e-Drug3D

103

METHOTREXATE


INN
METHOTREXATE

cas 59-05-2
CLASS

ANTINEOPLASTIC
FOLIC ACID ANTAGONISTS
IMMUNOSUPPRESSIVE AGENTS
NUCLEIC ACID SYNTHESIS INHIBITORS
ANTIMETABOLITES
TREATMENT OF SEVERE PSORIASIS AND ADULT RHEUMATOID ARTHRITIS
ANTIMALARIALS

ROUTE (list)

ORAL INJECTION SUBCUTANEOUS INTRAVENOUS

ATC code

L01BA01
L04AX03

PK parameters

F 60 PERCENT
Tmax 1.5 HOUR
VD 39 LITER (65 KILOGRAM)
Cl 8.2 LITER / HOUR (65 KILOGRAM)
PPB 50 PERCENT
t1/2 7.5 HOUR

Target

TARGET DIHYDROFOLATE REDUCTASE

PDB
5X66 (HUMAN THYMIDYLATE SYNTHASE IN COMPLEX WITH DUMP AND METHOTREXATE)

Ligand code = MTX (link to the list of PDB complexes)

Download experimental 3D coordinates of MTX with added hydrogens

DrugCentral

Dihydrofolate reductase UNIPROT P00374 DHFR

Download SDF file (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid

Formula:
C20H22N8O5

Calculated chemical properties:

MW 452.44
NB_atoms 33
XLogP -2.40
PSA 189.852
NB_HD 5
NB_HA 13
fsp3 0.25
Lipinski(0=no;1=yes) 0

