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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22N8O5
Molecular Weight 454.4393
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHOTREXATE

SMILES

CN(CC1=NC2=C(N)N=C(N)N=C2N=C1)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI

InChIKey=FBOZXECLQNJBKD-ZDUSSCGKSA-N
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

HIDE SMILES / InChI
Molecular Formula C20H22N8O5
Molecular Weight 454.4393
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:07:58 UTC 2023
Edited
by admin
on Sat Dec 16 20:07:58 UTC 2023
Record UNII
YL5FZ2Y5U1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOTREXATE
EP   HSDB   INN   MART.   MI   USAN   USP   VANDF   WHO-DD   WHO-IP  
INN   INCI   USAN  
Official Name English
METHOTREXATE [WHO-IP]
Common Name English
METHOTREXATE [USP-RS]
Common Name English
METHYLAMINOPTERIN
Common Name English
METHOTREXATE [EP MONOGRAPH]
Common Name English
Methotrexate [WHO-DD]
Common Name English
methotrexate [INN]
Common Name English
METHOTREXATUM [WHO-IP LATIN]
Common Name English
METHOTREXATE [IARC]
Common Name English
METHOTREXATE [USAN]
Common Name English
METHOTREXATE [ORANGE BOOK]
Common Name English
AMETHOPTERIN
Common Name English
XATMEP
Brand Name English
METHOTREXATE [MART.]
Common Name English
ADX-2191
Code English
METHOTREXATE [MI]
Common Name English
REDITREX
Brand Name English
R-9985
Code English
CL-14377
Code English
METHOTREXATE [USP MONOGRAPH]
Common Name English
METHOTREXATE [INCI]
Common Name English
METHOTREXATE [HSDB]
Common Name English
MTX
Common Name English
RASUVO
Brand Name English
METHOTREXATE [USP IMPURITY]
Common Name English
CL 14377
Code English
NSC-740
Code English
METHOTREXATE [JAN]
Common Name English
(2S)-2-((4-(((2,4-DIAMINOPTERIDIN-6-YL)METHYL)(METHYL)AMINO)BENZOYL)AMINO)PENTANEDIOIC ACID
Systematic Name English
METHOTREXATE [VANDF]
Common Name English
JYLAMVO
Brand Name English
Classification Tree Code System Code
IARC Methotrexate
FDA ORPHAN DRUG 469315
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
LIVERTOX NBK548219
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 440314
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 679019
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
WHO-VATC QL01BA01
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 479515
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
NCI_THESAURUS C511
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 76693
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 754320
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 829121
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
WHO-ATC L01BA01
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
NDF-RT N0000175584
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
NCI_THESAURUS C2153
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
EU-Orphan Drug EU/3/07/495
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 286409
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 479615
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
WHO-VATC QL04AX03
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
NDF-RT N0000000111
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
WHO-ATC L04AX03
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 43389
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
FDA ORPHAN DRUG 630518
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL34259
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
FDA UNII
YL5FZ2Y5U1
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
RS_ITEM_NUM
1414003
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
RXCUI
6851
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m7327
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY Merck Index
PUBCHEM
126941
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
CHEBI
50681
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
DRUG BANK
DB00563
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
DRUG CENTRAL
1751
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
SMS_ID
100000090250
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-413-8
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
HSDB
3123
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
CAS
59-05-2
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
IUPHAR
4815
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHOTREXATE
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY Description: A yellow to orange, crystalline powder. Solubility: Practically insoluble in water, ethanol (~750 g/l) TS, dichloroethane R, and ether R; very soluble in diluted solutions of alkali hydroxides and carbonates. Category: Cytotoxic drug.Storage: Methotrexate should be kept in a tightly closed container, protected from light. Additional information: Methotrexate is gradually affected by light. CAUTION: Methotrexate must be handled with care, avoiding contact with the skin and inhalation of airborne particles. Definition: Methotrexate contains not less than 96.0% and not more than 102.0% of C20H22N8O5, calculated with reference to the anhydrous substance.
EPA CompTox
DTXSID4020822
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
CHEBI
44185
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
INN
926
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
WIKIPEDIA
METHOTREXATE
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
UCSF-FDA TRANSPORTAL
Methotrexate
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
LACTMED
Methotrexate
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
DAILYMED
YL5FZ2Y5U1
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
MESH
D008727
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
NCI_THESAURUS
C642
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
EVMPD
SUB08856MIG
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
NSC
740
Created by admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
PRIMARY
Related Record Type Details
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
OATP-8
TRANSPORTER -> SUBSTRATE
Structure of METHOTREXATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
OATP1B1
TRANSPORTER -> SUBSTRATE
Structure of METHOTREXATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of METHOTREXATE MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of MX-68
DERIVATIVE -> PARENT
Structure of METHOTREXATE SODIUM
SALT/SOLVATE -> PARENT
OAT-2
TRANSPORTER -> SUBSTRATE
OAT-1
TRANSPORTER -> SUBSTRATE
DIHYDROFOLATE REDUCTASE
TARGET -> INHIBITOR
Structure of METHOTREXATE, (±)-
RACEMATE -> ENANTIOMER
MRP-1
TRANSPORTER -> SUBSTRATE
OAT-3
TRANSPORTER -> SUBSTRATE
MRP-2
TRANSPORTER -> SUBSTRATE
MRP-3
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of 7-HYDROXYMETHOTREXATE
METABOLITE -> PARENT
Structure of 10-FORMYL-7,8-DIHYDROFOLIC ACID
METABOLITE -> PARENT
Structure of 4-AMINO-4-DEOXY-N10-METHYLPTEROIC ACID
METABOLITE INACTIVE -> PARENT
URINE
Structure of 7-HYDROXYMETHOTREXATE
METABOLITE TOXIC -> PARENT
7-OH-MTX levels were correlated with nephrotoxicity in adolescents.
Related Record Type Details
Structure of 4-AMINO-4-DEOXY-N10-METHYLPTEROIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of METHOTREXATE 1-METHYL ESTER
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of AMINOPTERIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-(P-AMINOBENZOYL)GLUTAMIC ACID
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N10-METHYLPTEROIC ACID
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHOTREXATE 1-METHYL ESTER
IMPURITY -> PARENT
If present, methotrexate dimethylamide and Methotrexate related compound I may not be completely resolved by the method. These peaks are integrated together to determine conformance (NMT 0.2%)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N10-METHYLFOLIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2,4-DIAMINO-6-HYDROXYMETHYLPTERIDINE
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-AMINO-4-DEOXY-N10-METHYLPTEROIC ACID
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.8
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N10-METHYLFOLIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of AMINOPTERIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of METHOTREXATE, (R)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHOTREXATE 5-METHYL ESTER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-(P-(METHYLAMINO)BENZOYL)GLUTAMIC ACID
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DIMETHYL METHOTREXATE
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (2S)-2-((4-((4-(((2,4-DIAMINOPTERIDIN-6-YL)METHYL)METHYLAMINO)BENZOYL)METHYLAMINO)BENZOYL)AMINO)PENTANEDIOIC ACID
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHOTREXATE 5-METHYL ESTER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of METHOTREXATE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Population
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC Steady state
PHARMACOKINETIC
Initial
PHARMACOKINETIC
NIH
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