基本信息
- 标准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
- 单同位素质量
- 370.00734327
概述
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.
名称与标识
- 首选名称
- Azosemide
- IUPAC
- 2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- 中文名
- 阿佐酰胺
- 英文名
- Azosemide
- 分子式
- C12H11ClN6O2S2
- 分子量
- 370.84
名称与别名
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
展开更多名称
阿佐寒米阿佐塞米阿佐酰胺阿佐酰胺标准品阿佐塞米 HPLCAzosemide试剂Azosemide试剂阿佐塞米溶液,1000PPM阿佐塞米溶液, 100PPM阿佐酰胺,10 MM DMSO 溶液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
数据库标识
- CAS
27589-33-9- PubChem CID
- 2273
- DTXSID
DTXSID7046910- ChEMBL
CHEMBL1097235- ChEBI
CHEBI:31248- UNII
- MR40VT1L8Z
- EC Number
- 248-549-7
- Nikkaji
- J10.727A
性质
结构计算性质
- XLogP
- 1.5
- 极性表面积
- 163 Ų
- 氢键供体
- 3
- 氢键受体
- 8
- 可旋转键
- 5
- 重原子
- 23
- 形式电荷
- 0
- 复杂度
- 504
实验与物化性质
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point219.5 °C
Physical DescriptionSolid
物理化学性质
- 熔点
- 218 · 218-221°
- 沸点
- 221 °C · 221°C (rough estimate)
- 密度
- 1.6843 · 1.6843 (rough estimate)
- 折射率
- 1.61 · 1.6100 (estimate)
- 储存条件
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- 溶解度
- DMSO (Slightly), Methanol (Slightly, Heated)
- 形态
- Solid
- 酸度系数(pKa)
- 3.58 · 3.58±0.10(Predicted)
- 颜色
- Crystals
- 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
- CAS 数据库
- 27589 · 27589-33-9(CAS DataBase Reference)
化学性质
结晶，熔点220-223℃。
安全与法规
安全数据
- 毒性
- LD50 orl-rat: 2545 mg/kg IYKEDH 18,666,87
毒性防护
急性毒性口服-大鼠 LD50: 2545 毫克/公斤; 口服-小鼠 LD50: 6350 毫克/公斤
包装储运
可燃性危险特性可燃; 燃烧产生有毒氮氧化物, 硫氧化物和氯化物烟雾
储运特性通风低温干燥
灭火剂干粉,泡沫,沙土,二氧化碳, 雾状水
化学与工业
药理信息
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
应用领域
概述阿佐塞米化学名为2-氯-5-(1H-四氮唑-5-基)-4-(2-噻吩甲基氨基)苯磺酰胺，是一种髓襻利尿药，能抑制亨利襻升支部分对钠、钾和氯离子的重吸收。1987年其片剂首次在日本上市，用于治疗心源性水肿(充血性心衰)、肾性水肿和肝性水肿。本品为长效型利尿剂，一日只需口服一次。本品口服吸收差，生物利用度为10％，达峰时间约为3h，口服仅2％吸收，脉注射有20％以原药形式随尿排出，口服和静注后的消除半衰期为2-2.5h，略长于其他磺胺类髓襻利尿药。阿佐塞米为日本三和研究所开发，90％市场在日本，已经上市10年以上。
用途利尿药。有抑制盐类再吸收的作用，其降压作用较弱。用于心、肝、肾性浮肿。
用途用作医药中间体
制备方法
生产方法4-氯-2-氟-5-氨磺酰基苯腈和噻吩甲基胺在四氢呋喃中反应，得4-氯-5-氨磺酰基-2-噻吩甲氨基苯腈，熔点170-174℃。再和叠氮钠在氯化铵溶液中反应，即得阿佐塞米，熔点218-221℃，收率37%。
上下游产品信息
上游原料
试剂价格
- HY-107321R · 5 mg
- 阿佐酰胺Azosemide (Standard) — 480元
- HY-107321R · 10 mg
- 阿佐酰胺Azosemide (Standard) — 720元
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