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Meperidine Hydrochloride

HCID 5750
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
50-13-5
標準SMILES
CCOC(=O)C1(c2ccccc2)CCN(C)CC1.Cl
InChIKey
WCNLCIJMFAJCPX-UHFFFAOYSA-N
分子式
C15H22ClNO2
平均分子量
283.79 g/mol
単同位体質量
283.1339066

概要

Pethidine hydrochloride is the hydrochloride salt of pethidine. An analgesic used for the treatment of postoperative and labour pain. It has a role as an opioid analgesic, an antispasmodic drug, a mu-opioid receptor agonist and a kappa-opioid receptor agonist. It contains a pethidine(1+).

名称と識別子

優先名称
Meperidine Hydrochloride
IUPAC
ethyl 1-methyl-4-phenylpiperidine-4-carboxylate;hydrochloride

名称と別名

MEPERIDINE HYDROCHLORIDEPethidine hydrochloride50-13-5AntiduolCentralginDispadolDolantalDolestineDolarenAlgilMeperidine HclAntidurol
名称をさらに表示
DoloneurinePetantinPiridosalDolenalDolenolMepadinPetidinDemerol hydrochloride

データベース識別子

CAS
50-13-5
PubChem CID
5750
DTXSID
DTXSID30950620
ChEMBL
CHEMBL1701
ChEBI
CHEBI:31984
UNII
N8E7F7Q170
EC Number
200-013-3

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
4
重原子数
19
形式電荷
0
複雑度
276

実験および物理化学的性質

Human Drugs · 2 件

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 (98.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationMeperidine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (98.6%)

毒性情報

Treatment · 1 件

Primary attention should be given to the reestablishment of adequate respiratory exchange through provision of a patent airway and institution of assisted or controlled ventilation. The narcotic antagonist, naloxone hydrochloride, is a specific antidote against respiratory depression which may result from overdosage or unusual sensitivity to narcotics, including meperidine. Therefore, an appropriate dose of this antagonist should be administered, preferably by the intravenous route, simultaneously with efforts at respiratory resuscitation. An antagonist should not be administered in the absence of clinically significant respiratory or cardiovascular depression. Oxygen, intravenous fluids, vasopressors, and other supportive measures should be employed as indicated. In cases of overdosage with Meperidine tablets, the stomach should be evacuated by emesis or gastric lavage. (L1712)

Health EffectsMedical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Meperidine is metabolized in the liver by hydrolysis to meperidinic acid followed by partial conjugation with glucuronic acid. Meperidine also undergoes N-demethylation to normeperidine, which then undergoes hydrolysis and partial conjugation. Normeperidine is about half as potent as meperidine, but it has twice the CNS stimulation effects. Route of Elimination: Excreted in the urine. The proportion of drug that is excreted unchanged or as metabolites is dependent on pH. When urine pH is uncontrolled, 5-30% of the meperidine dose is excreted as normeperidine and approximately 5% is excreted unchanged. Meperidine and normeperidine are found in acidic urine, while the free and conjugated forms of meperidinic and normperidinic acids are found in alkaline urine. Half Life: Initial distribution phase (t<sub>1/2 &alpha;</sub>) = 2-11 minutes; terminal elimination phase (t<sub>1/2 &beta;</sub>) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t<sub>1/2 &beta;</sub> is prolonged to 7-11 hours.

FDA Pharmacological Classification · 2 件

MEPERIDINE HYDROCHLORIDE

Full Opioid Agonists [MoA]; Opioid Agonist [EPC]

MeSH Pharmacological Classification · 3 件

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

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage.

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

UsesUsed to control moderate to severe pain.

関連反応

2 件
反応記録を作成
HRID 483798 の反応式
HRID 483798反応物としてuspto-grants-1993_07
HRID 2379036 の反応式
HRID 2379036反応物としてuspto-grants-1994_11

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
Exposure Routes · 1 件

Intravenous; oral; parenteral (intramuscular). The oral bioavailability of meperidine in patients with normal hepatic function is 50-60% due to extensive first-pass metabolism. Bioavailability increases to 80-90% in patients with hepatic impairment (e.g. liver cirrhosis). Meperidine is less than half as effective when administered orally compared to parenteral administration. One study reported that 80-85% of the drug administered intramuscularly was absorbed within 6 hours of intragluteal injection in health adults; however, inter-individual variation and patient-specific variable appear to cause considerable variations in absorption upon IM injection.

Toxicity Summary · 1 件

Meperidine is primarily a kappa-opiate receptor agonist and also has local anesthetic effects. Meperidine has more affinity for the kappa-receptor than morphine. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators 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 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.

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)

Meperidine hydrochloride

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015