Azosemide (HCID 2273)

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

データベース識別子

CAS: 27589-33-9
PubChem CID: 2273
DTXSID: DTXSID7046910
ChEMBL: CHEMBL1097235
ChEBI: CHEBI:31248
UNII: MR40VT1L8Z
EC Number: 248-549-7
Nikkaji: J10.727A

物性

構造計算による物性

XLogP: 1.5
極性表面積: 163 Å²
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
CAS データベース: 27589 · 27589-33-9(CAS DataBase Reference)

安全と法規制

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.

応用分野 · 3 件

用途ループ利尿薬尿の排泄を増大させる薬物で，うっ血性心不全，高血圧症，各種浮腫などに使用される

説明Azosemide is a high-ceiling diuretic similiar in structure and profile to furosemide, albeit somewhat less potent and less bioavailable. It is useful in the treatment of congestive heart failure and similar edematous conditions.

使用Diuretic.

上流・下流製品情報

上流原料

アジ化ナトリウムベンゾニトリル 2-thiophene

サプライヤー50 社

Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]

杭州品高化工有限公司0571-87658025 · [email protected]

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

補足説明 · 1 件

定義ChEBI: 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 hyp rtension.