Tìm theo
Fentanyl
Các tên gọi khác (15 ) :
  • 1-Phenethyl-4-(N-phenylpropionamido)piperidine
  • 1-Phenethyl-4-N-propionylanilinopiperidine
  • Fentanil
  • Fentanila
  • Fentanilo
  • Fentanyl
  • Fentanyl
  • Fentanylum
  • N-(1-Phenethyl-4-piperidinyl)-N-phenylpropionamide
  • N-(1-Phenethyl-4-piperidyl)propionanilide
  • N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide
  • N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide
  • N-Phenethyl-4-(N-propionylanilino)piperidine
  • N-Phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide
  • Phentanyl
Thuốc giảm đau, hạ sốt, chống viêm không steroid, điều trị Gút và các bệnh xương khớp
Thuốc Gốc
Small Molecule
CAS: 437-38-7
ATC: N01AH01, N02AB03
ĐG : 4uOrtho LLC , http://www.4udr.com
CTHH: C22H28N2O
PTK: 336.4705
A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H28N2O
Phân tử khối
336.4705
Monoisotopic mass
336.220163528
InChI
InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
InChI Key
InChIKey=PJMPHNIQZUBGLI-UHFFFAOYSA-N
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
Traditional IUPAC Name
fentanyl
SMILES
CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1
Độ tan chảy
83-84
Độ hòa tan
200 mg/L (at 25 °C)
logP
4.05
logS
-4.2
pKa (Strongest Basic)
8.77
PSA
23.55 Å2
Refractivity
103.48 m3·mol-1
Polarizability
40.03 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
MDDR-Like Rule
true
Dược Lực Học : Fentanyl is an opioid analgesic. Fentanyl interacts predominately with the opioid mu-receptor but also binds to kappa and delta-type opioid receptors. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, Fentanyl exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Fentanyl may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Fentanyl depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
Cơ Chế Tác Dụng : A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078) Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Fentanyl's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hypopolarization and reduced neuronal excitability.
Dược Động Học :
▧ Absorption :
Bioavailability is 92% following transdermal administration and 50% following buccal administration.
▧ Volume of Distribution :
* 3 to 8 L/kg [Surgical Patients] * 0.8 to 8 [Hepatically Impaired Patients]
▧ Protein binding :
80-85%
▧ Metabolism :
Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system.
▧ Route of Elimination :
Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system and mostly eliminated in urine. Within 72 hours of IV fentanyl administration, approximately 75% of the dose is excreted in urine, mostly as metabolites with less than 10% representing unchanged drug.
▧ Half Life :
7 hours (range 3-12)
▧ Clearance :
* 27 – 75 L/h [Surgical Patients receving IV administration] * 3 – 80 L/h [Hepatically Impaired Patients receving IV administration] * 30 – 78 L/h [Renally Impaired Patients receving IV administration]
Độc Tính : Fentanyl has an LD50 of 3.1 milligrams per kilogram in rats, and, 0.03 milligrams per kilogram in monkeys. The LD50 in humans is not known.
Chỉ Định : For the treatment of cancer patients with severe pain that breaks through their regular narcotic therapy.
Tương Tác Thuốc :
  • Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
  • Amiodarone Possible bradycardia, hypotension
  • Amprenavir The protease inhibitor, amprenavir, may increase the effect and toxicity of fentanyl.
  • Bicalutamide CYP3A4 Inhibitors like bicalutamide may increase the serum concentration of fentanyl. The risk of prolonged adverse effects, including potentially fatal respiratory depression is increased. Consider therapy modification.
  • Cimetidine Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of fentanyl. Closely monitor changes in the therapeutic and adverse effects of fentanyl if cimetidine is initiated, discontinued or dose changed.
  • Clotrimazole CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of fentanyl. Concurrent use of fentanyl with any CYP3A4 inhibitor may result in increased fentanyl concentrations and could increase or prolong adverse effects, including potentially fatal respiratory depression. Patients receiving fentanyl and any CYP3A4 inhibitor should be closely monitored for several days following initiation of the combination, and fentanyl dosage reductions should be made as appropriate.
