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Home> CAS DataBase Listed 5 > CAS 59-05-2
Identification of 59-05-2
  • Name:
  • L-Glutamicacid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]- (Related Reference)
  • EINECS:
  • 200-413-8
  • Synonyms:
  • Glutamicacid, N-[p-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, L-(+)-(8CI); (+)-Amethopterin; Amethopterin; Amethopterine; Antifolan; CL 14377; EMT 25299; Emtexate; Emthexate PF; L-Amethopterin; L-Methotrexate; Ledertrexate; Metatrexan; Mexate; N-[p-[[2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(+)-glutamicacid; NSC 740; R 9985; Rheumatrex; Trexall;
  • InChI:
  • InChI=1/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m1/s1
  • This structure is also available as a 2d Mol file
Safety Data of 59-05-2 Properties of 59-05-2
  • Appearance:
  • yellow crystalline powder
  • Molecular Weight:
  • 454.44
  • Density:
  • 1.536 g/cm3
  • Melting Point:
  • 195℃
  • Storage Temperature:
  • ?20°C
  • Solubility:
  • Insoluble. <0.1 g/100 mL at 19 °C
  • Biological Activity:
  • Cytotoxic agent. Inhibits thymidylate synthetase and de novo purine synthesis. Potent folic acid antagonist; inhibits dihydrofolate reductase. Also inhibits Ras carboxyl methylation in DKOB8 cells, leading to decreased p44 and Akt activation.
  • Stability:
  • Stable, but light sensitive and hygroscopic. Incompatible with strong acids, strong oxidizing agents. Store at -15C or below.
  • Usage:
  • Used as a antineoplastic and antirheumatic. A folic Acid antagonist

  • More>>

CAS No. 59-05-2 (L-Glutamicacid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]- )

  • CAS No:59-05-2
  • Molecular Weight: 454.44
  • Molecular Formula: C20H22N8O5
Properties Safety and Handling MSDS NMR Spectrum Synthesis Route Precursor and Product
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Precursor and Product
References of L-Glutamicacid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]- cas 59-05-2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 100mg/kg/4H (100mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: OTHER CHANGES
Cancer Vol. 33, Pg. 1151, 1974.
child TDLo oral 2mg/kg/12D (2mg/kg) LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
JAMA, Journal of the American Medical Association. Vol. 209, Pg. 1861, 1969.
human TDLo intramuscular 35mg/kg/28W (35mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
British Medical Journal. Vol. 2, Pg. 156, 1970.
human TDLo intramuscular 200mg/kg/5Y (200mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" Archives of Dermatology. Vol. 100, Pg. 531, 1969.
human TDLo intravenous 4650ug/kg/4W- (4.65mg/kg) LIVER: FATTY LIVER DEGERATION

LIVER: LIVER FUNCTION TESTS IMPAIRED
Proceedings of the American Association for Cancer Research. Vol. 5, Pg. 26, 1964.
human TDLo intravenous 7143ug/kg (7.143mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: CHANGES IN PLATELET COUNT

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 673, 1992.
human TDLo oral 43mg/kg/5Y (43mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: OTHER CHANGES
Archives of Dermatology. Vol. 100, Pg. 523, 1969.
man TDLo intramuscular 214ug/kg/12D- (0.214mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Clinical and Experimental Rheumatology. Vol. 14, Pg. 450, 1996.
man TDLo intravenous 740mg/kg (740mg/kg) GASTROINTESTINAL: OTHER CHANGES Archives of Internal Medicine. Vol. 136, Pg. 1321, 1976.
man TDLo oral 643ug/kg/6W-I (0.643mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Rheumatology. Vol. 14, Pg. 74, 1987.
man TDLo oral 4286ug/kg/2.7 (4.286mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION

BLOOD: APLASTIC ANEMIA
Clinical Rheumatology. Vol. 12, Pg. 535, 1993.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg) ? Anatomical Record. Vol. 178, Pg. 465, 1974.
mouse LD50 intravenous 65mg/kg (65mg/kg) ? Drugs in Japan Vol. 6, Pg. 841, 1982.
mouse LD50 oral 146mg/kg (146mg/kg) ? Drugs in Japan Vol. 6, Pg. 841, 1982.
mouse LD50 subcutaneous 250mg/kg (250mg/kg) ? National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 unreported 69mg/kg (69mg/kg) ? Cancer Research. Vol. 46, Pg. 2703, 1986.
Link to PubMed
rat LD50 intraperitoneal 6mg/kg (6mg/kg) ? Drugs in Japan Vol. 6, Pg. 841, 1982.
rat LD50 intravenous 14mg/kg (14mg/kg) ? Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.
Link to PubMed
rat LD50 oral 135mg/kg (135mg/kg) ? Drugs in Japan Vol. 6, Pg. 841, 1982.
rat LD50 subcutaneous 58mg/kg (58mg/kg) ? Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 93, 1992.
rat LD50 unreported 133ug/kg (0.133mg/kg) ? United States Patent Document. Vol. #4746662,
women LDLo intraspinal 36mg/kg/15D (36mg/kg) SPINAL CORD: OTHER DEGENERATIVE CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING
New England Journal of Medicine. Vol. 289, Pg. 770, 1973.
women TDLo oral 800ug/kg/4D-I (0.8mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA

BLOOD: OXIDANT RELATED (GPD DEFICIENT) ANEMIA
Medical Journal of Australia. Vol. 155, Pg. 493, 1991.
women TDLo oral 2mg/kg/17W-I (2mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: LEUKOPENIA
Journal of Rheumatology. Vol. 14, Pg. 74, 1987.
women TDLo parenteral 2600ug/kg (2.6mg/kg) BRAIN AND COVERINGS: CHANGES IN CEREBRAL SPINAL FLUID

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Cancer Vol. 38, Pg. 1529, 1976.
women TDLo unreported 11400ug/kg/44 (11.4mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" Clinical and Experimental Rheumatology. Vol. 15, Pg. 583, 1997.
women TDLo unreported 150mg/kg (150mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Cancer Vol. 48, Pg. 2158, 1981.

Safety

A human poison by intraspinal route. Poison experimentally by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Human teratogenic effects by ingestion: developmental abnormalities of the craniofacial area and the musculoskeletal system. Human systemic effects by multiple routes: thrombocytopenia (decrease in the number of blood platelets), bone marrow changes, other blood changes, cerebral spinal fluid effects, eye effects, blood pressure lowering, cough, dyspnea, fibrosis (pneumoconiosis), cyanosis, gastrointestinal effects, fatty liver degeneration, hepatitis, impairment of liver function tests, other liver changes, fever, effects on inflammation or mediation of inflammation, leukopenia. Human mutation data reported. Experimental reproductive effects. A human eye irritant. Questionable human carcinogen producing leukemia, Hodgkin's disease, and skin tumors. An FDA proprietary drug. A chemotherapeutic agent. When heated to decomposition it emits toxic fumes including NOx.
Hazard Codes:?T
Risk Statements: 61-25-36/38-46?
R61: May cause harm to the unborn child.?
R25: Toxic if swallowed.?
R36/38: Irritating to eyes and skin.?
R46: May cause heritable genetic damage.
Safety Statements: 53-26-36/37-45-36/37/39
S53: Avoid exposure - obtain special instructions before use.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: MA1225000
F: 3-8-10
HazardClass: 6.1(b)
PackingGroup: III

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