基本情報
- CAS
309-29-5- 標準SMILES
CCN1CC(CCN2CCOCC2)C(c2ccccc2)(c2ccccc2)C1=O- InChIKey
XFDJYSQDBULQSI-UHFFFAOYSA-N- 分子式
- C24H30N2O2
- 平均分子量
- 378.5 g/mol
- 単同位体質量
- 378.2307282
概要
Doxapram is a member of the class of pyrrolidin-2-ones that is N-ethylpyrrolidin-2-one in which both of the hydrogens at the 3 position (adjacent to the carbonyl group) are substituted by phenyl groups, and one of the hydrogens at the 4 position is substituted by a 2-(morpholin-4-yl)ethyl group. A central and respiratory stimulant with a brief duration of action, it is used (generally as the hydrochloride or the hydrochloride hydrate) as a temporary treatment of acute respiratory failure, particularly when superimposed on chronic obstructive pulmonary disease, and of postoperative respiratory depression. It has also been used for treatment of postoperative shivering. It has a role as a central nervous system stimulant. It is a member of morpholines and a member of pyrrolidin-2-ones.
名称と識別子
- 優先名称
- Doxapram
- IUPAC
- 1-ethyl-4-(2-morpholin-4-ylethyl)-3,3-diphenylpyrrolidin-2-one
- 現地名
- ドキサプラム
- 英語名
- Doxapram
- 分子式
- C24H30N2O2
- 分子量
- 378.51
名称と別名
doxapram309-29-5DoxapramumDocatone2-Pyrrolidinone, 1-ethyl-4-[2-(4-morpholinyl)ethyl]-3,3-diphenyl-1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinone(+-)-doxapram2-Pyrrolidinone, 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-oneCHEBI:6818482-Pyrrolidinone, 1-ethyl-4-(2-(4-morpholinyl)ethyl)-3,3-diphenyl-94F3830Q73
名称をさらに表示
4-[2-(1-エチル-5-オキソ-4,4-ジフェニル-3-ピロリジニル)エチル]モルホリン1-エチル-4-(2-モルホリノエチル)-3,3-ジフェニル-2-ピロリジンオン1-エチル-4-(2-モルホリノエチル)-3,3-ジフェニル-2-ピロリドン1-エチル-4-(2-モルホリノエチル)-3,3-ジフェニルピロリジン-2-オンドキサプラム1-エチル-4-[2-(モルホリン-4-イル)エチル]-3,3-ジフェニルピロリジン-2-オンahr619DopramdopreamAHR-619DOXOPRAMRespiramDoxapram USP/EP/BPDOPRAMSTIMULEXRESPIRAMDoxapram (AHR-619, Dopram, Stimulex or Respiram)
物性
構造計算による物性
- XLogP
- 3.3
- 極性表面積
- 32.8 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 6
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 487
実験および物理化学的性質
LogP3.6
Solubility
Sparingly soluble
WHITE TO OFF-WHITE CRYSTALLINE POWDER; PRACTICALLY INSOL IN ETHER /HYDROCHLORIDE/
3.43e-02 g/L
Human DrugsPharmaceuticals
Melting Point
217-219
MP: 123-124 °C /BENZOATE/
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN LIGHT & IN AIR /HYDROCHLORIDE/
Collision Cross Section
183.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
185 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
Other Experimental PropertiesCRYSTALS FROM ISOPROPYL ETHER; BITTER TASTE; MP: 217-219 °C; SOL IN WATER; SPARINGLY SOL IN ALC; SLIGHTLY SOL IN CHLOROFORM /HYDROCHLORIDE/
物理化学的性質
- 融点
- 113 · 113 - 114°C
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
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesEye Irrit. 2 (100%)
毒性情報
Human Toxicity Excerpts...SIDE EFFECTS INDICATIVE OF SUBCONVULSIVE CNS STIMULATION /ARE/... HYPERTENSION, TACHYCARDIA, ARRHYTHMIAS, COUGHING, SNEEZING, VOMITING, ITCHING, TREMORS, MUSCLE RIGIDITY, SWEATING, FLUSHING, & HYPERPYREXIA.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
doxapram
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts
OVERDOSAGE /OF DOXAPRAM TO DOGS/ CAUSED CONSTRICTION OF CEREBRAL VESSELS & REDUCED CEREBRAL BLOOD FLOW & PRODUCED TISSUE ANOXIA SECONDARY TO RESP STIMULATION & LOSS OF CO2. PETECHIAL & PERIVASCULAR HEMORRHAGES WERE FOUND THROUGHOUT BRAIN, BUT...HISTOLOGIC EXAM SHOWED NO ABNORMALITY IN EYES OR OPTIC NERVES. /HYDROCHLORIDE/
安全データ
- 有毒物質データの
- 309-29-5(Hazardous Substances Data)
化学と産業
薬理情報
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Doxapram is an analeptic agent (a stimulant of the central nervous system). The respiratory stimulant action is manifested by an increase in tidal volume associated with a slight increase in respiratory rate. A pressor response may result following doxapram administration. Provided there is no impairment of cardiac function, the pressor effect is more marked in hypovolemic than in normovolemic states. The pressor response is due to the improved cardiac output rather than peripheral vasoconstriction. Following doxapram administration, an increased release of catecholamines has been noted.
Mechanism of Action
Doxapram produces respiratory stimulation mediated through the peripheral carotid chemoreceptors. It is thought to stimulate the carotid body by inhibiting certain potassium channels.
DOXAPRAM...STIMULATE ALL LEVELS OF CEREBROSPINAL AXIS. ADEQUATE DOSES PRODUCE TONIC-CLONIC CONVULSIONS SIMILAR IN PATTERN TO THOSE PRODUCED BY PENTYLENETETRAZOL. ...ACT BY ENHANCING EXCITATION RATHER THAN BY BLOCKING CENTRAL INHIBITION.
Biological Half-LifeAFTER IV DOXAPRAM-HCL BOLUS INJECTIONS OR BRIEF INFUSIONS IN HEALTHY VOLUNTEER, PLASMA CONCN DECLINED IN MULTI-EXPONENTIAL FASHION. HALF-LIFE FROM 4-12 HR WAS 3.4.
Metabolism/Metabolites
DOXAPRAM YIELDS 4-(2-MORPHOLINOETHYL)-3,3-DIPHENYLPYRROLIDIN-2-ONE, & 1-ETHYL-4-(2-(3-OXOMORPHOLINO)ETHYL)-3,3-DIPHENYLPYRROLIDIN-2-ONE IN DOGS. PITTS, JE, BRUCE, RB, & FOREHAND, JB, XENOBIOTICA, 3, 73 (1973). /FROM TABLE/
AFTER IV DOXAPRAM-HCL BOLUS INJECTIONS OR BRIEF INFUSIONS IN HEALTHY VOLUNTEERS, A METABOLITE AHR 5955 WAS PRESENT IN PLASMA IN AMT COMPARABLE TO PARENT COMPD & HAD A SIMILAR HALF-LIFE.
FDA Pharmacological Classification
94F3830Q73
DOXAPRAM
Physiologic Effects [PE] - Increased Medullary Respiratory Drive
Established Pharmacologic Class [EPC] - Respiratory Stimulant
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