(Q422232)

cellular response to methotrexate

part of

subject has role

reactant

1 reference

Gene Ontology release 2019-11-16

methotrexate transmembrane transporter activity

subject has role

cargo

1 reference

Gene Ontology release 2019-11-16

response to methotrexate

subject has role

reactant

1 reference

Gene Ontology release 2020-05-02

has use

medication

0 references

chemical structure

Methotrexate2DACS2.svg
708 × 337; 20 KB

1 reference

imported from Wikimedia project

English Wikipedia

mass

454.171 dalton

1 reference

methotrexate (English)

19 October 2016

2 references

inferred from InChI

chemical formula

C₂₀H₂₂N₈O₅

1 reference

methotrexate (English)

19 November 2016

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

1 reference

methotrexate (English)

19 November 2016

isomeric SMILES

CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O

1 reference

methotrexate (English)

19 November 2016

defined daily dose

2.5 milligram

oral administration

1 reference

https://www.whocc.no/atc_ddd_index/?code=L04AX03

active ingredient in

Nordimet

1 reference

European Medicines Agency product number

EMEA/H/C/003983

http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/003983/human_med_002015.jsp

22 March 2017

1 reference

14 February 2018

1 reference

14 February 2018

1 reference

14 February 2018

1 reference

14 February 2018

1 reference

14 February 2018

World Health Organisation international non-proprietary name

methotrexate (English)

1 reference

Detection and quantification of maitotoxin-like compounds using a neuroblastoma (Neuro-2a) cell based assay. Application to the screening of maitotoxin-like compounds in Gambierdiscus spp.

methotrexate (English)

19 October 2016

1 reference

Asimina triloba

1 reference

Antiangiogenic Activity and Chemical Derivatization of the Neurotoxic Acetogenin Annonacin Isolated from Asimina triloba

Quambalaria cyanescens

1 reference

Quambalarine B, a Secondary Metabolite from Quambalaria cyanescens with Potential Anticancer Properties.

Dolichousnea longissima

1 reference

Usnic Acid Derivatives with Cytotoxic and Antifungal Activities from the Lichen Usnea longissima.

medical condition treated

1 reference

13 December 2016

1 reference

13 December 2016

1 reference

13 December 2016

trophoblastic neoplasm

1 reference

13 December 2016

1 reference

13 December 2016

1 reference

juvenile rheumatoid arthritis

13 December 2016

1 reference

13 December 2016

1 reference

13 December 2016

2 references

13 December 2016

2 October 2018

1 reference

13 December 2016

1 reference

13 December 2016

2 references

13 December 2016

2 October 2018

1 reference

13 December 2016

2 references

13 December 2016

2 October 2018

1 reference

13 December 2016

1 reference

2 October 2018

ankylosing spondylitis

1 reference

precursor T-cell lymphoblastic leukemia

2 October 2018

1 reference

granulomatosis with polyangiitis

2 October 2018

1 reference

2 October 2018

acute myeloid leukemia

1 reference

precursor T-cell acute lymphoblastic leukemia

2 October 2018

1 reference

2 October 2018

ectopic pregnancy

1 reference

2 October 2018

polymyositis

1 reference

diffuse large B-cell lymphoma

2 October 2018

1 reference

2 October 2018

T-cell lymphoma

1 reference

2 October 2018

polymyalgia rheumatica

1 reference

2 October 2018

ulcerative colitis

1 reference

2 October 2018

non-Hodgkin lymphoma

1 reference

2 October 2018

uveitis

1 reference

2 October 2018

bone sarcoma

1 reference

acute promyelocytic leukemia

2 October 2018

1 reference

2 October 2018

B-cell lymphoma

1 reference

osteoarthritis susceptibility 1

2 October 2018

1 reference

2 October 2018

arthritis

1 reference

2 October 2018

giant cell arteritis

1 reference

systemic-onset juvenile idiopathic arthritis

2 October 2018

1 reference

central nervous system lymphoma

2 October 2018

1 reference

precursor B-cell acute lymphoblastic leukemia

2 October 2018

1 reference

2 October 2018

bullous pemphigoid

1 reference

significant drug interaction

2 October 2018

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

foscarnet

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

celecoxib

1 reference

A reference set of clinically relevant adverse drug-drug interactions

meloxicam

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

parecoxib

1 reference

A reference set of clinically relevant adverse drug-drug interactions

aceclofenac

1 reference

A reference set of clinically relevant adverse drug-drug interactions

bone marrow failure

1 reference

A reference set of clinically relevant adverse drug-drug interactions

bone marrow failure

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

megaloblastic anemia

1 reference

A reference set of clinically relevant adverse drug-drug interactions

pancytopenia

1 reference

A reference set of clinically relevant adverse drug-drug interactions

bone marrow toxicity

1 reference

A reference set of clinically relevant adverse drug-drug interactions

megaloblastic anemia

1 reference

A reference set of clinically relevant adverse drug-drug interactions

pancytopenia

1 reference

A reference set of clinically relevant adverse drug-drug interactions

bone marrow toxicity

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

1 reference

A reference set of clinically relevant adverse drug-drug interactions

acitretin

hepatotoxicity

1 reference

A reference set of clinically relevant adverse drug-drug interactions

physically interacts with

solute carrier family 46 member 1

1 reference

4674

solute carrier family 19 member 1

17 August 2016

1 reference

4674

17 August 2016

intravenous infusion and defusion

oral administration

0 references

0 references

intramuscular injection

0 references

intrathecal administration

0 references

legal status (medicine)

boxed warning

1 reference

https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802

Australian pregnancy category D

FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links. (English)

