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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 664
実験および物理化学的性質
Human Drugs
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
- 安定性
- Hygroscopic
- InChIKey
- IFGIYSGOEZJNBE-NIWJRJBUNA-N
- SMILES
- O[C@]12CCC(=O)[C@]3([H])OC4=C(C=CC5C[C@@]1([H])[N+](C)(CC1CC1)CC[C@@]23C4=5)O.[Br-] |&1:1,6,15,25,r|
化学的性質
化学的特性Pale Pink Solid
安全と法規制
GHS分類
GHS Classification
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
毒性情報
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Methylnaltrexone bromide
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
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
- safety_code
- 45-61
- Hazard Classifications
- STOT SE 2 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
A06AH01
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
FDA Pharmacological Classification
METHYLNALTREXONE BROMIDE
Opioid Antagonists [MoA]; Quaternary Ammonium Compounds [CS]; Opioid Antagonist [EPC]
応用分野
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).
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