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76-57-3 分子结构
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(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol

ChemBase编号:203
分子式:C18H21NO3
平均质量:299.36424
单一同位素质量:299.15214354
SMILES和InChIs

SMILES:
O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(OC)cc3)C=C[C@@H]2O
Canonical SMILES:
COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
InChI:
InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChIKey:
OROGSEYTTFOCAN-DNJOTXNNSA-N

引用这个纪录

CBID:203 http://www.chembase.cn/molecule-203.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
IUPAC传统名
(-)-codeine
codeine
商标名
Codicept
Coducept
别名
可待因 溶液
可待因
Codeine solution
Codeine
Codeine anhydrous
L-Codeine
Methylmorphine
Morphine monomethyl ether
Norcodeine, N-Methyl
Norcodine, N-Methyl
Codeine
CAS号
76-57-3
EC号
200-969-1
200-659-6
MDL号
MFCD00190150
PubChem SID
24892819
160963666
46507764
24892429
PubChem CID
5284371
CHEBI ID
16714
ATC码
N02AA59
R05DA04
N02AA79
CHEMBL
485
Chemspider ID
4447447
DrugBank ID
DB00318
IUPHAR配体索引
1673
KEGG ID
C06174
美国药典/FDA物质标识码
Q830PW7520
维基百科标题
Codeine
Medline Plus
a682065

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
Sigma Aldrich
C5901 external link 加入购物车 请登录
C1653 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 13.78274  质子受体
质子供体 LogD (pH = 5.5) -1.9427414 
LogD (pH = 7.4) -0.44837403  Log P 1.3429513 
摩尔折射率 84.6047 cm3 极化性 32.610058 Å3
极化表面积 41.93 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.2  LOG S -2.72 
溶解度 5.77e-01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand 查看数据来源
闪点
11 °C expand 查看数据来源
51.8 °F expand 查看数据来源
疏水性(logP)
1.19 [AVDEEF,A ET AL. (1996)] expand 查看数据来源
RTECS编号
QD0893000 expand 查看数据来源
欧盟危险性物质标志
易燃性(Flammable) 易燃性(Flammable) (F) expand 查看数据来源
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
联合国危险货物编号
1230 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
3 expand 查看数据来源
联合国危险货物等级
3 expand 查看数据来源
联合国危险货物包装类别(PG)
2 expand 查看数据来源
危险公开号
11-23/24/25-39/23/24/25 expand 查看数据来源
22 expand 查看数据来源
安全公开号
36/37 expand 查看数据来源
7-16-36/37-45 expand 查看数据来源
GHS危险品标识
GHS02 expand 查看数据来源
GHS06 expand 查看数据来源
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
Warning expand 查看数据来源
GHS危险声明
H225-H301-H311-H331-H370 expand 查看数据来源
H302 expand 查看数据来源
GHS警示性声明
P210-P260-P280-P301 + P310-P311 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US) expand 查看数据来源
RID/ADR
UN 1230 3/PG 2 expand 查看数据来源
毒品管制信息
Home Office Schedule 2; stupéfiant expand 查看数据来源
USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
给药途径
Oral, intra-rectally, SC, IM expand 查看数据来源
生物利用度
~90% Oral expand 查看数据来源
依赖倾向
Low to moderate expand 查看数据来源
半衰期
2.5–3 h expand 查看数据来源
代谢
Hepatic, via CYP2D6 (cytochrome P450 2D6) expand 查看数据来源
法定药品分级
POM (UK) expand 查看数据来源
S8 (Australia) expand 查看数据来源
Schedule I (Canada) expand 查看数据来源
Schedule II (US) expand 查看数据来源
妊娠期药物分类
C (US) expand 查看数据来源
相关基因信息
human ... CYP2D6(1565), OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522) expand 查看数据来源
浓度
1.0 mg/mL±5% in methanol expand 查看数据来源
级别
analytical standard, for drug analysis expand 查看数据来源
适用性
suitable for 1694 per US EPA expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank -  DB00318 external link
Item Information
Drug Groups illicit; approved
Description An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. [PubChem]
Indication For treatment and management of pain (Systemic), also used as an Antidiarrheal and as a cough suppressant.
Pharmacology Codeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. Codeine, in combination with guaifenesin or iodinated glycerol, is used as a cough suppressant and, as a single agent or in combination with acetaminophen or other products, is used for pain control and as an antidiarrheal agent.
Toxicity Respiratory depression, sedation and miosis and common symptoms of overdose. Other symptoms include nausea, vomiting, skeletal muscle flaccidity, bradycardia, hypotension, and cool, clammy skin. Apnea and death may ensue.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6.
Absorption Well absorbed following oral administration with a bioavailability of approximately 90%.
Half Life 2-4 hours
Protein Binding 7-25%
References
Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. [Pubmed]
Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [Pubmed]
Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  C5901 external link
Biochem/physiol Actions
弱麻醉性镇痛剂,作用机理可能是由于可转化成吗啡,其催眠作用较弱;强效镇咳剂
Sigma Aldrich -  C1653 external link
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1653.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. Pubmed
  • Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. Pubmed
  • Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. Pubmed
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专利

专利

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