化合物信息

ID:396

基本信息

化学结构

分子式

C₁₈H₂₅NO

分子量

271.3972

精确质量

271.19361443

电荷

InChI

InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1

InChIKey

MKXZASYAUGDDCJ-NJAFHUGGSA-N

Canonic Smiles

COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2)N(CC1)C

Isomeric Smiles

[C@@]123c4c(C[C@@H]([C@H]1CCCC3)N(CC2)C)ccc(c4)OC

计算属性

JChem

LogD (pH = 7.4)

1.08

LogD (pH = 5.5)

0.05

Log P

3.49

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

9.85

极化表面积

12.47

极化性

31.70

摩尔折射率

82.56

LOG S

-2.92

数据来源

学术数据

数据来源

名称和标识

别名

Levomethorphane [INN-French]DextrometorphanDextromorphanLevomethorphanum [INN-Latin]DextromethorphanDemorphineDemorphanDextromethorphan BromhydrateDextromethorfan [Czech]L-MethorphanDemorphan HydrobromideLevomethorphan [Ban:Dcf:Inn]Delta-MethorphanDextromethorphan BromideD-Methorphan HydrobromideDexyromethorphanLevomethorphanD-MethorphanDextrometorfano [INN-Spanish]Destrometerfano [Dcit]Levometorfano [INN-Spanish]destrometerfanoDXMBA-2666D-methorphand-Methorphan(+)-3-methoxy-N-methylmorphinandextromethorfanBA 2666(9alpha,13alpha,14alpha)-3-methoxy-17-methylmorphinandextromethorphan

名称和标识

数据登录号

PubChem CID

5360696

PubChem SID

1609638593297388198145861

CAS号

125-71-3

PubMed文献链接

181984717976530815818217461892175731159705419108693982426996517157116266026315505150310947461816019312711372

ACToR数据库

125-71-3

MetaboLights数据库

MTBLS2105MTBLS2291MTBLS1115MTBLS2406

DrugBank ID

DB00514

MassBank数据库

EA282410EA282403EA282406EA282408EA282412EA282405EA282413EA282402EA282407EA282414EA282404EA282401EA282411EA282409

Drug Central Database

842

维基百科标题

Dextromethorphan

LINCS数据库

LSM-2726

CHEBI ID

CHEBI:92579CHEBI:4470

KEGG ID

C06947

SABIO-RK数据库

1320813207

BindingDB数据库

50366613

Reactom Database

R-HSA-9728747R-HSA-9679816R-HSA-76456R-HSA-9728748R-HSA-9728752

BRENDA数据库

CHEMBL

BRENDA Ligand数据库

CompTox数据库

BKMS React数据库

SureChEMBL数据库

Reaxys Registry

GeneOntology数据库

KEGG DRUG Database

HMDB数据库

数据登录号

化合物性质

理化性质

疏水性(logP)

3.6

溶解度

74.7 mg/L

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

DrugBank

DB00514

Drug Groups

approved

Description

The d-isomer of the codeine analog of levorphanol. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem]

Indication

For treatment and relief of dry cough.

Pharmacology

Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6.

Absorption

Rapidly absorbed from the gastrointestinal tract.

Half Life

3-6 hours

References

• Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. [Pubmed]

• Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. [Pubmed]

• Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9. [Pubmed]

• Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6. [Pubmed]

• Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

描述信息

参考文献

PubChem文献

数据源提供

• Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

数据来源

• 学术数据

名称和标识

• 别名

• 商标名

• IUPAC传统名

• IUPAC标准名

• 国际非专利药品(INN)

名称和标识

数据登录号

• PubChem CID

• PubChem SID

• CAS号

• 专利号

• PubMed文献链接

• ACToR数据库

• MetaboLights数据库

• DrugBank ID

• MassBank数据库

• Drug Central Database

• 维基百科标题

• LINCS数据库

• CHEBI ID

• KEGG ID

• SABIO-RK数据库

• BindingDB数据库

• Reactom Database

• BRENDA数据库

• CHEMBL

• BRENDA Ligand数据库

• CompTox数据库

• BKMS React数据库

• SureChEMBL数据库

• Reaxys Registry

• GeneOntology数据库

• KEGG DRUG Database

• HMDB数据库

• 理化性质

• DrugBank

• ChEBI

参考文献

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

ACToR数据库

125-71-3

Drug Central Database

维基百科标题

LINCS数据库

SABIO-RK数据库

BindingDB数据库

BRENDA数据库

BRENDA Ligand数据库

CompTox数据库

BKMS React数据库

SureChEMBL数据库

Reaxys Registry

GeneOntology数据库

KEGG DRUG Database

HMDB数据库

理化性质

疏水性(logP)

3.6

溶解度

74.7 mg/L

数据源提供

• Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. Pubmed

别名

DrugBank

DB00514

Drug Groups

approved

Description

Indication

For treatment and relief of dry cough.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6.

Absorption

Rapidly absorbed from the gastrointestinal tract.

Half Life

3-6 hours

References

• Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

商标名

MetroratPertussin DM Extra StrengthHihustan M.DormetanTusilanAntussanCosylanDelsymBenylin DM 12 HourHold DMCreo-TerpinBenylin Pediatric Cough SuppressantDormethanRobitussin Pediatric Cough SuppressantTrocalRobitussin PediatricBenylin DM for Children 12 HourDiabe-Tuss DM SyrupPertussin CS Children's StrengthDelsym Cough FormulaTussadeMediconRomilarTriaminic DM Long Lasting for ChildrenNovahistex DMMethorphanNovahistine DMVicks 44 Cough ReliefBenylin DMSucrets 4 Hour Cough SuppressantBenylin DM for ChildrenCalmylin #1Robitussin Maximum Strength Cough SuppressantBalminil DMCough-XBenylin Adult Formula Cough SuppressantBalminil DM ChildrenKoffex DMMethorate HydrobromideCanfodionCalmylinDextromorphanAlbutussin

IUPAC传统名

dextromethorphan (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-triene

IUPAC标准名

(1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene

国际非专利药品(INN)

dextrometorfanodextromethorphanedextromethorphanumdextromethorphan

ChEBI

CHEBI:4470

A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.