Tìm theo
Melphalan
Các tên gọi khác (16 ) :
  • 3-(P-(Bis(2-chloroethyl)amino)phenyl)-L-alanine
  • 3-P-(Di(2-chloroethyl)amino)-phenyl-L-alanine
  • 4-(Bis(2-chloroethyl)amino)-L-phenylalanine
  • L-3-(P-(Bis(2-chloroethyl)amino)phenyl)alanine
  • L-PAM
  • L-Phenylalanine mustard
  • L-Sarcolysine
  • Melfalano
  • Melphalanum
  • p-Bis(beta-chloroethyl)aminophenylalanine
  • P-Di-(2-chloroethyl)amino-L-phenylalanine
  • P-L-Sarcolysin
  • P-N-Bis(2-chloroethyl)amino-L-phenylalanine
  • p-N,N-bis(2-chloroethyl)amino-L-phenylalanine
  • Phenylalanine mustard
  • Phenylalanine nitrogen mustard
Thuốc Gốc
Small Molecule
CAS: 148-82-3
ATC: L01AA03
ĐG : Antibioticos Ltd.
CTHH: C13H18Cl2N2O2
PTK: 305.2
An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - melphalan, the racemic mixture - merphalan, and the dextro isomer - medphalan; toxic to bone marrow, but little vesicant action; potential carcinogen. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C13H18Cl2N2O2
Phân tử khối
305.2
Monoisotopic mass
304.074533244
InChI
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
InChI Key
InChIKey=SGDBTWWWUNNDEQ-LBPRGKRZSA-N
IUPAC Name
(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
Traditional IUPAC Name
melphalan
SMILES
N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O
Độ tan chảy
182.5 °C
Độ hòa tan
< 0.1 g/100 mL at 22 °C
logP
-0.52
logS
-2.9
pKa (strongest acidic)
1.29
pKa (Strongest Basic)
9.51
PSA
66.56 Å2
Refractivity
78.23 m3·mol-1
Polarizability
31.38 Å3
Rotatable Bond Count
8
H Bond Acceptor Count
4
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Melphalan is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
Cơ Chế Tác Dụng : An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - melphalan, the racemic mixture - merphalan, and the dextro isomer - medphalan; toxic to bone marrow, but little vesicant action; potential carcinogen. [PubChem] Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases (primarily at the N-7 position of guanine and to a lesser extent, at the N-3 position of adenine), forming monoadducts and resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations.
Dược Động Học :
▧ Absorption :
Incomplete, variable, 25-89% post oral dose
▧ Volume of Distribution :
* 0.5 L/kg
▧ Protein binding :
Moderate to high (60 to 90%), primarily to albumin and, to a lesser extent, alpha 1-acid glycoprotein. 30% is irreversibly bound.
▧ Metabolism :
Melphalan is not actively metabolised, it spontaneously degrades to mono and dihydroxy products.
▧ Route of Elimination :
The 24-hour urinary excretion of parent drug in these patients was 10% ± 4.5%, suggesting that renal clearance is not a major route of elimination of parent drug.
▧ Half Life :
1.5 (±0.83) hours
Độc Tính : Vomiting, ulceration of the mouth, diarrhea, and hemorrhage of the gastrointestinal tract; The principal toxic effect is bone marrow suppression. LD50=11.2 mg/kg (orally in rat)
Chỉ Định : For the palliative treatment of multiple myeloma and for the palliation of non-resectable epithelial carcinoma of the ovary. Has also been used alone or as part of various chemotherapeutic regimens as an adjunct to surgery in the treatment of breast cancer, alone or in combination regimens for palliative treatment of locally recurrent or unresectable in-transit metastatic melanoma of the extremities, as well as for the treatment of amyloidosis with prednisone.
Tương Tác Thuốc :
  • Bendamustine Increases toxicity through pharmacodynamic synergism. Additive myelosuppression.
  • Cyclosporine Melphalan increases toxicity of cyclosporine
  • Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Alkeran 2 mg tablet
    Giá bán buôn : USD >5.65
    Đơn vị tính : tablet
  • Biệt dược thương mại : Melphalan hcl 50 mg vial
    Giá bán buôn : USD >1845.6
    Đơn vị tính : vial
  • Biệt dược thương mại : Alkeran 50 mg vial
    Giá bán buôn : USD >1971.72
    Đơn vị tính : vial
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Alkeran
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01042
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00369
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50038356
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0173-0045-35
PharmGKB
http://www.pharmgkb.org/drug/PA450354
Wikipedia
http://en.wikipedia.org/wiki/Melphalan
RxList
http://www.rxlist.com/cgi/generic2/melph.htm
Drugs.com
http://www.drugs.com/cdi/melphalan.html
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