기본 정보
- 표준 SMILES
CCCCNc1cc(C(=O)O)cc(S(N)(=O)=O)c1Oc1ccccc1- InChIKey
MAEIEVLCKWDQJH-UHFFFAOYSA-N- 분자식
- C17H20N2O5S
- 평균 분자량
- 364.4 g/mol
- 단동위원소 질량
- 364.10929292
이름 및 식별자
- 우선 이름
- Bumetanide
- IUPAC
- 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
- 영어명
- Bumetanide
- 분자식
- C17H20N2O5S
- 분자량
- 364.42
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
28395-03-1- PubChem CID
- 2471
- DTXSID
DTXSID5022699- ChEMBL
CHEMBL1072- ChEBI
CHEBI:3213- UNII
- 0Y2S3XUQ5H
- EC Number
- 249-004-6
- Nikkaji
- J3.168B
물성
구조 계산 물성
- XLogP
- 2.8
- 극성 표면적
- 127 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 8
- 무거운 원자 수
- 25
- 형식 전하
- 0
- 복잡도
- 528
실험 및 물리화학적 성질
LogP
2.6
2.6
Solubility
>20 mg/mL (in base)
2.57e-02 g/L
>54.7 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
230-231
230 - 231 °C
Dissociation Constants
3.83
3.6
Collision Cross Section
185.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
195.27 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];168.69 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];193.48 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 230 · 230-2310C
- 끓는 점
- 571.2 · 571.2±60.0 °C(Predicted)
- 밀도
- 1.2812 · 1.2812 (rough estimate)
- 굴절률
- 1.651 · 1.6510 (estimate)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 물에 거의 녹지 않으며, 아세톤과 알코올에 녹고, 염화메틸렌에는 약간 녹습니다. 알칼리 수산화물의 묽은 용액에 용해됩니다.
- 물리적 상태
- Solid
- 산도 계수 (pKa)
- 1 · pK1 3.6, pK2 7.7(at 25℃)
- 색상
- 흰색에서 밝은 노란색
- 수용성
- 에탄올(10mg/ml), DMSO(25mg/ml), 아세톤, 벤젠, 메탄올, 프로필렌 글리콜 및 물(<1mg/ml)에 용해됩니다.
- 주요 응용
- 의약품(소분자)
- InChI
- InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
- InChIKey
- MAEIEVLCKWDQJH-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C1=CC(NCCCC)=C(OC2=CC=CC=C2)C(S(N)(=O)=O)=C1
- EPA
- 3 · Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy- (28395-03-1)
화학적 성질
Crystalline Solid
안전 및 규제
GHS 분류
GHS Classification
Warning
H315 (75%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (75%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H361d (25%): Suspected of damaging the unborn child [Warning Reproductive toxicity]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
독성 정보
Adverse Effects
The most common adverse events associated with bumetanide include hyperuricemia (characteristic of all loop diuretics), hypochloremia, hypokalemia, azotemia, and hyponatremia. Other less common adverse effects include hyperglycemia, increased serum creatinine, muscle weakness, and hearing impairment. Rare but significant or potentially life-threatening adverse reactions include hypotension (including orthostatic hypotension), encephalopathy (in instances of pre-existing hepatic disease), and renal failure. All loop diuretics exhibit potent diuresis capabilities, and excessive amounts can lead to significant diuresis with fluid and electrolyte loss; close medical supervision is necessary when administering these agents.
Toxicity Summary
Extensive or too frequent dosage can lead to acute volume and electrolyte depletion, low circulatory volume with a possibility of vascular thrombosis, and embolism. Symptoms such as weakness, mental confusion, anorexia, lethargy, vomiting, and cramps may occur because of electrolyte depletion. Treatment is with the adequate replacement of fluids and electrolytes, such as adding potassium supplements or potassium-sparing diuretics in case of potassium depletion. Asymptomatic hyperuricemia and slight reversible elevations of BUN and creatinine may also occur, particularly associated with dehydration or patients with renal insufficiency. Bumetanide has shown an increase in urinary calcium with resultant hypocalcemia. Similarly, hypomagnesemia should be measured periodically.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Bumetanide
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;It is unknown if bumetanide is excreted into breastmilk. It should be avoided while breastfeeding a newborn because it may decrease milk flow or completely suppress lactation. Low doses in mothers whose lactation is well established are unlikely to suppress lactation.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information on bumetanide was not found as of the revision date. Intense diuresis, fluid restriction and breast binding have been used to suppress lactation immediately postpartum. The added contribution of the diuretic to the other measures, which are effective in suppressing lactation, has not been studied. No data exist on the effects of loop diuretics on established, ongoing lactation.
안전 데이터
- wgk
- 3
- rtecs
- DG4910000
- 독성
- LD50 i.v. in mice: 330 mg/kg (Oestergaard)
- HS 번호
- 2935904000
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
C03CA02
C - Cardiovascular system;C03 - Diuretics;C03C - High-ceiling diuretics;C03CA - Sulfonamides, plain;C03CA02 - Bumetanide
QC - Cardiovascular system;QC03 - Diuretics;QC03C - High-ceiling diuretics;QC03CA - Sulfonamides, plain;QC03CA02 - Bumetanide
Pharmacodynamics
Bumetanide is a loop diuretic of the sulfamyl category to treat heart failure. It is often used in patients in whom high doses of furosemide are ineffective. There is however no reason not to use bumetanide as a first choice drug. The main difference between the two substances is in bioavailability. Bumetanide has more predictable pharmacokinetic properties as well as clinical effect. In patients with normal renal function, bumetanide is 40 times more effective than furosemide.
Mechanism of Action
Bumetanide interferes with renal cAMP and/or inhibits the sodium-potassium ATPase pump. Bumetanide appears to block the active reabsorption of chloride and possibly sodium in the ascending loop of Henle, altering electrolyte transfer in the proximal tubule. This results in excretion of sodium, chloride, and water and, hence, diuresis.
FDA Pharmacological Classification
0Y2S3XUQ5H
BUMETANIDE
Physiologic Effects [PE] - Increased Diuresis at Loop of Henle
Established Pharmacologic Class [EPC] - Loop Diuretic
Bumetanide is a Loop Diuretic. The physiologic effect of bumetanide is by means of Increased Diuresis at Loop of Henle.
BUMETANIDE
MeSH Pharmacological Classification
Agents that promote the excretion of urine through their effects on kidney function.
Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA.
Absorption, Distribution and Excretion
Bumetanide is completely absorbed (80%), and the absorption is not altered when taken with food. Bioavailability is almost complete.
Oral administration of carbon-14 labeled Bumex to human volunteers revealed that 81% of the administered radioactivity was excreted in the urine, 45% of it as unchanged drug. Biliary excretion of Bumex amounted to only 2% of the administered dose.
0.2 - 1.1 mL/min/kg [preterm and full-term neonates with respiratory disorders];2.17 mL/min/kg [neonates receiving bumetanide for volume overload];1.8 +/- 0.3 mL/min/kg [geriatric subjects];2.9 +/- 0.2 mL/min/kg [younger subjects]
용도 및 제조
응용 분야
용도Bumetanide is a diuretic.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: A member of the class of benzoic acids that is 4-phenoxybenzoic acid in which the hydrogens ortho to the phenoxy group are substituted by butylamino and sulfamoyl groups. Bumetanide is a diuretic, and is used for treatment of oedema associated with congestive heart failure, hepatic and renal disease.
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