Bumetanide

HCID 2471CAS 28395-03-1

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

bumetanide28395-03-13-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acidBumexBurinexBumetanidaRo 10-6338BumetanidumLixil3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acidPF 1593Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-
이름 더 보기
pf159DONALDburineBufenoxfontego
PF-1593DTXSID5022699PF1593Ro-10-63380Y2S3XUQ5HCHEBI:3213Bumethanide3-butylamino-4-phenoxy-5-sulfamoylbenzoic acid

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

실험 및 물리화학적 성질

LogP · 2건

2.6

2.6

Solubility · 3건

>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 · 2건

230-231

230 - 231 °C

Physical DescriptionSolid
Dissociation Constants · 2건

3.83

3.6

Collision Cross Section · 2건

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.

화학적 성질

Crystalline Solid

안전 및 규제

GHS 분류

GHS Classification · 5건

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

Other Safety InformationIMAP assessments - Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-: Human health tier I assessment;IMAP assessments - Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (75%);Eye Irrit. 2A (75%);STOT SE 3 (75%);Repr. 2 (25%)

독성 정보

Adverse Effects · 1건

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 · 1건

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 · 6건

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 · 1건

◉ 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 · 3건

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

Protein Binding97%
Pharmacodynamics · 1건

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 · 1건

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.

Biological Half-Life60-90 minutes
Metabolism/Metabolites45% is secreted unchanged. Urinary and biliary metabolites are formed by oxidation of the N-butyl side chain.

용도 및 제조

UsesUse (kg) in USA (2002): 86;Consumption (g per capita) in the USA (2002): 0.000303;Calculated removal (%): 25.3
Use ClassificationPharmaceuticals

응용 분야

용도Bumetanide is a diuretic.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
苏州朗恩生物科技有限公司13921996628 · [email protected]
추가 설명 · 1건

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.

관련 반응

34건

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