Tìm theo
Aminopterin
Các tên gọi khác (13 ) :
  • 4-amino-4-deoxypteroylglutamate
  • 4-amino-PGA
  • 4-aminofolic acid
  • 4-aminopteroylglutamic acid
  • 4'-Amino-folsaeure
  • A-ninopterin
  • A-Ninopterin
  • Aminopteridine
  • Aminopterine
  • APGA
  • Minopterin
  • N-(4-{[(2,4-Diamino-6-pteridinyl)methyl]amino}benzoyl)glutamic acid
  • Pteramina
folic acid antagonists
Thuốc Gốc
Small Molecule
CAS: 54-62-6
CTHH: C19H20N8O5
PTK: 440.4127
Aminopterin is an amino derivative of folic acid, which was once used as an antineoplastic agent in the treatment of pediatric leukemia. In the 1950's its production was discontinued in favor of methotrexate, which is less potent but less toxic. Off label, aminopterin has also been used in the treatment of psoriasis. Clinicians need to be aware of the characteristic teratologic effects of aminopterin and methotrexate.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C19H20N8O5
Phân tử khối
440.4127
Monoisotopic mass
440.15566579
InChI
InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
InChI Key
InChIKey=TVZGACDUOSZQKY-LBPRGKRZSA-N
IUPAC Name
(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name
4-aminopteroylglutamic acid
SMILES
NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=N2)C(N)=N1
Độ tan chảy
225 °C (437 °F)
Độ hòa tan
3.0X103 mg/L
logP
-1.8
logS
-3.6
pKa (strongest acidic)
3.38
pKa (Strongest Basic)
2.25
PSA
219.33 Å2
Refractivity
114.98 m3·mol-1
Polarizability
44.14 Å3
Rotatable Bond Count
9
H Bond Acceptor Count
12
H Bond Donor Count
6
Physiological Charge
-2
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
pKa
5.5
Cơ Chế Tác Dụng : Aminopterin is an amino derivative of folic acid, which was once used as an antineoplastic agent in the treatment of pediatric leukemia. In the 1950's its production was discontinued in favor of methotrexate, which is less potent but less toxic. Off label, aminopterin has also been used in the treatment of psoriasis. Clinicians need to be aware of the characteristic teratologic effects of aminopterin and methotrexate. Aminopterin is an amino derivative of folic acid which binds competitively to the dihydrofolate reductase enzyme to block tetrahydrofolate synthesis. Tetrahydrofolate is essential in the production of purines and pyrimadines, thus it's deficiency results in a reduction of DNA, RNA and protein synthesis.
Chỉ Định : Prior to its withdrawal, aminopterin was initially used in the treatment of childhood leukemia; specifically to induce remissions. Later, aminopterin was used off-label in the United States to treat psoriasis, yielding dramatic lesion clearing. Aminopterin was later supplanted by methotrexate for treating cancer because of its better therapeutic index. Aminopterin (as well as methotrexate) has also been explored for use as an abortifacient. However, their association with severe congenital malformations and teratogenic effects have become known as fetal aminopterin syndrome.
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB08878
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02527
Wikipedia
http://en.wikipedia.org/wiki/Aminopterin
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