|
|
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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Abortifacient Agents
- Abortifacient Agents, Nonsteroidal
- Agricultural Chemical
- Antimetabolites
- Antimetabolites, Antineoplastic
- Antineoplastic
- Antineoplastic Agents
- Antirheumatic Agents
- Antiviral (COVID-19)
- 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
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
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/s1InChIKey
FBOZXECLQNJBKD-ZDUSSCGKSA-NSmiles
CN(Cc1cnc2nc(N)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.