pregnancy category

1 reference

imported from Wikimedia project

English Wikipedia

US pregnancy category X

1 reference

imported from Wikimedia project

1 reference

https://www.pfizer.com/products/product-list

1 reference

5 March 2018

disease-modifying antirheumatic drug

1 reference

15 March 2018

1 reference

Abortifacient Agents, Nonsteroidal

15 March 2018

1 reference

antineoplastic antimetabolite

15 March 2018

1 reference

15 March 2018

1 reference

15 March 2018

folic acid antagonists

1 reference

15 March 2018

immunosuppressive drug

1 reference

DNA polymerase inhibitors

15 March 2018

1 reference

15 March 2018

0 references

developmental toxicant

start time

1 January 1989

1 reference

California Proposition 65 list of chemicals

18 March 2020

https://oehha.ca.gov/chemicals/methotrexate

Commons category

Methotrexate

0 references

Identifiers

GND ID

4038985-6

0 references

National Library of Israel J9U ID

987007529313305171

1 reference

National Library of Israel

Library of Congress authority ID

sh85084418

subject named as

Methotrexate

1 reference

Integrated Authority File

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/s1

1 reference

methotrexate (English)

19 November 2016

2 references

methotrexate (English)

19 November 2016

ChEBI release 2020-09-01

CAS Registry Number

59-05-2

2 references

methotrexate (English)

19 November 2016

https://commonchemistry.cas.org/detail?cas_rn=59-05-2

10 April 2021

1 reference

Methotrexate (English)

19 November 2016

2 references

methotrexate (English)

19 November 2016

Reaxys registry number

70669

0 references

ChEBI ID

44185

mapping relation type

3 references

METHOTREXATE (English)

19 November 2016

ChEBI release 2019-10-02

International Chemical Identifier

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/s1

1 reference

METHOTREXATE (English)

19 November 2016

2 references

MSBNK-Athens_Univ-AU273001

1 reference

MassBank accession ID

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-Athens_Univ-AU273002

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-Athens_Univ-AU273004

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-Athens_Univ-AU273006

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-Athens_Univ-AU273005

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-Athens_Univ-AU273003

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

splash10-0fai-6900000000-25b0e287457fb3845ef4

0 references

0 references

0 references

1 reference

Hazardous Substances Data Bank

28 October 2019

METHOTREXATE (English)

10 May 2021

2 references

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

0 references

0 references

200-413-8

1 reference

methotrexate (English)

ECHA Substance Infocard ID

19 November 2016

100.000.376

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.000.376

27 December 2018

OSHA Occupational Chemical Database ID

Methotrexate (English)

quotation

CAS no.: 59-05-2 (English)

0 references

1 reference

28 December 2019

METHOTREXATE (English)

quotation

CAS no.: 59-05-2 (English)

1 reference

Methotrexate (English)

17 November 2015

1 reference

Methotrexate (English)

17 November 2015

0 references

0 references

4815

1 reference

4815

methotrexate (English)

19 November 2016

4674

1 reference

D03.633.100.733.631.192.500

5 February 2021

Methotrexate

0 references

MeSH concept ID

M0013595

0 references

MeSH tree code

0 references

RxNorm ID

6851

1 reference

methotrexate (English)

19 November 2016

DrugBank ID

DB00563

1 reference

Human Metabolome Database ID

HMDB0014703

2 references

2 references

methotrexate (English)

19 November 2016

MedlinePlus drug identifier

a682019

oral administration

0 references

a682018

PatientsLikeMe treatment ID

injection

0 references

0 references

1 reference

methotrexate (English)

19 November 2016

0 references

1 reference

1 reference

Immune Epitope Database and Analysis Resource

methotrexate (English)

19 October 2016

1 reference

1 March 2022

0 references

1 reference

California Proposition 65 list of chemicals

6 January 2020

https://oehha.ca.gov/chemicals/methotrexate

DeCS ID

28169

0 references

electronic Essential Medicines List medicine ID

99

1 reference

https://list.essentialmeds.org/medicines/99

eEML - Electronic Essential Medicines List (English)

Encyclopædia Britannica Online ID

23 October 2021

science/methotrexate

subject named as

methotrexate

0 references

1 reference

28 October 2013

Gran Enciclopèdia Catalana ID

metotrexat

0 references

Gran Enciclopèdia Catalana ID (former scheme)

0123343

0 references

Microsoft Academic ID

0 references

0 references

0 references

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

1 reference

1DLS (English)

19 October 2016

1 reference

1RB3 (English)

19 October 2016

1 reference

2OIP (English)

19 October 2016

1 reference

4L8F (English)

19 October 2016

1 reference

4L8W (English)

19 October 2016

1 reference

1D1G (English)

19 October 2016

1 reference

1DF7 (English)

19 October 2016

1 reference

1RH3 (English)

19 October 2016

1 reference

1RX3 (English)

19 October 2016

1 reference

1E7W (English)

19 October 2016

1 reference

4Q0D (English)

19 October 2016

1 reference

3TQ9 (English)

19 October 2016

1 reference

3IX9 (English)

19 October 2016

1 reference

1DHJ (English)

19 October 2016

1 reference

1DHI (English)

19 October 2016

1 reference

2C7V (English)

19 October 2016

1 reference

4DFR (English)

19 October 2016

1 reference

4GH8 (English)

19 October 2016

1 reference

1TDR (English)

19 October 2016

1 reference

3CL9 (English)

19 October 2016

1 reference

4P66 (English)

19 October 2016

1 reference

4P68 (English)

19 October 2016

1 reference