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アムリノン

Amrinone

HCID 3698
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
60719-84-8
標準SMILES
Nc1cc(-c2ccncc2)c[nH]c1=O
InChIKey
RNLQIBCLLYYYFJ-UHFFFAOYSA-N
分子式
C10H9N3O
平均分子量
187.2 g/mol
単同位体質量
187.07456192

概要

Amrinone is a 3,4'-bipyridine substituted at positions 5 and 6 by an amino group and a keto function respectively. A pyridine phosphodiesterase 3 inhibitor, it is a drug that may improve the prognosis in patients with congestive heart failure. It has a role as a cardiovascular drug and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.

名称と識別子

優先名称
Amrinone
IUPAC
3-amino-5-pyridin-4-yl-1H-pyridin-2-one
現地名
アムリノン
英語名
Amrinone
分子式
C10H9N3O
分子量
187.2

名称と別名

Amrinone60719-84-8inamrinoneCartonicAmcoralVesistolAmrinonaAmrinonumWIN 40680DTXSID9022603[3,4'-Bipyridin]-6(1H)-one, 5-amino-5-Amino(3,4'-bipyridin)-6(1H)-one
名称をさらに表示
イソコールイノコール5-アミノ-[3,4'-ビピリジン]-6(1H)-オンコルデムクラベシストールアムリノン5-アミノ-1,6-ジヒドロ-3,4'-ビピリジン-6-オンウィンコラム5-アミノ-3,4'-ビピリジン-6(1H)-オンアムリノン (イナムリノン)イナムリノンアムリノン (JAN)5-アミノ-1,6-ジヒドロ-[3,4'-ビピリジン]-6-オン5-アミノ-3,4′-ビピリジン-6(1H)-オン5-アミノ-[3,4′-ビピリジン]-6(1H)-オン5-アミノ-1,6-ジヒドロ-3,4′-ビピリジン-6-オンアムコラルinocorAmrinonwin40680WincoramImrinoneawd08-250Amirinone
NSC-759805CHEBI:2686JUT23379TN(3,4'-BIPYRIDIN)-6(1H)-ONE, 5-AMINO-C01CE013-amino-5-(pyridin-4-yl)pyridin-2-ol5-Amino[3,4'-bipyridin]-6(1H)-oneDTXCID602603

物性

構造計算による物性

XLogP
-0.2
極性表面積
68 Ų
水素結合供与体数
2
水素結合受容体数
3
回転可能結合数
1
重原子数
14
形式電荷
0
複雑度
300

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LogP0.54
Solubility · 2 件

5.60e+00 g/L

>28.1 [ug/mL] (The mean of the results at pH 7.4)

Human DrugsPharmaceuticals
Melting Point · 2 件

294-297

295 °C

Physical DescriptionSolid
Collision Cross Section · 3 件

142.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID9022603]

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

133.57 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
294 · 294-297°C (dec.)
沸点
321.94 °C · 321.94°C (rough estimate)
比重(密度)
1.2025 · 1.2025 (rough estimate)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

wgk
3
rtecs
DW2500000
ridadr
UN 2811 6.1/PG 3
毒性
LD50 orl-rat: 102 mg/kg NDADD8 1,259,83
hs_code
29333999
risk_code
25-36/37/38-20/21/22
hazard_code
T,Xn
safety_code
28-45-36-26
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 3 Oral
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

ATC Code · 2 件

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding10 to 49%
PharmacodynamicsAmrinone is a positive inotropic cardiotonic with vasodilator properties, phosphodiesterase inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.
Mechanism of ActionAmrinone is a phosphodiesterase inhibitor (PDE3), resulting in increased cAMP and cGMP which leads to an increase in the calcium influx like that caused by beta-agonists resulting in increased inotropic effect.
Biological Half-Life5 to 8 hours
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification · 4 件

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Drugs used to cause dilation of the blood vessels.

Compounds that specifically inhibit PHOSPHODIESTERASE 3.

Absorption, Distribution and Excretion · 2 件

The primary route of excretion in man is via the urine as both inamrinone and several metabolites (N-glycolyl, N-acetate, O-glucuronide and N-glucuronide).

1.2 L/kg [normal volunteers]

Cellular LocationsCytoplasm

用途と製造

関連反応

7 件
反応記録を作成
HRID 423226 の反応式
HRID 423226反応物としてuspto-grants-2012_01
HRID 423234 の反応式
HRID 423234反応物としてuspto-grants-2012_01
HRID 1659874 の反応式
HRID 1659874生成物としてuspto-grants-1981_12
HRID 2050076 の反応式
HRID 2050076生成物としてuspto-grants-1980_04
HRID 2050077 の反応式
HRID 2050077反応物としてuspto-grants-1980_04
HRID 2197421 の反応式
HRID 2197421反応物としてuspto-grants-2012_12
HRID 2197429 の反応式
HRID 2197429反応物としてuspto-grants-2012_12

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
60719-84-8
PubChem CID
3698
DTXSID
DTXSID9022603
ChEMBL
CHEMBL12856
ChEBI
CHEBI:2686
UNII
JUT23379TN
EC Number
262-390-0
Nikkaji
J17.949C
屈折率
1.483 · 1.4830 (estimate)
貯蔵温度
2 · Keep in dark place,Sealed in dry,2-8°C
溶解性
0.3 mg/ml; · DMF: 0.3 mg/ml; DMSO: 0.5 mg/ml
外見
Crystals
酸解離定数(Pka)
12.05 · 12.05±0.10(Predicted)
色
DMFからの結晶
水溶解度
水またはクロロホルムに不溶。酢酸またはDMFにわずかに溶ける。 DMSOに可溶
主な用途
医薬品
InChI
InChI=1S/C10H9N3O/c11-9-5-8(6-13-10(9)14)7-1-3-12-4-2-7/h1-6H,11H2,(H,13,14)
InChIKey
RNLQIBCLLYYYFJ-UHFFFAOYSA-N
SMILES
C1NC(=O)C(N)=CC=1C1C=CN=CC=1
CAS データベース
60719 · 60719-84-8(CAS DataBase Reference)

化学的性質

化学的特性Crystalline Solid

Use ClassificationPharmaceuticals
応用分野 · 3 件

説明Amrinone is a positive inotropic agent useful in the management of severe congestive heart failure. It is effective even in unresponsive, fully digitalized patients.

使用Amrinone is used for short-term treatment of cardiac insufficiency that does not respond to treatment of other drugs.

一般的な説明During normal heart function, cAMP performsimportant roles in regulating intracellular calcium levels.That is, certain calcium channels and storage sites forcalcium must be activated by cAMP-dependant protein kinases.Because cAMP plays an indirect role in the contractilityprocess, agents that inhibit its degradation will providemore calcium for cardiac contraction. One phosphodiesteraseenzyme that is involved in the hydrolysis of myocardiumcAMP is F-III. Amrinone, 5-amino (3,4 -dipyridin)-6 1 (H)-one (Inocor), possesses positive isotropic effects as aresult of its ability to inhibit this phosphodiesterase. In 1999,the USP Nomenclature Committee and the United StatesAdopted Names (USAN) Council approved changing thenonproprietary name and the current official monograph titleof amrinone to inamrinone. This change in nomenclature wasa result of amrinone being confused with amiodarone becauseof the similarity of the names. This was reported to cause confusionbetween the products that led to medication errors,some of which resulted in serious injury or death.

上流・下流製品情報

上流原料

水素

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