 Home > Encyclopedia > DL-Amethopterin

DL-Amethopterin

DL-Amethopterin structure

CAS No:
60388-53-6
Formula:
C20H22N8O5
Chemical Name:
DL-Amethopterin
Synonyms:
Glutamic acid,N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-;DL-Glutamic acid,N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-;N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]glutamic acid;DL-Methotrexate;DL-Amethopterin;NSC 117356;(±)-Methotrexate;2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid;184883-35-0
Categories:
Dyes and Pigments > Pigment

Description

yellow to orange crystalline powder

2-[[[4-[(2,4-diamino-6-pteridinyl)methyl-methylamino]phenyl]-oxomethyl]amino]pentanedioic acid is a member of folic acids.|An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of TETRAHYDROFOLATE DEHYDROGENASE and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA.

DL-Amethopterin Basic Attributes

Molecular Weight：

454.44

Exact Mass：

454.44

EC Number：

262-213-7

NSC Number：

757113|117356

Characteristics

PSA：

210.54000

XLogP3：

1.82170

Appearance：

yellow powder

Density：

1.536 g/cm3

Melting Point：

195 °C (dec.)(lit.)

Water Solubility：

H2O: Add a minimal amount of 0.1燦 NaOH to solubilize, then dilute in neutral buffer or saline. Diluted stock is stable for 1爓eek refrigerated and for 1爉onth frozen at?#8722;20?#x00b0;C.insoluble

Storage Conditions：

−20°C

Vapor Pressure：

2.1X10-19 mm Hg at 25 deg C /Estimated/

Safety Information

Transport codes：

UN 1544 6.1/PG 2

wgk germany：

hazard class code：

61-25-36/38-23/24/25

safety instructions：

53-26-36/37-45-36/37/39

RTECS Number：

MA1224100

Marks：

Drug Information

MeSH：

Non-steroidal chemical compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Nonsteroidal.)|Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)|Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)|Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)|Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

MeSH Entry Terms：

Amethopterin

DL-Amethopterin Use and Manufacturing

Uses

Racemic Methotrexate (M260675), a folic acid antagonist. Used as a antineoplastic and antirheumatic.

Manufacturing Info：

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

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:454.4
XLogP3:-1.8
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:9
Exact Mass:454.17131583
Monoisotopic Mass:454.17131583
Topological Polar Surface Area:211
Heavy Atom Count:33
Complexity:704
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes