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Substance Name: Methotrexate [USAN:USP:INN:BAN:JAN]
RN: 59-05-2
UNII: YL5FZ2Y5U1
InChIKey: FBOZXECLQNJBKD-ZDUSSCGKSA-N

Note

  • 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.

Molecular Formula

  • C20-H22-N8-O5

Molecular Weight

  • 454.4448
 

Classification Codes

Classification Codes

  • Abortifacient Agents
  • Abortifacient Agents, Nonsteroidal
  • Agricultural Chemical
  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Antirheumatic Agents
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Insecticide
  • Mutation Data
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Control Agents
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Methotrexate
  • Methotrexate [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Methotrexate

Synonyms

  • 4-Amino-10-methylfolic acid
  • 4-Amino-N(sup 10)-methylpteroylglutamic acid
  • 4-Aminomethylpteroylglutamic acid
  • A-Methopterin
  • A-Methpterin
  • Abitrexate
  • AI3-25299
  • alpha-Methopterin
  • Amethopterin
  • Amethopterin L-
  • Antifolan
  • Brimexate
  • CCRIS 1109
  • CL 14377
  • CL-14377
  • EINECS 200-413-8
  • EMT 25,299
  • Emtexate
  • Emthexat
  • Emthexate
  • Farmitrexat
  • Fauldexato
  • Folex
  • Folex PFS
  • Folex-Pfs
  • Hdmtx
  • HSDB 3123
  • Kyselina 4-amino-N(sup 10)-methylpteroylglutamova
  • Kyselina 4-amino-N(sup 10)-methylpteroylglutamova [Czech]
  • Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-L-glutamova
  • Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-L-glutamova [Czech]
  • L-(+)-N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)glutamic acid
  • L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
  • Lantarel
  • Ledertrexate
  • Lumexon
  • Maxtrex
  • Medsatrexate
  • Metatrexan
  • Metex
  • Methoblastin
  • Methotrexat-Ebewe
  • Methotrexate
  • Methotrexate LPF
  • Methotrexate, L-
  • Methotrexatum
  • Methotrexatum [INN-Latin]
  • Methylaminopterin
  • Methylaminopterinum
  • Metotressato
  • Metotressato [DCIT]
  • Metotrexato
  • Metotrexato [INN-Spanish]
  • Metrotex
  • Mexate
  • Mexate-AQ
  • MPI-2505
  • MTX
  • N-(4-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamicacid
  • N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-(+)-glutamic acid
  • N-(p-(((2,4-Diamino-6-pteridyl)methyl)methylamino)benzoyl)glutamic acid
  • N-Bismethylpteroylglutamic acid
  • NCI-C04671
  • Novatrex
  • NSC 740
  • NSC-740
  • Otrexup
  • R 9985
  • Rasuvo
  • Rheumatrex
  • Texate
  • Tremetex
  • Trexeron
  • Trixilem
  • UNII-YL5FZ2Y5U1
  • WR-19039
  • X 133
  • Xatmep

Systematic Names

  • Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L-
  • L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
  • Methotrexate

Superlist Name

  • Methotrexate

Registry Numbers

CAS Registry Number

  • 59-05-2

FDA UNII

  • YL5FZ2Y5U1

Other Registry Number

  • 1082707-84-3

Related Registry Numbers

  • 15475-56-6 (hydrochloride salt)
  • 7413-34-5 (di-hydrochloride salt)

System Generated Number

  • 0000059052

Structure Descriptors

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)/t13-/m0/s1

InChIKey

FBOZXECLQNJBKD-ZDUSSCGKSA-N

Smiles

CN(Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O

Toxicity

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

BLOOD: THROMBOCYTOPENIA
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) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
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: LIVER FUNCTION TESTS IMPAIRED

LIVER: FATTY LIVER DEGERATION
Proceedings of the American Association for Cancer Research. Vol. 5, Pg. 26, 1964.
human TDLo intravenous 7143ug/kg (7.143mg/kg) BLOOD: CHANGES IN PLATELET COUNT

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT

GASTROINTESTINAL: NAUSEA OR VOMITING
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 673, 1992.
human TDLo oral 43mg/kg/5Y (43mg/kg) LIVER: OTHER CHANGES

LIVER: LIVER FUNCTION TESTS IMPAIRED
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)"

BLOOD: APLASTIC ANEMIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION
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.
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.
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)   New England Journal of Medicine. Vol. 289, Pg. 770, 1973.
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: OXIDANT RELATED (GPD DEFICIENT) ANEMIA

BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA
Medical Journal of Australia. Vol. 155, Pg. 493, 1991.
women TDLo oral 2mg/kg/17W-I (2mg/kg) BLOOD: LEUKOPENIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
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: DYSPNEA

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

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 4.7 (none)   EXP
log P (octanol-water) -1.85E+00 (none)   EXP
Water Solubility 2600 mg/L 25 EST
Vapor Pressure 2.09E-19 mm Hg 25 EST
Henry's Law Constant 1.54E-31 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.17E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.