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Aminopterin

Aminopterin structure

CAS No:
54-62-6
Formula:
C19H20N8O5
Chemical Name:
Aminopterin
Synonyms:
L-Glutamic acid,N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-;Glutamic acid,N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-,L-;N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid;NSC 739;Aminopterin;4-Aminopteroylglutamic acid;Aminopterine;4-Aminofolic acid;APGA;Pteramina;(2S)-2-[[4-[(2,4-Diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid;120382-78-7;64801-55-4
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Aminopterin (4-Aminofolic acid), the 4-amino derivative of folic acid, is a folic acid antagonist. Aminopterin catalyses the reduction of folic acid to tetrahydrofolic acid, and competitively inhibits dihydrofolate reductase (DHFR) with a Ki of 3.7 pM. Aminopterin has anticancer and immunosuppressive activity. Aminopterin is used in treatment of pediatric leukemia[1][2].

Solid

Aminopterin Basic Attributes

Molecular Weight：

440.41

Exact Mass：

440.41

EC Number：

200-209-9

NSC Number：

757427|739

DSSTox ID：

DTXSID50873145

HScode：

2933990090

Characteristics

PSA：

219.33000

XLogP3：

-1.21

Appearance：

yellow powder

Density：

1.6±0.1 g/cm3

Melting Point：

228-235 °C (dec.)

Flash Point：

87℃

Refractive Index：

1.762

Water Solubility：

2 M NaOH: 50 mg/mL

Storage Conditions：

2-8°C

Vapor Pressure：

2.3X10-19 mg Hg at 25 °C /Estimated/

Toxicity：

Oral-ratLDL0: 2.5 mg/kg; Oral-Mouse LD50: 3 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

Specific rotation：

18 º (c=1% in 0.1N NaOH)

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

UN 2811 6.1/PG 1

wgk germany：

hazard class code：

61-28-63-26/27/28

safety instructions：

53-28-36/37-45-36/37/39-22

RTECS Number：

MA1050000

Marks：

T+

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P201-P264-P301 + P310-P308 + P313

Hazard Statements：

H300-H360

Toxicity

Toxicity class：

most toxic

Aminopterin Use and Manufacturing

Uses

antineoplastic, antirheumatic, folic acid antagonist

Manufacturing Info：

L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-: ACTIVE

Computed Properties

Molecular Weight:440.4
XLogP3:-2
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:9
Exact Mass:440.15566577
Monoisotopic Mass:440.15566577
Topological Polar Surface Area:219
Heavy Atom Count:32
Complexity:674
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes