アゾセミド
Azosemide
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基本情報
- CAS
27589-33-9- 標準SMILES
NS(=O)(=O)c1cc(-c2nn[nH]n2)c(NCc2cccs2)cc1Cl- InChIKey
HMEDEBAJARCKCT-UHFFFAOYSA-N- 分子式
- C12H11ClN6O2S2
- 平均分子量
- 370.8 g/mol
- 単同位体質量
- 370.00734327
概要
Azosemide is a sulfonamide that is benzenesulfonamide which is substituted at positions 2, 4, and 5 by chlorine, (2-thienylmethyl)amino and 1H-tetrazol-5-yl groups, respectively. It is a diuretic that has been used in the management of oedema and hypertension. It has a role as a loop diuretic. It is a member of thiophenes, a sulfonamide, a member of tetrazoles and a member of monochlorobenzenes.
名称と識別子
- 優先名称
- Azosemide
- IUPAC
- 2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- 現地名
- アゾセミド
- 英語名
- Azosemide
- 分子式
- C12H11ClN6O2S2
- 分子量
- 370.84
名称と別名
azosemide27589-33-9AzosemidDiartAzosemidaAzosemidumLuretDTXSID7046910MR40VT1L8Z2-Chloro-5-(1H-tetrazol-5-yl)-N(sup 4)-2-thenylsulfanilamideBenzenesulfonamide, 2-chloro-5-(1H-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazole
名称をさらに表示
ダイタリックアゾセリックアゾセミドジアルト2-クロロ-5-(1H-テトラゾール-5-イル)-4-[(2-チエニルメチル)アミノ]ベンゼンスルホンアミドダイアートジウラピドルレットアゾセミド (JAN)2-クロロ-5-(1H-1,2,3,4-テトラゾール-5-イル)-4-{[(チオフェン-2-イル)メチル]アミノ}ベンゼン-1-スルホンアミドSK-110ple1053DiurapidAZOSEMIDE HPLCAzosemide USP/EP/BP
DTXCID5026910CHEBI:312482-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-((thiophen-2-ylmethyl)amino)benzene-1-sulfonamide2-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzene-1-sulfonamide5-(4-chloro-5-sulfamyl-2-thienylaminophenyl)tetrazoleRefChem:5606092-Chloro-5-(1H-tetrazol-5-yl)-4-((thien-2-ylmethyl)amino)benzenesulfonamide248-549-7
物性
構造計算による物性補完中
- XLogP
- 1.5
- 極性表面積
- 163 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 8
- 回転可能結合数
- 5
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 504
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point219.5 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 218 · 218-221°
- 沸点
- 221 °C · 221°C (rough estimate)
- 比重(密度)
- 1.6843 · 1.6843 (rough estimate)
- 屈折率
- 1.61 · 1.6100 (estimate)
- 貯蔵温度
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- 溶解性
- DMSO（微量）、メタノール（微量、加温）
- 外見
- 個体
- 酸解離定数(Pka)
- 3.58 · 3.58±0.10(Predicted)
- 色
- クリスタル
- InChI
- InChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)
- InChIKey
- HMEDEBAJARCKCT-UHFFFAOYSA-N
- SMILES
- C1(S(N)(=O)=O)=CC(C2=NNN=N2)=C(NCC2SC=CC=2)C=C1Cl
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- 毒性
- LD50 orl-rat: 2545 mg/kg IYKEDH 18,666,87
化学と産業
薬理情報
Protein Binding> 95% 4% protein binding to 4% human serum albumin at azosemide concentrations of 10-100ug/ml, using equilibrium dialysis.
PharmacodynamicsDiuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.
Mechanism of ActionExact mechanism of action is unclear. However, it acts primarily on the loop of Henle, in both the medullary and cortical segments of the thick ascending limb.
Biological Half-LifeTerminal half life 2-3 hours.
Metabolism/MetabolitesConsiderable first pass metabolism which makes parentral administration more effective than oral administration. Eleven metabolites of azosemide were found in rats, but only azosemide and its glucuronide were detected in humans.
MeSH Pharmacological ClassificationAgents that promote the excretion of urine through their effects on kidney function.
Absorption, Distribution and Excretion
Peak plasma concentrations are achieved in 3-4 hours when azosemide is administered to healthy humans in a fasting state. There is an absorption lag time of approximately 1 hour. Oral bioavailability estimated to be 20.4%
Total body clearance 112ml/min. Renal clearance 41.6ml/min. Actively secreted in the renal proximal tubule of humans. This may or may not involve a nonspecific organic acid secretory pathway. There is thus a potential for disease states and other organic acids such as NSAIDs which affect the organic acid transport pathway to affect the efficacy of azosemide.
Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg.
Cellular LocationsMembrane
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