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methotrexate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
folic acid analogues	1751	59-05-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: methotrexate methotrexate sodium amethopterin amethopterine L-Amethopterin ledertrexate metatrexan methoxtrexate methylaminopterin	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 weight: 454.45 Formula: C20H22N8O5 CLOGP: -0.03 LIPINSKI: 1 HAC: 13 HDO: 5 TPSA: 210.54 ALOGS: -3.42 ROTB: 9 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

methotrexate
methotrexate sodium
amethopterin
amethopterine
L-Amethopterin
ledertrexate
metatrexan
methoxtrexate
methylaminopterin

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 weight: 454.45
Formula: C20H22N8O5
CLOGP: -0.03
LIPINSKI: 1
HAC: 13
HDO: 5
TPSA: 210.54
ALOGS: -3.42
ROTB: 9

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
2.50	mg	O
2.50	mg	P

ADMET properties:

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	81 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	33 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	3.90 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	2.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.10 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.43 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.37 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.17 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

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Date	Agency	Company
Aug. 18, 2016	EMA	Nordic Group B.V.
Dec. 7, 1953	FDA	DAVA PHARMS INC
March 26, 2019	PMDA	PFIZER JAPAN INC.

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FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug ineffective	13551.10	11.95	41090	948231	1003675	61496026
Drug intolerance	4557.13	11.95	12786	976535	295875	62203826
Treatment failure	3451.09	11.95	8758	980563	190285	62309416
Joint swelling	2839.18	11.95	11346	977975	316320	62183381
Arthralgia	2410.20	11.95	16136	973185	553574	61946127
Death	2184.75	11.95	1591	987730	372790	62126911
Therapeutic product effect incomplete	2159.75	11.95	5498	983823	119558	62380143
Drug hypersensitivity	2133.03	11.95	10033	979288	300654	62199047
Completed suicide	2087.30	11.95	36	989285	145637	62354064
Contraindicated product administered	1924.63	11.95	7590	981731	210058	62289643

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug ineffective	4818.51	11.21	12104	316938	444647	34183242
Drug intolerance	1514.49	11.21	2302	326740	57268	34570621
Joint swelling	1485.42	11.21	2288	326754	57602	34570287
Death	1397.99	11.21	1030	328012	397019	34230870
Rheumatoid arthritis	1328.43	11.21	1717	327325	36521	34591368
Treatment failure	1239.87	11.21	1842	327200	44855	34583034
Arthralgia	1157.94	11.21	3873	325169	166168	34461721
Synovitis	1113.18	11.21	979	328063	13087	34614802
Psoriasis	973.21	11.21	1491	327551	37321	34590568
Psoriatic arthropathy	911.55	11.21	1026	328016	18772	34609117

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug ineffective	12867.34	11.34	36579	993458	1044334	77670017
Drug intolerance	5075.77	11.34	10793	1019244	253326	78461025
Joint swelling	3520.85	11.34	9906	1020131	278740	78435611
Treatment failure	3327.36	11.34	7016	1023021	163470	78550881
Arthralgia	3164.24	11.34	15170	1014867	556633	78157718
Completed suicide	2857.57	11.34	66	1029971	245701	78468650
Death	2820.12	11.34	1937	1028100	564577	78149774
Drug hypersensitivity	2722.69	11.34	9268	1020769	289648	78424703
Synovitis	2266.61	11.34	5597	1024440	145137	78569214
Rheumatoid arthritis	2249.73	11.34	6853	1023184	201617	78512734

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01BA01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Folic acid analogues
ATC	L04AX03	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS IMMUNOSUPPRESSANTS IMMUNOSUPPRESSANTS Other immunosuppressants
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35705	immunosuppressive agents
CHEBI has role	CHEBI:35842	anti-rheumatic drugs
CHEBI has role	CHEBI:50177	dermatologic agent
CHEBI has role	CHEBI:50683	dihydrofolic acid reductase inhibitors
CHEBI has role	CHEBI:50691	abortifacient drug
CHEBI has role	CHEBI:59517	DNA synthesis inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Psoriasis	indication	9014002	DOID:8893
Crohn's disease	indication	34000006
Rheumatoid arthritis	indication	69896004	DOID:7148
Acute lymphoid leukemia	indication	91857003	DOID:9952
Non-Hodgkin's lymphoma	indication	118601006
Burkitt's lymphoma	indication	118617000
Mycosis fungoides	indication	118618005
Psoriatic arthritis	indication	156370009	DOID:9008
Plaque psoriasis	indication	200965009
Pustular psoriasis	indication	200973000

