Tìm theo
Epirubicin
Các tên gọi khác (9 ) :
  • 4'-Epiadriamycin
  • Epiadriamycin
  • Epirubicin
  • Epirubicina
  • Epirubicine
  • Epirubicinum
  • Pidorubicina
  • Pidorubicine
  • Pidorubicinum
Thuốc chống ung thư và tác động vào hệ thống miễn dịch
Thuốc Gốc
Small Molecule
CAS: 56420-45-2
ATC: L01DB03
ĐG : APP Pharmaceuticals , http://www.apppharma.com
CTHH: C27H29NO11
PTK: 543.5193
An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
543.5193
Monoisotopic mass
543.174060775
InChI
InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1
InChI Key
InChIKey=AOJJSUZBOXZQNB-VTZDEGQISA-N
IUPAC Name
(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
Traditional IUPAC Name
epirubicin
SMILES
COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[[email protected]](O)(C[[email protected]@H]3O[[email protected]]3C[[email protected]](N)[[email protected]@H](O)[[email protected]](C)O3)C(=O)CO)C(O)=C1C2=O
Độ tan chảy
344.53 °C
Độ hòa tan
0.093 mg/ml
logP
-0.5
logS
-2.7
pKa (strongest acidic)
9.53
pKa (Strongest Basic)
8.94
PSA
206.07 Å2
Refractivity
134.59 m3·mol-1
Polarizability
53.88 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
12
H Bond Donor Count
6
Physiological Charge
1
Number of Rings
5
Bioavailability
0
Dược Lực Học : Epirubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Epirubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Epirubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Cơ Chế Tác Dụng : An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA. [PubChem] Epirubicin has antimitotic and cytotoxic activity. It inhibits nucleic acid (DNA and RNA) and protein synthesis through a number of proposed mechanisms of action: Epirubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. It also interferes with DNA replication and transcription by inhibiting DNA helicase activity.
Dược Động Học :
▧ Absorption :
100%
▧ Volume of Distribution :
* 21 ± 2 L/kg [60 mg/m2 Dose] * 27 ± 11 L/kg [75 mg/m2 Dose] * 23 ± 7 L/kg [120 mg/m2 Dose] * 21 ± 7 L/kg [150 mg/m2 Dose]
▧ Protein binding :
77%
▧ Metabolism :
Extensively and rapidly metabolized in the liver. Epirubicin is also metabolized by other organs and cells, including red blood cells. The four main metabolic routes are: (1) reduction of the C-13 keto-group with the formation of the 13(S)-dihydro derivative, epirubicinol; (2) conjugation of both the unchanged drug and epirubicinol with glucuronic acid; (3) loss of the amino sugar moiety through a hydrolytic process with the formation of the doxorubicin and doxorubicinol aglycones; and (4) loss of the amino sugar moiety through a redox process with the formation of the 7-deoxy-doxorubicin aglycone and 7-deoxy-doxorubicinol aglycone. Epirubicinol exhibits in vitro cytoxic activity (~10% that of epirubicin), but it is unlikely to reach sufficient concentrations in vivo to produce cytotoxic effects.
▧ Route of Elimination :
Epirubicin and its major metabolites are eliminated through biliary excretion and, to a lesser extent, by urinary excretion.
▧ Half Life :
Half-lives for the alpha, beta, and gamma phases of about 3 minutes, 2.5 hours and 33 hours, respectively
▧ Clearance :
* 65 +/- 8 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 60 mg/m2] * 83 +/- 14 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 75 mg/m2] * 65 +/- 13 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 120 mg/m2] * 69 +/- 13 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 150 mg/m2]
Độc Tính : bone marrow aplasia, grade 4 mucositis, and gastrointestinal bleeding
Chỉ Định : For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer.
Tương Tác Thuốc :
  • Cimetidine Cimetidine can increase epirubicin levels
  • Trastuzumab Trastuzumab may increase the cardiotoxicity of Epirubicin. Signs and symptoms of cardiac dysfunction should be monitored for frequently. Increased risk of heart failure. Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Liều Lượng & Cách Dùng : Solution - Intravenous - 200 mg/100 ml
Solution - Intravenous - 50 mg/25 ml
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Pfizer
    Sản phẩm biệt dược : Ellence
  • Công ty :
    Sản phẩm biệt dược : Epirubicin Ebewe
  • Công ty :
    Sản phẩm biệt dược : Pharmorubicin
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