Tìm theo
Dextromethorphan
Các tên gọi khác (10 ) :
  • d-Methorphan
  • delta-Methorphan
  • Dextromethorfan
  • Dextromethorphan
  • Dextrométhorphane
  • Dextromethorphanum
  • Dextrometorfano
  • DM
  • DMHM
  • DXM
Thuốc tác dụng trên đường hô hấp
Thuốc Gốc
Small Molecule
CAS: 125-71-3
ATC: R05DA09
ĐG : Amend
CTHH: C18H25NO
PTK: 271.3972
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]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C18H25NO
Phân tử khối
271.3972
Monoisotopic mass
271.193614427
InChI
InChI=1/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+/s2
InChI Key
InChIKey=MKXZASYAUGDDCJ-HPAQEFICNA-N
IUPAC Name
(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene
Traditional IUPAC Name
levomethorphan
SMILES
[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2
Độ tan chảy
122-124
Độ hòa tan
74.7 mg/L
logP
3.6
logS
-4.5
pKa (Strongest Basic)
9.85
PSA
12.47 Å2
Refractivity
82.56 m3·mol-1
Polarizability
31.74 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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] Dextromethorphan is an opioid-like drug that binds to and acts as antagonist to the NMDA glutamatergic receptor, it is an agonist to the opioid sigma 1 and sigma 2 receptors, it is also an alpha3/beta4 nicotinic receptor antagonist and targets the serotonin reuptake pump. Dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan.
Dược Động Học :
▧ Absorption :
Rapidly absorbed from the gastrointestinal tract.
▧ Metabolism :
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.
▧ Half Life :
3-6 hours
Chỉ Định : For treatment and relief of dry cough.
Tương Tác Thuốc :
  • Abiraterone Abiraterone increases levels by affecting CYP2D6 metabolism. Interaction is significant so monitor closely.
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Dihydroquinidine barbiturate Quinidine increases the toxicity of dextromethorphan
  • Fluoxetine Combination associated with possible serotoninergic syndrome
  • Isocarboxazid Possible severe adverse reaction
  • Moclobemide Increased CNS toxicity
  • Paroxetine Combination associated with possible serotoninergic syndrome
  • Phenelzine Possible severe adverse reaction
  • Quinidine Quinidine increases the toxicity of dextromethorphan
  • Quinidine barbiturate Quinidine increases the toxicity of dextromethorphan
  • Rasagiline Possible severe adverse reaction
  • Selegiline Combination associated with possible serotoninergic syndrome
  • Sibutramine Combination associated with possible serotoninergic syndrome
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Dextromethorphan. Consider alternate therapy or monitor for therapeutic/adverse effects of Dextromethorphan if Terbinafine is initiated, discontinued or dose changed.
  • Tocilizumab Dextromethorphan is a CYP2D6 and CYP3A4 substrate. Exposure of dextromethorphan decreases following administration of tocilizumab.
  • Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Tranylcypromine Increased risk of serotonin syndrome. Concomitant use should be avoided.
  • Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Vemurafenib Vemurafenib increases the AUC (CYP2D6 substrate) by 47% .
  • Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Vilazodone Consideration should be given to avoiding the concomitant use of dextromethorphan and selective serotonin reuptake inhibitors (SSRI). Monitor for toxic effects of dextromethorphan (eg, CNS, Cardiovascular) if an SSRI is initiated or the dose is increased. SSRIs, other than fluoxetine and paroxetine, may be safer alternatives due to lesser CYP2D6 inhibition; however, the mechanism for the interaction is not fully understood, and caution is still advised.
  • Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and dextromethorphan, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Liều Lượng & Cách Dùng : Capsule - Oral
Liquid - Oral
Lozenge - Oral
Strip - Oral
Suspension - Oral
Syrup - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Rougier
    Sản phẩm biệt dược : Balminil DM
  • Công ty : McNeil
    Sản phẩm biệt dược : Benylin DM
  • Sản phẩm biệt dược : Delsym
  • Công ty : Rougier
    Sản phẩm biệt dược : Koffex DM
  • Công ty : Bayer
    Sản phẩm biệt dược : Romilar
  • Công ty : Novartis
    Sản phẩm biệt dược : Triaminic
  • Công ty : Procter & Gamble
    Sản phẩm biệt dược : Vicks Formula 44
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00514
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06947
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D03742
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/63824-171-63
PharmGKB
http://www.pharmgkb.org/drug/PA449273
Wikipedia
http://en.wikipedia.org/wiki/Dextromethorphan
Drugs.com
http://www.drugs.com/dextromethorphan.html
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