Tìm theo
Cocaine
Các tên gọi khác (16 ) :
  • (-)-Cocaine
  • (−)-cocaine
  • [1R-(Exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester
  • 2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylate benzoate (ester)
  • Benzoylmethylecgonine
  • beta-Cocain
  • Cocain
  • Cocaina
  • Cocaine
  • Cocainum
  • Kokain
  • L-Cocain
  • L-Cocaine
  • Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
  • Methyl benzoylecgonine
  • Neurocaine
Thuốc tim mạch
Thuốc Gốc
Small Molecule
CAS: 50-36-2
ATC: N01BC01, R02AD03, S01HA01, S02DA02
ĐG : Cody Laboratories Inc. , http://www.codylabs.com
CTHH: C17H21NO4
PTK: 303.3529
An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H21NO4
Phân tử khối
303.3529
Monoisotopic mass
303.147058165
InChI
InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
InChI Key
InChIKey=ZPUCINDJVBIVPJ-LJISPDSOSA-N
IUPAC Name
methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Traditional IUPAC Name
cocaine
SMILES
[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C
Độ tan chảy
98 °C
Độ hòa tan
1800 mg/L (at 22 °C)
logP
2.30
logS
-2.23
pKa (Strongest Basic)
8.85
PSA
55.84 Å2
Refractivity
81.16 m3·mol-1
Polarizability
32.36 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
3
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
8.61 (at 15 °C)
Dược Lực Học : Cocaine is a local anesthetic indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
Cơ Chế Tác Dụng : An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake. [PubChem] Cocaine produces anesthesia by inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. This is achieved by reversibly binding to and inactivating sodium channels. Sodium influx through these channels is necessary for the depolarization of nerve cell membranes and subsequent propagation of impulses along the course of the nerve. Cocaine is the only local anesthetic with vasoconstrictive properties. This is a result of its blockade of norepinephrine reuptake in the autonomic nervous system. Cocaine binds differentially to the dopamine, serotonin, and norepinephrine transport proteins and directly prevents the re-uptake of dopamine, serotonin, and norepinephrine into pre-synaptic neurons. Its effect on dopamine levels is most responsible for the addictive property of cocaine.
Dược Động Học :
▧ Absorption :
Cocaine is absorbed from all sites of application, including mucous membranes and gastrointestinal mucosa. By oral or intra-nasal route, 60 to 80% of cocaine is absorbed.
▧ Metabolism :
Hepatic. Cocaine is metabolized to benzoylecgonine and ecgonine methyl ester, which are both excreted in the urine. In the presence of alcohol, a further active metabolite, cocaethylene is formed, and is more toxic then cocaine itself.
▧ Half Life :
1 hour
Độc Tính : Intense agitation, convulsions, hypertension, rhythm disturbance, coronary insufficiency, hyperthermia, rhabdomyolysis, and renal impairment. Oral mouse LD50 = 96 mg/kg
Chỉ Định : For the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
Tương Tác Thuốc :
  • Atomoxetine CYP2D6 Inhibitors (Strong) such as cocaine may increase the serum concentration of atomoxetine. Initiate atomoxetine at a reduced dose (patients up to 70kg: 0.5mg/kg/day; patients 70kg or more: 40mg/day) in patients receiving a strong CYP2D6 inhibitor. The dose should only be increased to usual doses if symptoms fail to improve after 4 weeks. Patients established on atomoxetine therapy may require dosage reductions and should be monitored for increased levels/adverse effects with initiation/dose increase of a strong CYP2D6 inhibitor.
  • Disulfiram Increases the cardiac toxicity of cocaine
  • Iloperidone CYP2D6 Inhibitors (Strong) such as cocaine may increase serum concentrations of the active metabolite(s) of Iloperidone. Specifically, concentrations of the metabolite P88 may be increased. CYP2D6 Inhibitors (Strong) may decrease serum concentrations of the active metabolite(s) of Iloperidone. Specifically, concentrations of the metabolite P95 may be decreased. CYP2D6 Inhibitors (Strong) may increase the serum concentration of Iloperidone. Reduce iloperidone dose by half when administered with a strong CYP2D6 inhibitor.
  • Iobenguane Sympathomimetic that increase chances of producing a false negative imaging result
  • Tamoxifen Cocaine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Tamsulosin Cocaine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Cocaine is initiated, discontinued, or dose changed.
  • Telithromycin Telithromycin may reduce clearance of Cocaine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Cocaine if Telithromycin is initiated, discontinued or dose changed.
  • Tetrabenazine CYP2D6 Inhibitors (Strong) such as cocaine may increase the serum concentration of tetrabenazine. Specifically, concentrations of the active alpha- and beta-dihydrotetrabenazine metabolites may be increased. Patients receiving a strong inhibitor of CYP2D6 together with tetrabenazine should not exceed 50mg of tetrabenazine. Also, patients already taking tetrabenazine prior to starting a strong CYP2D6 inhibitor should have their tetrabenazine dose reduced by 50% upon initiation of the strong CYP2D6 inhibitor.
  • Tolterodine Cocaine may decrease the metabolism and clearance of Tolterodine. Monitor for adverse/toxic effects of Tolterodine.
  • Tramadol Cocaine may decrease the effect of Tramadol by decreasing active metabolite production.
  • Trimipramine The strong CYP2D6 inhibitor, Cocaine, may decrease the metabolism and clearance of Trimipramine, a CYP2D6 substrate.
  • Venlafaxine Cocaine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Cocaine is initiated, discontinued, or dose changed.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of cocaine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cocaine if voriconazole is initiated, discontinued or dose changed.
  • Zuclopenthixol Cocaine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if cocaine is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Liquid - Topical
Dữ Kiện Thương Mại
Giá thị trường
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00907
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C01416
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00110
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50006232
PharmGKB
http://www.pharmgkb.org/drug/PA449072
Wikipedia
http://en.wikipedia.org/wiki/Cocaine
RxList
http://www.rxlist.com/cgi/generic/cocaine.htm
Drugs.com
http://www.drugs.com/cons/cocaine-hydrochloride-topical.html
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