  • Conivaptan CYP3A4 Inhibitors (Strong) may increase the serum concentration of Fentanyl. Concurrent use of fentanyl with any CYP3A4 inhibitor may result in increased fentanyl concentrations and could increase or prolong adverse effects, including potentially fatal respiratory depression. Patients receiving fentanyl and any CYP3A4 inhibitor should be closely monitored for several days following initiation of the combination, and fentanyl dosage reductions should be made as appropriate.
  • Eltrombopag Increases levels of Fentanyl via metabolism decrease. UDP-glucuronosyltransferase inhibition.
  • Fluconazole Fluconazole may increase levels/toxicity of fentanyl.
  • Fosamprenavir The protease inhibitor, fosamprenavir, may increase the effect and toxicity of fentanyl.
  • Indinavir The protease inhibitor, indinavir, may increase the effect and toxicity of fentanyl.
  • Itraconazole Itraconazole may increase levels/toxicity of fentanyl.
  • Ketoconazole Ketoconazole may increase levels/toxicity of fentanyl.
  • Nelfinavir The protease inhibitor, nelfinavir, may increase the effect and toxicity of fentanyl.
  • Rifampicin Rifampin may decrease the serum level and therapeutic effect of fentanyl.
  • Ritonavir Ritonavir increases the effect and toxicity of fentanyl/alfentanyl
  • Rotigotine Pharmacodynamic synergism may increase the effects of rotigotine. Monitor therapy closely.
  • Saquinavir The protease inhibitor, saquinavir, may increase the effect and toxicity of fentanyl.
  • Telithromycin Telithromycin may reduce clearance of Fentanyl. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Fentanyl if Telithromycin is initiated, discontinued or dose changed.
  • Tranylcypromine Possible increased risk of serotonin syndrome.
  • Triprolidine The CNS depressants, Triprolidine and Fentanyl, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of fentanyl by decreasing its metabolism. Adverse effects include life-threatening respiratory depression. Monitor for changes in the therapeutic and adverse effects of fentanyl if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Injection, solution - Intravenous - 0.05 mg/mL
Lozenge - Oral - 200 mcg; 400 mcg; 600 mcg; 800 mcg; 1200 mcg; 1600 mcg
Patch - Transdermal
Solution - Nasal - 400 mcg/spray
Spray - Sublingual - 100 mcg; 200 mcg; 400 mcg; 600 mcg; 800 mcg
Tablet - Buccal - 100 mcg; 200 mcg; 400 mcg; 600 mcg; 800 mcg
Tablet - Sublingual - 100 mcg; 200 mcg; 300 mcg; 400 mcg; 600 mcg; 800 mcg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Abstral
  • Công ty : Cephalon
    Sản phẩm biệt dược : Actiq
  • Công ty : Janssen
    Sản phẩm biệt dược : Duragesic
  • Công ty : Janssen
    Sản phẩm biệt dược : Durogesic
  • Công ty : Pfizer
    Sản phẩm biệt dược : Fentanest
  • Công ty :
    Sản phẩm biệt dược : Lazanda
  • Công ty : Archimedes
    Sản phẩm biệt dược : Nasalfent
  • Công ty : Gedeon Richter
    Sản phẩm biệt dược : Rapinyl
  • Sản phẩm biệt dược : Subsys
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00813
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3345
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506372
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00320
ChemSpider
http://www.chemspider.com/Chemical-Structure.3228.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50008984
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0781-7240-55
PharmGKB
http://www.pharmgkb.org/drug/PA449599
Wikipedia
http://en.wikipedia.org/wiki/Fentanyl
RxList
http://www.rxlist.com/cgi/generic2/fentanyl.htm
Drugs.com
http://www.drugs.com/fentanyl.html
... loading
... loading