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Dextropropoxyphene Hydrochloride

HCID 15424
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
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基本情報

CAS
1639-60-7
標準SMILES
CCC(=O)O[C@](Cc1ccccc1)(c1ccccc1)[C@H](C)CN(C)C.Cl
InChIKey
QMQBBUPJKANITL-MYXGOWFTSA-N
分子式
C22H30ClNO2
平均分子量
375.9 g/mol
単同位体質量
375.1965069

概要

Propoxyphene Hydrochloride is the hydrochloride salt form of the d-isomer of synthetic diphenyl propionate derivative propoxyphene, with narcotic analgesic effect. This agent mimics the effects of the endogenous opiate dextropropoxyphene, by binding to mu receptors located throughout the central nervous system. The binding results in GTP to GDP exchanges on the mu-G-protein complex, by which effector adenylate cyclase is inactivated thereby decreasing intracellular cAMP. This, in turn, inhibits the release of various nociceptive neurotransmitters, such as substance P, gamma-aminobutyric acid (GABA), dopamine, acetylcholine, noradrenaline, vasopressin, and somatostatin. In addition, dextropropoxyphene closes N-type voltage-gated calcium channels and opens calcium-dependent inwardly rectifying potassium channels. This results in hyperpolarization, thereby reducing neuronal excitability, which further decreases the perception of pain.

名称と識別子

優先名称
Dextropropoxyphene Hydrochloride
IUPAC
[(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;hydrochloride

名称と別名

Propoxyphene hydrochlorideDeprancolAlgaphanDextropropoxyphene hydrochloridePropoxyphene HCl1639-60-7DoleneKesso-GesicDepronalDolotardDoloxeneProphene 65
名称をさらに表示
DoraphenAbalginZideronFemadolHarmar(+)-Propoxyphene hydrochlorided-Propoxyphene monohydrochlorideDTXSID6048913

データベース識別子

CAS
1639-60-7
PubChem CID
15424
DTXSID
DTXSID6048913
ChEMBL
CHEMBL1237104
UNII
CB2TL9PS0T
EC Number
216-683-5

物性

構造計算による物性

極性表面積
29.5 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
9
重原子数
26
形式電荷
0
複雑度
397

実験および物理化学的性質

Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Analgesics, Opioid; Narcotics

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

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 47 reports by companies from 6 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationBenzeneethanol, .alpha.-(1R)-2-(dimethylamino)-1-methylethyl-.alpha.-phenyl-, propanoate (ester), hydrochloride, (.alpha.S)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzeneethanol, .alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, propanoate (ester), hydrochloride, [S-(R*,S*)]-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Treatment · 1 件

Attention should be directed first to establishing a patent airway and to restoring ventilation. Mechanically assisted ventilation, with or without oxygen, may be required, and positive pressure respiration may be desirable if pulmonary edema is present. The narcotic antagonist naloxone will markedly reduce the degree of respiratory depression, and 0.4 to 2 mg should be administered promptly, preferably intravenously. If the desired degree of counteraction with improvement in respiratory functions is not obtained, naloxone should be repeated at 2- to 3-minute intervals. The duration of action of the antagonist may be brief. If no response is observed after 10 mg of naloxone have been administered, the diagnosis of propoxyphene toxicity should be questioned. Naloxone may also be administered by continuous intravenous infusion. (L1712)

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Hepatic Route of Elimination: The major route of metabolism is cytochrome CYP3A4 mediated N-demethylation to norpropoxyphene, which is excreted by the kidneys. In 48 hours, approximately 20% to 25% of the administered dose of propoxyphene is excreted via the urine, most of which is free or conjugated norpropoxyphene. Half Life: 6-12 hours

MeSH Pharmacological Classification · 2 件

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.

用途と製造

UsesFor the relief of mild to moderate pain
General Manufacturing InformationBenzeneethanol, .alpha.-[(1R)-2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, 1-propanoate, hydrochloride (1:1), (.alpha.S)-: INACTIVE

関連反応

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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
Health Effects
Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
Exposure RoutesOral
Toxicity Summary · 1 件

Propoxyphene acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Propoxyphene primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as propoxyphene also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

Signs and SymptomsComa, respiratory depression, circulatory collapse, and pulmonary edema. Seizures occur more frequently in patients with propoxyphene intoxication than in those with opiate intoxication.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Propoxyphene hydrochloride

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 230mg/kg (oral, rat)