Tìm theo
Mechlorethamine
Các tên gọi khác (13 ) :
  • 2,2'-dichloro-N-methyldiethylamine
  • beta,Beta'-dichlorodiethyl-N-methylamine
  • Bis(2-chloroethyl)methylamine
  • Bis(beta-chloroethyl)methylamine
  • Chlormethine
  • Mechlorethamine
  • Methylbis(2-chloroethyl)amine
  • Methylbis(beta-chloroethyl)amine
  • Mustine
  • N-methyl-bis(2-chloroethyl)amine
  • N-Methyl-bis(beta-chloroethyl)amine
  • Nitrogen mustard
  • β,β'-dichlorodiethyl-N-methylamine
Thuốc điều trị ung thư
Thuốc Gốc
Small Molecule
CAS: 51-75-2
ATC: L01AA05, D08AX04
ĐG : Lundbeck Inc. , http://www.lundbeckinc.com
CTHH: C5H11Cl2N
PTK: 156.054
A vesicant and necrotizing irritant destructive to mucous membranes, mechlorethamine is an alkylating drug. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem] The FDA granted marketing approval for the orphan drug Valchlor (mechlorethamine) gel on August 23, 2013 for the topical treatment of stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma (CTCL) in patients who have received prior skin-directed therapy. Each tube of Valchlor contains 0.016% of mechlorethamine which is equivalent to 0.02% mechlorethamine HCL.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C5H11Cl2N
Phân tử khối
156.054
Monoisotopic mass
155.026854771
InChI
InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
InChI Key
InChIKey=HAWPXGHAZFHHAD-UHFFFAOYSA-N
IUPAC Name
bis(2-chloroethyl)(methyl)amine
Traditional IUPAC Name
mechlorethamine
SMILES
CN(CCCl)CCCl
Độ tan chảy
108 - 110°C
Độ sôi
87°C at 1.80E+01 mm Hg
Độ hòa tan
Very soluble
logP
0.91
logS
-0.67
pKa (Strongest Basic)
6.08
PSA
3.24 Å2
Refractivity
38.67 m3·mol-1
Polarizability
15.84 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
1
H Bond Donor Count
0
Physiological Charge
0
Number of Rings
0
Bioavailability
1
Rule of Five
true
pKa
6.43 (at 25°C)
Dược Lực Học : Mechlorethamine also known as mustine, nitrogen mustard, and HN2, is the prototype anticancer chemotherapeutic drug. Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an analogue of mustard gas and was derived from toxic gas warfare research. It belongs to the group of nitrogen mustard alkylating agents. 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 : A vesicant and necrotizing irritant destructive to mucous membranes, mechlorethamine is an alkylating drug. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem] The FDA granted marketing approval for the orphan drug Valchlor (mechlorethamine) gel on August 23, 2013 for the topical treatment of stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma (CTCL) in patients who have received prior skin-directed therapy. Each tube of Valchlor contains 0.016% of mechlorethamine which is equivalent to 0.02% mechlorethamine HCL. Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, 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. Mechlorethamine is cell cycle phase-nonspecific.
Dược Động Học :
▧ Absorption :
Partially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids. When it is topically administered, systemic exposure was undetectable.
▧ Metabolism :
Undergoes rapid chemical transformation and combines with water or reactive compounds of cells, so that the drug is no longer present in active form a few minutes after administration.
▧ Half Life :
15 minutes
Độc Tính : Symptoms of overexposure include severe leukopenia, anemia, thrombocytopenia, and a hemorrhagic diathesis with subsequent delayed bleeding may develop. Death may follow. The most common adverse reactions (≥5%) of the topical formulation are dermatitis, pruritus, bacterial skin infection, skin ulceration or blistering, and hyperpigmentation. The oral LD50 for a rat is 10 mg/kg.
Chỉ Định : For the palliative treatment of Hodgkin's disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Also for the palliative treatment of metastatic carcinoma resulting in effusion.
Tương Tác Thuốc :
  • Bendamustine Increases toxicity through pharmacodynamic synergism. Additive myelosuppression.
  • Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Liều Lượng & Cách Dùng : Gel - Topical - 0.016%
Injection, powder, for solution - Intravenous - 10 mg
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Mustargen 10 mg vial
    Giá bán buôn : USD >178.71
    Đơn vị tính : vial
Nhà Sản Xuất
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00888
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4033
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505784
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07115
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D07671
ChemSpider
http://www.chemspider.com/Chemical-Structure.3893.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/66215-016-60
PharmGKB
http://www.pharmgkb.org/drug/PA450336
Wikipedia
http://en.wikipedia.org/wiki/Mechlorethamine
RxList
http://www.rxlist.com/cgi/generic3/mustargen.htm
Drugs.com
http://www.drugs.com/cdi/mechlorethamine.html
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