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.61	acidic
pKa2	5.15	acidic
pKa3	12.92	acidic
pKa4	5.73	Basic
pKa5	4.51	Basic
pKa6	1.39	Basic
pKa7	0.75	Basic
pKa8	0.08	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
10MG/0.20ML (10MG/0.20ML)	RASUVO	MEDEXUS	N205776	July 10, 2014	RX	SOLUTION	SUBCUTANEOUS	8664231	June 1, 2029	SUBCUTANEOUS INJECTION OF METHOTREXATE
10MG/0.4ML (10MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	Oct. 11, 2013	RX	SOLUTION	SUBCUTANEOUS	8480631	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
10MG/0.4ML (10MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	Oct. 11, 2013	RX	SOLUTION	SUBCUTANEOUS	8579865	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
10MG/0.4ML (10MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	Oct. 11, 2013	RX	SOLUTION	SUBCUTANEOUS	8945063	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
10MG/0.4ML (10MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	Oct. 11, 2013	RX	SOLUTION	SUBCUTANEOUS	9421333	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
12.5MG/0.25ML (12.5MG/0.25ML)	RASUVO	MEDEXUS	N205776	July 10, 2014	RX	SOLUTION	SUBCUTANEOUS	8664231	June 1, 2029	SUBCUTANEOUS INJECTION OF METHOTREXATE
12.5MG/0.4ML (12.5MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	March 24, 2016	RX	SOLUTION	SUBCUTANEOUS	8480631	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
12.5MG/0.4ML (12.5MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	March 24, 2016	RX	SOLUTION	SUBCUTANEOUS	8579865	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
12.5MG/0.4ML (12.5MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	March 24, 2016	RX	SOLUTION	SUBCUTANEOUS	8945063	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE
12.5MG/0.4ML (12.5MG/0.4ML)	OTREXUP	OTTER PHARMS	N204824	March 24, 2016	RX	SOLUTION	SUBCUTANEOUS	9421333	March 19, 2030	SUBCUTANEOUS INJECTION OF METHOTREXATE

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 2.5MG BASE/ML	XATMEP	AZURITY	N208400	April 25, 2017	RX	SOLUTION	ORAL	April 25, 2024	TREATMENT OF OLIGOARTICULAR JUVENILE IDIOPATHIC ARTHRITIS (PERSISTENT OLIGOARTHRITIS, PSORIATIC JUVENILE IDIOPATHIC ARTHRITIS, ENTHESITIS-RELATED ARTHRITIS, OR UNDIFFERENTIATED ARTHRITIS) & POLYARTICULAR JUVENILE IDIOPATHIC ARTHRITIS IN CHILDREN 0-16 YRS
EQ 2.5MG BASE/ML	XATMEP	AZURITY	N208400	April 25, 2017	RX	SOLUTION	ORAL	April 25, 2024	TREATMENT OF PEDIATRIC PATIENTS WITH ACUTE LYMPHOBLASTIC LEUKEMIA AS A COMPONENT OF A COMBINATION CHEOMOTHERAPY MAINTENANCE REGIMEN

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Dihydrofolate reductase	Enzyme	P00374	DYR_HUMAN	INHIBITOR	Ki	8.92	IUPHAR	DRUG LABEL
Canalicular multispecific organic anion transporter 1	Transporter	Q92887	MRP2_HUMAN				WOMBAT-PK
Multidrug resistance-associated protein 1	Transporter	P33527	MRP1_HUMAN				WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN				WOMBAT-PK
Thymidylate synthase	Enzyme	P04818	TYSY_HUMAN		Ki	6.22	CHEMBL
Multidrug resistance-associated protein 5	Transporter	O15440	MRP5_HUMAN				WOMBAT-PK
Folylpolyglutamate synthase, mitochondrial	Enzyme	Q05932	FOLC_HUMAN		IC50	5.49	CHEMBL
Multidrug resistance-associated protein 4	Transporter	O15439	MRP4_HUMAN				WOMBAT-PK
Folate receptor beta	Membrane receptor	P14207	FOLR2_HUMAN		IC50	6.97	CHEMBL
Proton-coupled folate transporter	Transporter	Q96NT5	PCFT_HUMAN		IC50	6.92	CHEMBL

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External reference:

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ID	Source
MTX	PDB_CHEM_ID
002644	NDDF
002645	NDDF
12261	MMSL
126941	PUBCHEM_CID
287734	RXNORM
30391	MMSL
387381009	SNOMEDCT_US
4017903	VANDF
4019828	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9367	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRA-ARTERIAL	ANDA	23 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9516	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9516	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9517	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9517	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9518	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9518	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9519	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9519	SOLUTION	25 mg	INTRA-ARTERIAL	ANDA	33 sections
Methotrexate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9830	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRA-ARTERIAL	ANDA	23 sections

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