홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /화합물

Flumazenil

HCID 3373
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
78755-81-4
표준 SMILES
CCOC(=O)c1ncn2c1CN(C)C(=O)c1cc(F)ccc1-2
InChIKey
OFBIFZUFASYYRE-UHFFFAOYSA-N
분자식
C15H14FN3O3
평균 분자량
303.29 g/mol
단동위원소 질량
303.10191953

개요

Flumazenil is an organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose. It has a role as a GABA antagonist and an antidote to benzodiazepine poisoning. It is an imidazobenzodiazepine, an ethyl ester and an organofluorine compound.

이름 및 식별자

우선 이름
Flumazenil
IUPAC
ethyl 8-fluoro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate
영어명
Flumazenil
분자식
C15H14FN3O3
분자량
303.29

이름 및 동의어

flumazenil78755-81-4AnexateFlumazepilRomaziconLanexatMaziconRo-15-1788FlumazenilumFlumazeniloDTXSID2023064Ro 151788
이름 더 보기
FMZethyl 8-fluoro-5-Methyl-6-oxo-5,6-dihydro-4H-benzo[f]iMidazo[1,5-a][1,4]diazepine-3-carboxylateYM-684Ro 1722RO 15-1788
RO-151788NSC-759193DTXCID703064Ro 15-1788/000Ro-15-1788/0004H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester40P7XK9392RO-1722

데이터베이스 식별자

CAS
78755-81-4
PubChem CID
3373
DTXSID
DTXSID2023064
ChEMBL
CHEMBL407
ChEBI
CHEBI:5103
UNII
40P7XK9392
EC Number
616-650-9
Nikkaji
J23.594F

물성

구조 계산 물성

XLogP
1
극성 표면적
64.4 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
5
회전 가능 결합 수
3
무거운 원자 수
22
형식 전하
0
복잡도
461

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Various

LogP · 2건

1.9

1.26

Solubility1.04e+00 g/L
Human Drugs · 3건

Breast Feeding; Lactation; Milk, Human; Antidotes; GABA Modulators; Benzodiazepines

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 2건

201-203 °C

201 - 203 °C

Physical DescriptionSolid
Collision Cross Section · 3건

164.31 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

165.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

165.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

물리화학적 성질

녹는점
201 · 201-203°C
끓는 점

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.

Warning

H302 (80%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (80%)

독성 정보

Adverse EffectsSerious Adverse Events
Toxicity SummaryFlumazenil has some associations with the precipitation of seizures in patients with benzodiazepine dependency with a history of seizures. However, flumazenil overdose is extremely rare.
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Flumazenil

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
2
rtecs
NI2922170
독성
LD50 in mice, rats (mg/kg): 4000, 1360 i.p.; 4300, 6000 orally (Hunkeler)
HS 번호
2933997500

화학 및 산업

약리 정보

ATC Code · 2건

V - Various

QV - Various

Protein BindingProtein binding is approximately 50%, mostly (66%) to albumin. Protein binding is reduced in patients with hepatic cirrhosis.
Pharmacodynamics · 1건

Flumazenil antagonizes the CNS effects produced by benzodiazepines, but does not antagonize the central nervous system effects of drugs affecting GABA-ergic neurons by means other than the benzodiazepine receptor (including ethanol, barbiturates, or general anesthetics) and does not reverse the effects of opioids.

Mechanism of Action · 1건

Flumazenil, an imidazobenzodiazepine derivative, is a benzodiazepine antagonist. It competitively inhibits the benzodiazepine binding site on the GABA/benzodiazepine receptor complex. Flumazenil is a weak partial agonist in some animal models of activity, but has little or no agonist activity in man.

Biological Half-Life · 1건

Initial distribution half-life is 4 to 11 minutes and the terminal half-life is 40 to 80 minutes. Prolongation of the half-life to 1.3 hours in patients with moderate hepatic impairment and 2.4 hours in severely impaired patients. Compared to adults, the elimination half-life in pediatric patients was more variable, averaging 40 minutes (range: 20 to 75 minutes).

Metabolism/MetabolitesHepatic. Flumazenil is completely (99%) metabolized. The major metabolites of flumazenil identified in urine are the de-ethylated free acid and its glucuronide conjugate.
FDA Pharmacological Classification · 6건

40P7XK9392

FLUMAZENIL

Established Pharmacologic Class [EPC] - Benzodiazepine Antagonist

Flumazenil is a Benzodiazepine Antagonist.

