Tìm theo
Codeine
Các tên gọi khác (19 ) :
  • (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
  • (5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
  • 3-Methylmorphin
  • 3-methylmorphine
  • 7,8-Didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol
  • Codein
  • Codeína
  • Codéine
  • Codeine anhydrous
  • Codeinum
  • Codicept
  • Coducept
  • L-Codeine
  • Methylmorphine
  • morphine 3-methyl ether
  • Morphine monomethyl ether
  • morphine monomethyl ether
  • morphine-3-methyl ether
  • O(3)-Methylmorphine
Thuốc tác dụng trên đường hô hấp
Thuốc Gốc
Small Molecule
CAS: 76-57-3
ATC: N02AA08, R05DA04, R05DA12
ĐG : Actavis Group , http://www.actavis.com
CTHH: C18H21NO3
PTK: 299.3642
An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C18H21NO3
Phân tử khối
299.3642
Monoisotopic mass
299.152143543
InChI
InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChI Key
InChIKey=OROGSEYTTFOCAN-DNJOTXNNSA-N
IUPAC Name
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
Traditional IUPAC Name
codeine
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
Độ tan chảy
157.5 °C
Độ sôi
250 °C at 2.20E+01 mm Hg
Độ hòa tan
9000 mg/L (at 20 °C)
logP
1.19
logS
-1.52
pKa (strongest acidic)
13.78
pKa (Strongest Basic)
9.19
PSA
41.93 Å2
Refractivity
84.6 m3·mol-1
Polarizability
31.95 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
4
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
5
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
8.21 (at 25 °C)
Dược Lực Học : Codeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. It is selective for the mu receptor, but with a much weaker affinity than morphine. The analgesic properties of codeine have been speculated to come from its conversion to morphine. The principle therapeutic action is analgesia. Codeine concentrations do not correlate with brain concentration or relief of pain. The minimum effective concentration is highly variable is influenced by numerous factors, including but not limited to, age, previous opioid use, age, and general medical condition. However, the effective dose for patients that have developed tolerance is significantly higher than the opioid-naive patients.
Cơ Chế Tác Dụng : An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. [PubChem] 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. Codeine'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 hyperpolarization and reduced neuronal excitability.
Dược Động Học :
▧ Absorption :
Well absorbed following oral administration with a bioavailability of approximately 90%. Maximum plasma concentration occurs 60 minutes post-administration. Food does not effect the rate or extent of absorption of codeine.
▧ Volume of Distribution :
Apparent volume of distribution = 3-6 L/kg
▧ Protein binding :
7-25% bound to plasma proteins.
▧ Metabolism :
Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6 to morphine. 70-80% of the dose undergoes glucuronidation to form codeine-6-glucuronide. This process is mediated by UDP-glucuronosyltransferase UGT2B7 and UGT2B4. 5-10% of the dose undergoes O-demethylation to morphine and 10% undergoes N-demethylation to form norcodeine. CYP2D6 mediates the biotransformation to morphine. CYP3A4 is the enzymes that mediates the conversion to norcodiene. Morphine and norcodeine are further metabolized and undergo glucuronidation. The glucuronide metabolites of morphine are morphine-3-glucuronide (M3G) and morphine-6-glucuronide (M6G). Both morphine and morphine-6-glucuronide are active and have analgesic activity. Norcodiene and M3G do not have any analgesic properties.
▧ Route of Elimination :
90% of the total dose of codeine is excreted through the kidneys, of which 10% is unchanged codeine.
▧ Half Life :
Plasma half-lives of codeine and its metabolites have been reported to be approximately 3 hours.
Độc Tính : Respiratory depression, sedation and miosis and common symptoms of overdose. Other symptoms include nausea, vomiting, skeletal muscle flaccidity, bradycardia, hypotension, and cool, clammy skin. Apnea and death may ensue.
Chỉ Định : For treatment and management of pain (systemic). It is also used as an antidiarrheal and as a cough suppressant.
Tương Tác Thuốc :
  • Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
  • Cimetidine Cimetidine may decrease the therapeutic effect of codeine by decreasing its metabolism to its active metabolite, morphine. Monitor for changes in the therapeutic effect of codeine if cimetidine is initiated, discontinued or dose changed.
  • Dihydroquinidine barbiturate Quinidine decreases the analgesic effect of codeine
  • Quinidine Quinidine decreases the analgesic effect of codeine
  • Quinidine barbiturate Quinidine decreases the analgesic effect of codeine
  • Terbinafine Terbinafine may decrease the efficacy of Codeine by inhibiting active metabolite production. Consider an alternate analgesic or monitor for effectiveness of Codeine.
  • Triprolidine The CNS depressants, Triprolidine and Codeine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Liều Lượng & Cách Dùng : Injection, solution - Parenteral - 15 mg/mL; 30 mg/mL
Solution - Oral - 30 mg/5 mL
Tablet - Oral - 15 mg, 30 mg, 60 mg
Tablet, delayed release - Oral - 50 mg, 100 mg, 150 mg, 200 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Sigma
    Sản phẩm biệt dược : Actacode
  • Sản phẩm biệt dược : Bisoltus
  • Công ty : Qualiphar
    Sản phẩm biệt dược : Bromophar
  • Công ty : Sanofi-Aventis
    Sản phẩm biệt dược : Bronchicum
  • Công ty : Pharmacobel
    Sản phẩm biệt dược : Bronchodine
  • Công ty : Antigen
    Sản phẩm biệt dược : Codant
  • Công ty : Pierre Fabre
    Sản phẩm biệt dược : Codedrill
  • Công ty : Cristália
    Sản phẩm biệt dược : Codein
  • Công ty : Belmac
    Sản phẩm biệt dược : Codeisan
  • Sản phẩm biệt dược : Coderpina
  • Công ty : Welti
    Sản phẩm biệt dược : Codicalm
  • Công ty : Pinewood
    Sản phẩm biệt dược : Codinex
  • Công ty : Hwang's
    Sản phẩm biệt dược : Cougel
  • Công ty : Mey See
    Sản phẩm biệt dược : Coutan
  • Công ty : Center
    Sản phẩm biệt dược : Dinco
  • Công ty : Farmacom
    Sản phẩm biệt dược : Farmacod
  • Công ty : Thornton & Ross
    Sản phẩm biệt dược : Galcodine
  • Công ty : Siphat
    Sản phẩm biệt dược : Pectoral
  • Công ty : MaxMedic
    Sản phẩm biệt dược : Tussoret
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00318
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5284371
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507764
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06174
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D03580
ChemSpider
http://www.chemspider.com/Chemical-Structure.4447447.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/54868-2541-0
PharmGKB
http://www.pharmgkb.org/drug/PA449088
Wikipedia
http://en.wikipedia.org/wiki/Codeine
RxList
http://www.rxlist.com/cgi/generic/codphos.htm
Drugs.com
http://www.drugs.com/cdi/codeine-phosphate-soluble-tablets.html
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