FDA
NDA 087695 (pdf not found) INN (METHOTREXATE SODIUM) FOLEX (PHARMACIA AND UPJOHN) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 088954 (pdf not found) INN (METHOTREXATE SODIUM) FOLEX (PHARMACIA AND UPJOHN) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089161 (pdf not found) INN (METHOTREXATE SODIUM) ABITREXATE (ABIC) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089180 (pdf not found) INN (METHOTREXATE SODIUM) FOLEX PFS (PHARMACIA AND UPJOHN) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089293 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (QUAD PHARMS) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089294 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (QUAD PHARMS) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089295 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (QUAD PHARMS) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089296 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (QUAD PHARMS) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089308 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (QUAD PHARMS) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089309 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (QUAD PHARMS) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089354 (pdf not found) INN (METHOTREXATE SODIUM) ABITREXATE (ABIC) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089355 (pdf not found) INN (METHOTREXATE SODIUM) ABITREXATE (ABIC) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 089356 (pdf not found) INN (METHOTREXATE SODIUM) ABITREXATE (ABIC) APPROVAL= - YEAR= 0 DISCONTINUED
NDA 008085 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (STRIDES PHARMA) APPROVAL= AP YEAR= 1953 DISCONTINUED
NDA 011719 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (HOSPIRA) APPROVAL= AP YEAR= 1959
NDA 086358 (pdf not found) INN (METHOTREXATE SODIUM) MEXATE (BRISTOL) APPROVAL= AP YEAR= 1979 DISCONTINUED
NDA 088760 (pdf not found) INN (METHOTREXATE SODIUM) MEXATE-AQ (BRISTOL MYERS) APPROVAL= AP YEAR= 1985 DISCONTINUED
NDA 088648 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (NORBROOK) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 089263 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ABRAXIS PHARM) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 089322 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ABRAXIS PHARM) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 089323 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ABRAXIS PHARM) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 089340 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (HIKMA) APPROVAL= AP YEAR= 1986
NDA 089341 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (HIKMA) APPROVAL= AP YEAR= 1986
NDA 089342 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (HIKMA) APPROVAL= AP YEAR= 1986
NDA 089343 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (HIKMA) APPROVAL= AP YEAR= 1986
NDA 088935 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ABRAXIS PHARM) APPROVAL= AP YEAR= 1987 DISCONTINUED
NDA 088936 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ABRAXIS PHARM) APPROVAL= AP YEAR= 1987 DISCONTINUED
NDA 088937 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ABRAXIS PHARM) APPROVAL= AP YEAR= 1987 DISCONTINUED
NDA 089158 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (PHARMACHEMIE USA) APPROVAL= AP YEAR= 1988 DISCONTINUED
NDA 089887 (pdf not found) INN (METHOTREXATE SODIUM) MEXATE-AQ PRESERVED (BRISTOL MYERS SQUIBB) APPROVAL= AP YEAR= 1989 DISCONTINUED
NDA 081099 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (BARR) APPROVAL= AP YEAR= 1990
NDA 081242 (pdf not found) INN (METHOTREXATE SODIUM) FOLEX PFS (PHARMACIA AND UPJOHN) APPROVAL= AP YEAR= 1991 DISCONTINUED
NDA 081235 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (MYLAN) APPROVAL= AP YEAR= 1992
NDA 040054 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (HIKMA) APPROVAL= AP YEAR= 1994
NDA 040233 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (DURAMED PHARMS BARR) APPROVAL= AP YEAR= 1999 DISCONTINUED
NDA 040263 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (FRESENIUS KABI USA) APPROVAL= AP YEAR= 1999
NDA 040265 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE PRESERVATIVE FREE (FRESENIUS KABI USA) APPROVAL= AP YEAR= 1999 DISCONTINUED
NDA 040266 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE PRESERVATIVE FREE (FRESENIUS KABI USA) APPROVAL= AP YEAR= 1999
NDA 040385 (pdf not found) INN (METHOTREXATE SODIUM) TREXALL (BARR) APPROVAL= AP YEAR= 2001
NDA 040632 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (HIKMA) APPROVAL= AP YEAR= 2005
NDA 040716 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (ACCORD HLTHCARE) APPROVAL= AP YEAR= 2007
NDA 040767 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (ACCORD HLTHCARE) APPROVAL= AP YEAR= 2007
NDA 040768 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (ACCORD HLTHCARE) APPROVAL= AP YEAR= 2007
NDA 090029 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (SANDOZ) APPROVAL= AP YEAR= 2009
NDA 090039 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (SANDOZ) APPROVAL= AP YEAR= 2009
NDA 040843 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (PHARMACHEMIE BV) APPROVAL= AP YEAR= 2010
NDA 040850 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE () APPROVAL= AP YEAR= 2010
NDA 040853 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE () APPROVAL= AP YEAR= 2010
NDA 200171 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE PRESERVATIVE FREE () APPROVAL= AP YEAR= 2012
NDA 201529 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (EUGIA PHARMA SPECLTS) APPROVAL= AP YEAR= 2012 DISCONTINUED
NDA 201530 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (EXTROVIS) APPROVAL= AP YEAR= 2012 DISCONTINUED
NDA 204824 (pdf not found) INN (METHOTREXATE) OTREXUP (ASSERTIO SPECLTY) APPROVAL= AP YEAR= 2013 DISCONTINUED
NDA 205776 (pdf not found) INN (METHOTREXATE) RASUVO (MEDEXUS) APPROVAL= AP YEAR= 2014
NDA 201749 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (SUN PHARM) APPROVAL= AP YEAR= 2015
NDA 207812 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ZYDUS PHARMS) APPROVAL= AP YEAR= 2017
NDA 208400 (pdf not found) INN (METHOTREXATE SODIUM) XATMEP (AZURITY) APPROVAL= AP YEAR= 2017
NDA 210040 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (AMNEAL PHARMS) APPROVAL= AP YEAR= 2017 DISCONTINUED
NDA 203407 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM PRESERVATIVE FREE (SAGENT PHARMS INC) APPROVAL= AP YEAR= 2018
NDA 210737 (pdf not found) INN (METHOTREXATE) REDITREX (NORDIC GRP) APPROVAL= AP YEAR= 2019 DISCONTINUED
NDA 210454 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (EUGIA PHARMA) APPROVAL= AP YEAR= 2020
NDA 213343 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ACCORD HLTHCARE) APPROVAL= AP YEAR= 2020
NDA 214121 (pdf not found) INN (METHOTREXATE) METHOTREXATE (ACCORD HLTHCARE) APPROVAL= AP YEAR= 2020 DISCONTINUED
NDA 209787 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (LOTUS PHARM CO LTD) APPROVAL= AP YEAR= 2021 DISCONTINUED
NDA 212479 (pdf not found) INN (METHOTREXATE) JYLAMVO (SHORLA) APPROVAL= AP YEAR= 2022
NDA 213362 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (DAITO) APPROVAL= AP YEAR= 2023
NDA 216453 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ELITE LABS INC) APPROVAL= AP YEAR= 2024
NDA 217552 (pdf not found) INN (METHOTREXATE SODIUM) METHOTREXATE SODIUM (ALEMBIC) APPROVAL= AP YEAR= 2024

Other links:

PubChem
ChemicalProbes

U.S. repository of Clinical Trials

VigiAccess
SIDER side effects

ChemSynthesis
Patent@SureChEMBL