Tìm theo
Bezitramide
Các tên gọi khác (1) :
  • 1-[1-(3-Cyano-3,3-diphenylpropyl)-4-piperidinyl]-1,3-dihydro-3-(1-oxopropyl)-2H-benzimidazol-2-one
analgesics
Thuốc Gốc
Small Molecule
CAS: 15301-48-1
ATC: N02AC05
CTHH: C31H32N4O2
PTK: 492.6114
Bezitramide is a narcotic analgesic which was discovered in 1961, clinically tested around the 1970's [1], and marketed under the name Burgodin(R). After cases of fatal overdose in the Netherlands in 2004 the drug was withdrawn from the market. In the United States Bezitramide was never been approved for clinical use. It is presently an illegal substance classified under Schedule II of the Controlled Substances Act. [wiki]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C31H32N4O2
Phân tử khối
492.6114
Monoisotopic mass
492.252526288
InChI
InChI=1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3
InChI Key
InChIKey=FLKWNFFCSSJANB-UHFFFAOYSA-N
IUPAC Name
4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
Traditional IUPAC Name
bezitramide
SMILES
CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12
Độ tan chảy
145-149 °C
Độ hòa tan
Poor water solubility
logP
4.80
logS
-4.9
pKa (Strongest Basic)
8.32
PSA
67.65 Å2
Refractivity
155.25 m3·mol-1
Polarizability
55.58 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
4
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
5
Bioavailability
1
Rule of Five
true
MDDR-Like Rule
true
Dược Lực Học : Bezitramide acts in the body to relieve pain with a potency 20 times that of methadone [1]. Its duration of action is relatively long, lasting up to 12 hours post oral administration, after the achievement of steady state. Its onset of action is slow, with a peak in analgesic effect noted between 2.5-3.5 hours after dosing. It is noted to illicit a strong antitussive effect, which could be of benefit to patients with bronchial carcinoma.
Dược Động Học :
▧ Absorption :
Bezitramide has poor water solubility, thus administration is restricted to the oral route. [1]
▧ Metabolism :
Bezitramide is a prodrug which undergoes rapid hydrolysis of a proprionyl-group to form the major metabolite, R-4618. R-4618 has analgesic properties similar to the parent compound.[1] Metabolism occurs in the gastrointestinal tract under both acidic and alkaline conditions [1].
▧ Route of Elimination :
Less than 0.3% of the dose was excreted unchanged in the urine. High concentrations in feces suggested incomplete absorption of biliary excretion. Experiments in rats demonstrated extensive (up to 70%) biliary excretion, and less than 3% urinary excretion. [1]
▧ Half Life :
11-24h. [1]
Chỉ Định : A narcotic analgesic once used for the treatment of severe chronic pain. [1]
Dữ Kiện Thương Mại
Nhà Sản Xuất
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01459
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=61791
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505037
ChemSpider
http://www.chemspider.com/Chemical-Structure.55675.html
Wikipedia
http://en.wikipedia.org/wiki/Bezitramide
... loading
... loading