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Dihydrocodeine

HCID 5284543
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
125-28-0
標準SMILES
COc1ccc2c3c1O[C@H]1[C@@H](O)CC[C@H]4[C@@H](C2)N(C)CC[C@@]341
InChIKey
RBOXVHNMENFORY-DNJOTXNNSA-N
分子式
C18H23NO3
平均分子量
301.4 g/mol
単同位体質量
301.1677936

概要

Dihydrocodeine is a morphinane alkaloid.

名称と識別子

優先名称
Dihydrocodeine
IUPAC
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol

名称と別名

DIHYDROCODEINERapacodinNovicondinCodhydrineDehacodinHydrocodeine8,14-DihydroneopineDihidrocodeinaDihydroneopineCohydrinalpha-Hydrocodol125-28-0
名称をさらに表示
DrocodeDihydrocodeinumDiidrocodeinaRemedacenDH-codeineN9I9HDB855IDS-ND-008(SECT.2)NSC-231319

データベース識別子

CAS
125-28-0
PubChem CID
5284543
DTXSID
DTXSID5022936
ChEMBL
CHEMBL1595
ChEBI
CHEBI:135276
UNII
N9I9HDB855
EC Number
204-732-3
Nikkaji
J5.368F

物性

構造計算による物性

XLogP
2.2
極性表面積
41.9 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
1
重原子数
22
形式電荷
0
複雑度
471

実験および物理化学的性質

Drugs · 5 件

DEA NFLIS-Drug Category -> Narcotic Analgesics

DEA Schedule II Controlled Substance -> Opiates

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Listed in ZINC15

Human Drugs · 2 件

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

Pharmaceuticals

Endocrine DisruptorsPotential endocrine disrupting compound
Dissociation Constants8.75
Collision Cross Section168.6 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

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+H311+H331 (90.7%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P233, P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P316, P321, P330, P333+P317, P342+P316, P361+P364, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

DEA schedule II controlled substance

REACH registered substance: Dihydrocodeine (EC: 204-732-3)

Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Drug Induced Liver Injury · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Dihydrocodeine

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals · 6 件

Dihydrocodeine

3.7

15.8

Dihydrocodeine bitartrate is given in combination with acetaminophen and caffeine in a capsule (as Trezix), with 16 mg dihydrocodeine bitartrate per capsule. The usual adult dosage is 2 Trezix capsules orally every 4 hours, as needed. No more than 5 doses, or 10 capsules should be taken in a 24-hour period.

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

PharmacodynamicsPossible opioid related side effects include, but are not limited to, drowsiness, nausea, headache, dry mouth, constipation, difficulty passing urine, and mild euphoria.
Mechanism of ActionDihydrocodeine is metabolized to dihydromorphine -- a highly active metabolite with a high affinity for mu opioid receptors. [3]
Biological Half-Life4h
Metabolism/Metabolites · 2 件

Metabolized in the liver by CYP 2D6 into an active metabolite, dihydromorphine, and by CYP 3A4 into secondary primary metabolite, nordihydrocodeine. A third primary metabolite is dihydrocodeine-6-glucuronide. [1] The time for mean peak concentration in acid metabolites is 1.76h and 1.98h for a 30 and 60mg dose, respectively. The concentrations achieved were 563 ug/1 and 1476 ug/1, respectively. [2]

Dihydrocodeine has known human metabolites that include Desmethyl dihydrocodeine and Paramorfan.

FDA Pharmacological Classification · 5 件

N9I9HDB855

DIHYDROCODEINE

Mechanisms of Action [MoA] - Full Opioid Agonists

Established Pharmacologic Class [EPC] - Opioid Agonist

Dihydrocodeine is an Opioid Agonist. The mechanism of action of dihydrocodeine is as a Full Opioid Agonist.

MeSH Pharmacological ClassificationCompounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Absorption, Distribution and Excretion · 4 件

Bioavailability is low (approximately 20%) if administered orally. This may be due to poor gastrointestinal absorption. It is also likely due to pre-systemic metabolism by the liver and intestinal wall. [2] The AUCs after oral and intravenous administration are similar (3203ug/l/h and 3401ug/l/h, respectively). [2] Time to peak values are 1.6 and 1.8hours for a 30mg and 60mg dose, respectively. The concentrations achieved were 71.8 ug/1 and 146 ug/1, respectively. [2]

関連反応

3 件
反応記録を作成
HRID 1293510 の反応式
HRID 1293510反応物としてuspto-grants-2007_07
HRID 2375508 の反応式
HRID 2375508反応物としてuspto-grants-2008_12
HRID 2380554 の反応式
HRID 2380554生成物として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

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 160 mg/day, Lowest Therapeutic Dose (LTD): 2.0 mg/kg-day, and Screening Dose: 0.0007 mg/kg-day.

1-Feb-20

Renal elimination and urinary excretion. [1]

The disposition of dihydrocodeine is described as a two compartment model. [2]

Plasma clearance is approximately 300ml/min. [2] The pharmacokinetics of dihydrocodeine and active metabolite dihydromorphine have been reported to be linear. [1] The decline in plasma dihydrocodeine concentrations after intravenous administration has been described as bi-exponential, with a sleep decline in the initial 2h following administration, followed by a mono-exponential decline thereafter. Clearance was not dose dependent. [2]

用途と製造

UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationPharmaceuticals