Tìm theo
Tapentadol
Các tên gọi khác (4 ) :
  • BN-200
  • CG-5503
  • Nucynta
  • Tapentadol
Thuốc Gốc
Small Molecule
CAS: 175591-23-8
ATC: N02AX06
CTHH: C14H23NO
PTK: 221.3385
Opioid analgesic for treatment of moderate to severe pain. FDA approved on Nov 20, 2008.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C14H23NO
Phân tử khối
221.3385
Monoisotopic mass
221.177964363
InChI
InChI=1S/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3/t11-,14+/m0/s1
InChI Key
InChIKey=KWTWDQCKEHXFFR-SMDDNHRTSA-N
IUPAC Name
3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
Traditional IUPAC Name
tapentadol
SMILES
CC[C@H]([C@@H](C)CN(C)C)C1=CC(O)=CC=C1
Độ hòa tan
7.80e-01 g/l
logP
2.87
logS
-2.5
pKa (strongest acidic)
10.28
pKa (Strongest Basic)
9.6
PSA
23.47 Å2
Refractivity
69.56 m3·mol-1
Polarizability
26.58 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
9.34 - 10.45
Dược Lực Học : Tapentadol is a centrally-acting synthetic analgesic. It is 18 times less potent than morphine in terms of binding to human mu-opioid receptors. It also increases norepinephrine concentrations in the brains of rats via inhibition of norepinephrine reuptake. Selective mu-opioid antagonists like naloxone can block analgesia from tapentadol. It also has not effect on the QT interval.
Cơ Chế Tác Dụng : Opioid analgesic for treatment of moderate to severe pain. FDA approved on Nov 20, 2008. Tapendadol causes large increases in levels of extracellular norepinephrine (NE) due to a dual mechanism of action involving mu opioid receptor (MOR) agonism as well as noradrenaline reuptake inhibition.
Dược Động Học :
▧ Absorption :
Bioavailability, immediate release (IR), 86 mg: 32%; Bioavailability, extended release (ER), 86 mg: 32%; Cmax, IR: 64.2 ng/mL; Cmax, ER: 22.5 ng/mL; T max, IR: 1.5 hours; T max, ER: 5.0 hours; Tapentadol accumulates following multiple repeat doses.
▧ Volume of Distribution :
Following IV administration, volume of distribution is 540 ± 98 L.
▧ Protein binding :
~20%
▧ Metabolism :
97% of the dose is metabolized mostly via conjugation with glucuronic acid to produce glucuronides. Tapentadol is also metabolized into N-desmethyl tapentadol (13%) by CYP2C9 and CYP 2C19. CYP2D6 is involved in the formation of the metabolite, hydroxy tapentadol (2%). All metabolites are inactive.
▧ Route of Elimination :
Tapentadol and its metabolites are excreted almost exclusively (99%) via the kidneys. Approximately 70% (55% O-glucuronide and 15% sulfate of tapentadol) is excreted in conjugated form. A total of 3% of drug was excreted in urine as unchanged drug.
▧ Half Life :
Elimination half-life, IV: 4 hours.
▧ Clearance :
Total clearance = 1530 ± 177 ml/min.
Độc Tính : Oral, rabbit: LD50 = 3200 mg/kg; Oral, mouse: LD50 = 300 mg/kg; Oral, rat: LD50: 980 mg/kg; The most common reasons for discontinuation due to adverse events were dizziness, nausea, vomiting, somnolence, and headache.
Chỉ Định : The immediate-release formulation of tapentadol is indicated for the relief of moderate to severe acute pain. The long-acting formulation serves as a continuous, around-the-clock analgesic that is indicated for the relief of moderate to severe chronic pain or neuropathic pain associated with diabetic peripheral neuropathy.
Tương Tác Thuốc :
  • Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Naproxen Increases the AUC of tapentadol by 17%. These changes are not considered clinically relevant and no change in dose is required.
  • Probenecid Increases the AUC of tapentadol by 57%. These changes are not considered clinically relevant and no change in dose is required.
  • Rasagiline Increases the toxicity of tapentadol by unknown mechanism. Discontinue rasagiline at least 14 days prior to tapentadol administration.
  • Selegiline Increases the toxicity of tapentadol by unknown mechanism. Discontinue selegiline at least 14 days prior to tapentadol administration.
  • Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and tapentadol, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Liều Lượng & Cách Dùng : Solution - Oral - 20 mg/mL
Tablet - Oral - 50 mg, 75 mg, 100 mg
Tablet, extended release - Oral - 50 mg, 100 mg, 150 mg, 200 mg, 250 mg
Dữ Kiện Thương Mại
Nhà Sản Xuất
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB06204
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=9838022
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=47207665
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D06007
ChemSpider
http://www.chemspider.com/Chemical-Structure.8013742.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/35356-525-30
Wikipedia
http://en.wikipedia.org/wiki/Tapentadol
RxList
http://www.rxlist.com/nucynta-drug.htm
Drugs.com
http://www.drugs.com/monograph/tapentadol-hydrochloride.html
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