are destructive to protozoans.
Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals.
Substances that inhibit the growth or reproduction of BACTERIA.
用途と製造
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Antiinfectives for systemic use -> Antibacterials for systemic use -> Sulfonamides and trimethoprims -> Intermediate-acting sulfonamides -> Antibiotics
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
応用分野
解説スルファダイアジンは,サルファ剤の一種。ぶどう球菌・大腸菌などに抗菌力を持ち、皮膚の細菌感染症や肺炎・赤痢などに用いる。小学館 デジタル大辞泉について 情報 | 凡例
用途スルファジアジン(Sulfadiazine)は、サルファ薬の一つ。感染源の細菌細胞内での葉酸の合成を阻害することによって殺す効果があり、尿路感染症(UTIs)の治療に使われる。 スルファジアジンとピリメタミンとの組み合わせは、トキソプラズマ(Toxoplasma gondii)が原因のトキソプラズマ症の治療に使われる。
用途細菌性下痢症、ヘモフィルス感染症 (豚) 。
使用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.
一般的な説明Sulfadiazine’s plasma half-life is 17 hours. It is a white,odorless crystalline powder soluble in water to the extentof 1:8,100 at 37°C and 1:13,000 at 25°C, in human serumto the extent of 1:620 at 37°C, and sparingly soluble in alcoholand acetone. It is readily soluble in dilute mineralacids and bases. Its pKa is 6.3.
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.
関連反応
関連ノート
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