Azosemide
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기본 정보
- CAS
27589-33-9- 표준 SMILES
NS(=O)(=O)c1cc(-c2nn[nH]n2)c(NCc2cccs2)cc1Cl- InChIKey
HMEDEBAJARCKCT-UHFFFAOYSA-N- 분자식
- C12H11ClN6O2S2
- 평균 분자량
- 370.8 g/mol
- 단동위원소 질량
- 370.00734327
개요
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.
이름 및 식별자
- 우선 이름
- Azosemide
- IUPAC
- 2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- 영어명
- Azosemide
- 분자식
- C12H11ClN6O2S2
- 분자량
- 370.84
이름 및 동의어
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
이름 더 보기
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
데이터베이스 식별자
- CAS
27589-33-9- PubChem CID
- 2273
- DTXSID
DTXSID7046910- ChEMBL
CHEMBL1097235- ChEBI
CHEBI:31248
물성
구조 계산 물성보충 중
- XLogP
- 1.5
- 극성 표면적
- 163 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 23
- 형식 전하
- 0
- 복잡도
- 504
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point219.5 °C
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 218 · 218-221°
- 끓는 점
- 221 °C · 221°C (rough estimate)
- 밀도
- 1.6843 · 1.6843 (rough estimate)
- 굴절률
- 1.61 · 1.6100 (estimate)
- 저장 조건
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- 용해도
- DMSO(약간 용해됨), 메탄올(약간 용해됨, 가열)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 3.58 · 3.58±0.10(Predicted)
- 색상
- 크리스탈
- 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
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- 독성
- LD50 orl-rat: 2545 mg/kg IYKEDH 18,666,87
화학 및 산업
약리 정보
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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