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IUPAC_Name: (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
InChI InChI=1S/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)

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

Acide N-(4-{[(2,4-diamino-6-ptéridinyl)méthyl](méthyl)amino}benzoyl)-L-glutamique

Canonical SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
Physical Description:

PHYSICAL DESCRIPTION: Odorless yellow to orange-brown crystalline powder. (NTP, 1992) It is a chemotherapy drug that interferes with DNA and RNA synthesis.

Orange-brown, crystalline powder:Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 722

Melting Point: 365 to 399° F (decomposes) (NTP, 1992)
Solubility: less than 1 mg/mL at 66° F (NTP, 1992)
Stability: Stable, but light sensitive and hygroscopic. Incompatible withstrong acids, strong oxidizing agents. Store at -15C or below.
Density: 1.5±0.1 g/cm3
Index of Refraction: 1.738
Molar Refractivity: 119.0±0.3 cm3
Experimental Solubility: 100 mM in DMSO
Appearance: yellow powder
Vapor Pressure: 2.1X10-19 mm Hg at 25 deg C /Estimated/
Storage Conditions: Methotrexate sodium tablets should be protected from light and stored in well-closed containers at 15-30 deg C. Methotrexate sodium injection and powder for injection should be protected from light and stored at 15-30 deg C. /Methotrexate sodium/
Decomposition: When heated to decomposition it emits toxic fumes including /nitrogen oxides/.
Analytic Laboratory Methods: Analyte: methotrexate; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards
Reactive Group: Acids, Carboxylic
Amides and Imides
Amines, Phosphines, and Pyridines
Drug Indication: Methotrexate is indicated in the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole. In acute lymphocytic leukemia, methotrexate is indicated in the prophylaxis of meningeal leukemia and is used in maintenance therapy in combination with other chemotherapeutic agents. Methotrexate is also indicated in the treatment of meningeal leukemia. Methotrexate is used alone or in combination with other anticancer agents in the treatment of breast cancer, epidermoid cancers of the head and neck, advanced mycosis fungoides (cutaneous T cell lymphoma), and lung cancer, particularly squamous cell and small cell types. Methotrexate is also used in combination with other chemotherapeutic agents in the treatment of advanced stage non-Hodgkin’s lymphomas. Methotrexate is indicated in the symptomatic control of severe, recalcitrant, disabling psoriasis. Methotrexate is indicated in the management of selected adults with severe, active rheumatoid arthritis (ACR criteria), or children with active polyarticular-course juvenile rheumatoid arthritis.
Safety: Danger
Health Hazard: SYMPTOMS: Symptoms of exposure to this compound include renal damage, leukopenia, headache, drowsiness, blurred vision, aphasia and hemiparesis. In addition, it causes developmental abnormalities of the craniofacial area and the musculoskeletal system, carcinogenic effects, leukemia, lymphoma effects including Hodgkin's disease, thrombocytopenia, 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 and other liver changes, hepatitis, impaired liver function tests, skin tumors, fever, effects on inflammation or mediation of inflammation. Other symptoms include hemorrhagic enteritis, dermatitis, interstitial pneumonitis, neurotoxicity, nephrotoxicity, defective oogenesis o spermatogenesis, teratogenesis, hepatic dysfunction, progressive weight loss, depression, swelling and cytoplasmic vacuolization of the mucosal cells of the intestinal epithelium, desquamation of epithelial cells, extrusion of plasma into the lumen of the bowel, leukocytic infiltration of the submucosa, disturbance in the maturation of erythrocytes, rapid pathological alteration in myelopoiesis, diminution in content of lymphoid cells in lymphatic tissue and interference with embryogenesis. Interference with cellular reproduction, embryotoxicity, abortion, fetal defects, fertility impairment, menstrual dysfunction, hematopoiesis suppression, acute and chronic hepatotoxicity, nonspecific pneumonitis, chemical arachnoiditis manifested by headache, back pain and nuchal rigidity, paresis manifested by paraplegia, leukoencephalopathy manifested by confusion, irritability, somnolence, ataxia, dementia and convulsions, ulcerative stomatitis, nausea, alopecia, ecchymosis, telangiectasia, acne, furunculosis, vomiting, diarrhea, gastrointestinal ulceration and bleeding, azotemia, cystitis, hematuria, vaginal discharge, arthralgia, myalgia, metabolic changes, precipitating diabetes, osteoporotic effects, abdominal distress, malaise, undue fatigue, chills, dizziness, reduce resistance to infection, erythematous rash, pruritus, urticaria, gingivitis, photosensitivity, pigmentary changes, pharyngitis, anorexia, hematemesis, melena, transient oligospermia and sudden death may also result. In children it can cause pulmonary tract damage by ingestion, and blood dyscrasia intravenously. It may also cause lung changes, uro-genital toxicity and conjunctivitis. It may also cause septicemia and bleeding from various sites, mucositis, cerebral and cerebellar calcification, bone pain, fractures, aseptic necrosis of the head of the femur and shortness of breath. Granulocytopenia, hypoplasia of all elements of bone marrow and anemia may also occur. It may cause congenital malformation in the fetus and alter genetic material. Ulceration of the mouth, megaloblastic anemia, hypogammaglobulinemia, kidney damage, pulmonary reactions, progressive intellectual impairment, coma and pyrexia may also occur. ACUTE/CHRONIC HAZARDS: This compound can cause eye irritation. It may be absorbed through the skin and may be fatal if inhaled, swallowed or absorbed through the skin. It is readily absorbed through the gastrointestinal tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)
Fire Hazard: Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
GHS Classification:
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 77 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
H315 (94.81%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (96.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H340 (33.77%): May cause genetic defects [Danger Germ cell mutagenicity]
H360 (94.81%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P264, P270, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P405, and P501
Air and Water Reactions: This chemical is sensitive to hydrolysis, oxidation and light. Insoluble in water.
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