メチルナルトレキソン臭化物

Methylnaltrexone Bromide

HCID 5361917

基本情報

CAS
73232-52-7
標準SMILES
C[N+]1(CC2CC2)CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5.[Br-]
InChIKey
IFGIYSGOEZJNBE-KNLJMPJLSA-N
分子式
C21H26BrNO4
平均分子量
436.3 g/mol
単同位体質量
435.10452041

概要

Methylnaltrexone Bromide is the bromide salt form of methylnaltrexone, a methyl derivative of noroxymorphone with selective, peripherally-acting mu-opioid receptor antagonistic activity. Methylnaltrexone displaces opioids from peripheral opioid receptors in the gastrointestinal tract, the bladder, and the skin, thereby reversing the opioid-related peripheral side-effects, such as constipation, urinary retention, and pruritis, respectively. Unlike naltrexone and due to the presence of a positively charged nitrogen atom in methylnaltrexone, this agent does not cross the blood-brain barrier and does not affect the centrally-mediated analgesic effect of opioids.

名称と識別子

優先名称
Methylnaltrexone Bromide
IUPAC
(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one bromide
現地名
メチルナルトレキソン臭化物
英語名
Naltrexone methylbromide
分子式
C21H26BrNO4
分子量
436.35

名称と別名

Methylnaltrexone bromideRelistorN-Methylnaltrexone BromideNaltrexone methobromideMRZ-2663BRMOA-728bromuro de metilnaltrexonabromure de methylnaltrexoneMRZ2663BRMOA728DTXSID30868236NALTREXONE METHYLBROMIDE
名称をさらに表示
メチルナルトレキソン臭化物メチルナルトレキソン臭化物 (JAN)MNTXUnii-rfo6il3D3mAdamantane Impurity 52Methylnatrexone bromideMethyhaaltrexone broMide
methylnaltrexoni bromidumRefChem:56830A06AH01DTXCID40820845morphinan-17-ium-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-, bromide, (5alpha,17R)-916055-92-0RFO6IL3D3M73232-52-7

データベース識別子

CAS
73232-52-7
PubChem CID
5361917
DTXSID
DTXSID30868236
ChEMBL
CHEMBL1201770
EC Number
615-932-9

物性

構造計算による物性

極性表面積
66.8 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
2
重原子数
27

実験および物理化学的性質

Human Drugs · 4 件

Breast Feeding; Lactation; Milk, Human; Narcotic Antagonists

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

物理化学的性質

融点
237 · 237-239°C
貯蔵温度
-20 °C · -20°C
溶解性
2 O: · H2O: ≥5mg/mL
外見
粉
色
白からベージュ
水溶解度
2 O: · H2O: ≥5mg/mL

化学的性質

化学的特性Pale Pink Solid

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301 (66.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 57 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (66.7%)

毒性情報

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Methylnaltrexone bromide

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk
3
rtecs
QD0188550
ridadr
UN 2811 6.1 / PGIII
hs_code
2934990002
risk_code
25-50
hazard_code
T,N

化学と産業

薬理情報

ATC Code · 3 件

A06AH01

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

FDA Pharmacological Classification · 2 件

METHYLNALTREXONE BROMIDE

Opioid Antagonists [MoA]; Quaternary Ammonium Compounds [CS]; Opioid Antagonist [EPC]

MeSH Pharmacological ClassificationAgents inhibiting the effect of narcotics on the central nervous system.
応用分野 · 3 件

説明The widespread efficacy of opioids in treating patients with moderate to severe acute and chronic pain is often accompanied by untoward side effects. In particular, opioid-induced bowel dysfunction is one of the more common and debilitating consequences afflicting up to 50% of patients. To counteract the peripherally-mediated adverse effects, opioid antagonists such as naloxone, naltrexone, and nalmephene are sometimes prescribed. The latest market entry exploits a strategic modification of naltrexone to lower its lipid solubility and increase its polarity: quaternization of the amine of naltrexone by methylation (methyl bromide) prevents crossing of the blood–brain barrier thereby creating an effective peripheral antagonist. Despite a loss of potency upon methylation, methylnaltrexone antagonizes opioid binding at m-opioid receptors with an IC50 of 70 nM. Its affinity for k-opioid receptors is approximately eightfold less (IC50= 575 nM) with no significant binding to d-opioid, orphanin, or non-opioid receptors. Methylnaltrexone bromide has been approved for the treatment of opioid-induced constipation in patients with advanced illness receiving palliative care.Regarding metabolism, methylnaltrexone bromide is eliminated primarily as intact drug (85% based on administered radioactivity) by slightly more renal than hepatic clearance.The most common adverse events were abdominal pain and flatulence followed by nausea, dizziness, and diarrhea.

使用A metabolite of Naltrexone (N285750). Methylnaltrexone (MNTX), a selective μ-opioid receptor antagonist, functions as a peripherally acting receptor antagonist in tissues of the gastrointestinal tract.

一般的な説明Methylnaltrexone does not cross blood brain barrier and does not affect the opioid effects in the brain, such as analgesia. It is used to treat opioid-induced constipation (OIC).

サプライヤー75 社

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咸宁深蓝生物医药研发有限公司18171815831 · [email protected]

関連反応

5 件

化合物ノート

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