FLUMAZENIL

Benzodiazepine Antagonist [EPC]

MeSH Pharmacological Classification · 2건

관련 반응

68건
반응 기록 만들기
HRID 67291 반응식
HRID 67291반응물로uspto-grants-1982_08
HRID 67292 반응식
HRID 67292반응물로uspto-grants-1982_08
HRID 67293 반응식
HRID 67293반응물로uspto-grants-1982_08
HRID 67294 반응식
HRID 67294반응물로uspto-grants-1982_08
HRID 67295 반응식
HRID 67295반응물로uspto-grants-1982_08
HRID 67299 반응식
HRID 67299생성물로uspto-grants-1982_08
HRID 67342 반응식
HRID 67342반응물로uspto-grants-1982_08
HRID 67343 반응식
HRID 67343반응물로uspto-grants-1982_08
1 / 9 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
528 · 528.0±50.0 °C(Predicted)
밀도
1.39 · 1.39±0.1 g/cm3(Predicted)
저장 조건
2 · Sealed in dry,2-8°C
용해도
25 mM까지 · DMSO에서 25mM까지 용해 가능
물리적 상태
고체
산도 계수 (pKa)
0.86 · 0.86±0.20(Predicted)
색상
하얀색
수용성
128 mg/L · 128mg/L
Merck
14 · 14,4135
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
주요 응용
의약품(소분자)
InChI
InChI=1S/C15H14FN3O3/c1-3-22-15(21)13-12-7-18(2)14(20)10-6-9(16)4-5-11(10)19(12)8-17-13/h4-6,8H,3,7H2,1-2H3
InChIKey
OFBIFZUFASYYRE-UHFFFAOYSA-N
SMILES
N12C=NC(C(OCC)=O)=C1CN(C)C(=O)C1=CC(F)=CC=C12
NIST
Flumazenil(78755-81-4)

화학적 성질

Flumazenil is a white to off-white crystalline compound with an octanol:buffer partition coefficient of 14 to 1 at pH 7.4. It is insoluble in water but slightly soluble in acidic aqueous solutions.

risk_code
36/37/38
hazard_code
Xi
safety_code
26-27-36/37/39
스토리지 클래스
11 - Combustible Solids

Agents counteracting or neutralizing the action of POISONS.

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.

Absorption, Distribution and Excretion · 3건

Flumazenil is completely (99%) metabolized. Elimination of radiolabeled drug is essentially complete within 72 hours, with 90% to 95% of the radioactivity appearing in urine and 5% to 10% in the feces.

0.9 to 1.1 L/kg

1 L/hr/kg [healthy volunteers receiving a 5-minute infusion of a total of 1 mg]

Cellular LocationsMembrane

응용 분야

개요Flumazenil is a benzodiazepine antagonist useful as a fast-acting antidote in the treatment of benzodiazepine intoxication, and in reversing the central sedative effects of benzodiazepines during anesthesia.

용도Flumazenil is an imidazodiazepine which selectively blocks the central effects of classic benzodiazepines. It is used as benzodiazepine antagonist sedation reversal drug.

제조 방법 · 1건

The Synthesis of FlumazenilStarting with 4-fluoroaniline (15) the isatin 17 is synthesized via the Sandmeyer synthesis; isatin is then oxidized with peracetic acid to the isatoic anhydride 18. Reaction with sarcosine in DMF leads to the benzodiazepine-2,5-dione 19. This is converted to the iminochloride by reaction with POCI3 . In the key step the imidazoester is built up by reaction with deprotonated ethyl isocyanoacetate [8]. Since ethyl isocyanoacetate is not very stable, an alternative synthesis based on the synthesis of midazolam was developed for large scale-production. Tnthis synthesis diethylmalonate is used. The diester 21 is then transformed to the monoester 22 hy deethoxycarbonylation. Nitrosation and catalytic reduction lead to the amino compound 23. The final carbon atom is introduced by reaction with the orthoester.

상·하류 제품 정보

상류 원료

6-플루오로이사토산무수물과산화 수소5-플루오로이사틴N,N-디메틸아닐린소디움-t-부톡시드안트라닐산사르코신에틸 사이아노아세테이트아세트산 칼륨

하류 제품

4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-
추가 설명 · 1건

정의ChEBI: Flumazenil is an organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose. It has a role as a GABA antagonist and an antidote to benzodiazepine poisoning. It is an ethyl ester, an organofluorine compound and an imidazobenzodiazepine.