Tìm theo
Butorphanol
Các tên gọi khác (6 ) :
  • (-)-17-(Cyclobutylmethyl)morphinan-3,14-diol
  • (-)-Butorphanol
  • (-)-N-Cyclobutylmethyl-3,14-dihydroxymorphinan
  • Butorfanol
  • Butorphanol
  • Butorphanolum
Thuốc giảm đau có opioid
Thuốc Gốc
Small Molecule
CAS: 42408-82-2
ATC: N02AF01
ĐG : Apotex Inc. , http://www.apotex.com
CTHH: C21H29NO2
PTK: 327.4605
A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C21H29NO2
Phân tử khối
327.4605
Monoisotopic mass
327.219829177
InChI
InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1
InChI Key
InChIKey=IFKLAQQSCNILHL-QHAWAJNXSA-N
IUPAC Name
(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene-4,10-diol
Traditional IUPAC Name
butorphanol
SMILES
[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1
Độ tan chảy
272-274
Độ hòa tan
Moderate
logP
3.3
logS
-3.3
pKa (strongest acidic)
9.86
pKa (Strongest Basic)
10.7
PSA
43.7 Å2
Refractivity
95.92 m3·mol-1
Polarizability
37.94 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
1
Number of Rings
5
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Butorphanol is a synthetic opioid agonist-antagonist analgesic with a pharmacological and therapeutic profile that has been well established since its launch as a parenteral formulation in 1978. The introduction of a transnasal formulation of butorphanol represents a new and noninvasive presentation of an analgesic for moderate to severe pain. This route of administration bypasses the gastrointestinal tract, and this is an advantage for a drug such as butorphanol that undergoes significant first-pass metabolism after oral administration. The onset of action and systemic bioavailability of butorphanol following transnasal delivery are similar to those after parenteral administration. Butorphanol blocks pain impulses at specific sites in the brain and spinal cord.
Cơ Chế Tác Dụng : A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain. [PubChem] The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Butorphanol is a mixed agonist-antagonist that exerts antagonistic or partially antagonistic effects at mu opiate receptor sites, but is thought to exert its agonistic effects principally at the kappa and sigma opiate receptors.
Dược Động Học :
▧ Absorption :
Rapidly absorbed after intramuscular injection and peak plasma levels are reached in 20-40 minutes. The absolute bioavailability is 60-70% and is unchanged in patients with allergic rhinitis. In patients using a nasal vasoconstrictor (oxymetazoline) the fraction of the dose absorbed was unchanged, but the rate of absorption was slowed. Oral bioavailability is only 5-17% because of extensive first-pass metabolism.
▧ Volume of Distribution :
* 305 to 901 L
▧ Protein binding :
Serum protein binding is approximately 80%.
▧ Metabolism :
Extensively metabolized in the liver. The pharmacological activity of butorphanol metabolites has not been studied in humans; in animal studies, butorphanol metabolites have demonstrated some analgesic activity.
▧ Route of Elimination :
Butorphanol is extensively metabolized in the liver. Elimination occurs by urine and fecal excretion.
▧ Half Life :
The elimination half-life of butorphanol is about 18 hours. In renally impaired patients with creatinine clearances <30 mL/min the elimination half-life is approximately doubled. After intravenous administration to patients with hepatic impairment, the elimination half-life of butorphanol was approximately tripled.
▧ Clearance :
* 99 +/- 23 L/h [Young with IV 2 mg] * 82 +/- 21 [Eldery with IV 2 mg]
Độc Tính : The clinical manifestations of butorphanol overdose are those of opioid drugs in general. The most serious symptoms are hypoventilation, cardiovascular insufficiency, coma, and death.
Chỉ Định : For the relief of moderate to severe pain.
Tương Tác Thuốc :
  • Alvimopan Opioid analgesics such as butorphanol may enhance the adverse/toxic effect of alvimopan. This is most notable for patients receiving long-term (i.e., more than 7 days) opiates prior to alvimopan initiation. According to alvimopan prescribing information, alvimopan is contraindicated in patients receiving therapeutic doses of opioids for more than 7 consecutive days immediately prior to alvimopan initiation. Monitor for increased alvimopan adverse effects in patients using opioids prior to alvimopan.
  • Droperidol Droperidol may enhance the CNS depressant effect of butorphanol. Consider dose reductions of droperidol or of other CNS agents (e.g., opioids, barbiturates) with concomitant use.
  • Triprolidine The CNS depressants, Triprolidine and Butorphanol, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Liều Lượng & Cách Dùng : Liquid - Nasal
Spray - Nasal
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00611
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6916249
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507553
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00837
ChemSpider
http://www.chemspider.com/Chemical-Structure.4514667.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240437
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-9639-43
PharmGKB
http://www.pharmgkb.org/drug/PA164745398
Wikipedia
http://en.wikipedia.org/wiki/Butorphanol
RxList
http://www.rxlist.com/cgi/generic2/butor.htm
Drugs.com
http://www.drugs.com/cdi/butorphanol-solution.html
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