Methotrexate hydrate - PharmPure™, USP , CAS No.133073-73-1

CAS: 133073-73-1 Cat. No.: M476589 Formula: C₂₀H₂₂N₈O₅·xH₂O Molecular Weight: 454.44 (anhydrous basis) Beilstein Registry Number: 70669 EC Number: 625-397-3

GRADE & PURITY PharmPure™, USP

Synonyms

Methylaminopterin hydrate | Antifolan hydrate | L-Amethopterin hydrate | L-4-Amino-N10-methylpteroylglutamic acid hydrate | 4-Amino-10-methylfolic acid hydrate | (+)-Amethopterin Hydrate | L(+)-Amethopterin hydrate | Methotrexate | MTX hydrate

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Description

Methotrexate hydrate has been used:as a dihydrofolate (DHFR) inhibitor in sphere forming assay cultureas a component of dulbecco′ modified Eagle′s medium (DMEM) for selection of transfected cellsin viability and co-culture assaysPotent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.Potent inhibitor of dihydrofolate reductase and agent for antitumor studies. Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistantPlasmodium vivaxmalaria parasites.

Specifications

Synonyms

Methylaminopterin hydrate | Antifolan hydrate | L-Amethopterin hydrate | L-4-Amino-N10-methylpteroylglutamic acid hydrate | 4-Amino-10-methylfolic acid hydrate | (+)-Amethopterin Hydrate | L(+)-Amethopterin hydrate | Methotrexate | MTX hydrate

Specifications & Purity

PharmPure™, USP

Biochemical and Physiological Mechanisms

Methotrexate used to inhibit dihyrofolate reductase and select for DHFR overexpresssion.Methotrexate is a folic acid antagonist.

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

PharmPure™, USP

Product Properties

ALogP

-1.8

Names and Identifiers

Pubchem Sid

508814933

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.O

IUPAC Name

(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid;hydrate

InChIKey

FPJYMUQSRFJSEW-ZOWNYOTGSA-N

INCHI

1S/C20H22N8O5.H2O/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);1H2/t13-;/m0./s1

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.O

Alternate CAS

59-05-2；6745-93-3

UN Number

1544

Molecular Weight

454.44 (anhydrous basis)

Beilstein

70669

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pteridines and derivatives
      • Subclass Pterins and derivatives
        • Level5 Pteroic acids and derivatives
          • Level6 Folic acids and derivatives
            • Level7 Folic acids

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pteridines and derivatives
• Subclass: Pterins and derivatives
• Intermediate Tree Nodes: Pteroic acids and derivatives - Folic acids and derivatives
• Direct Parent: Folic acids
• Alternative Parents: Glutamic acid and derivatives Hippuric acids N-acyl-alpha amino acids Aminobenzamides Aniline and substituted anilines Benzoyl derivatives Dialkylarylamines Aminopyrimidines and derivatives Aralkylamines Dicarboxylic acids and derivatives Imidolactams Pyrazines Heteroaromatic compounds Secondary carboxylic acid amides Amino acids Carboxylic acids Azacyclic compounds Carbonyl compounds Organic oxides Primary amines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Folic acid - Glutamic acid or derivatives - Hippuric acid or derivatives - Hippuric acid - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Aminobenzamide - Aminobenzoic acid or derivatives - Benzamide - Benzoic acid or derivatives - Benzoyl - Aniline or substituted anilines - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Aminopyrimidine - Aralkylamine - Pyrimidine - Pyrazine - Benzenoid - Imidolactam - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Heteroaromatic compound - Tertiary amine - Secondary carboxylic acid amide - Amino acid or derivatives - Amino acid - Carboxamide group - Azacycle - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Primary amine - Amine - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

DHFR Tclin Dihydrofolate reductase (0 Activities)

Discover Target: DHFR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TYMS Tclin Thymidylate synthase (0 Activities)

Discover Target: TYMS

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FOLR2 Tchem Folate receptor beta (0 Activities)

Discover Target: FOLR2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FOLR1 Tclin Folate receptor alpha (0 Activities)

Discover Target: FOLR1

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HMGB1 Tchem High mobility group protein B1 (0 Activities)

Discover Target: HMGB1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC19A1 Tchem Folate transporter 1 (0 Activities)

Discover Target: SLC19A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC46A1 Tchem Proton-coupled folate transporter (0 Activities)

Discover Target: SLC46A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ATIC Tchem Bifunctional purine biosynthesis protein PURH (0 Activities)

Discover Target: ATIC

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NCOA3 Tchem Nuclear receptor coactivator 3 (0 Activities)

Discover Target: NCOA3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)

Discover Target: SMPD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BJ (6930 Activities)

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HEK293 (82097 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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Associated Targets(non-human)

Streptococcus (3973 Activities)

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Streptococcus sp. 'group A' (3417 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ska Streptokinase A (5805 Activities)

Discover Target: ska

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LMP1 Latent membrane protein 1 (726 Activities)

Discover Target: LMP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: H2O: insoluble
• Sensitivity: Moisture sensitive；Light sensitive
• Specific Rotation[α]: 21 ° (C=0.1, 1N NaOH)
• Melt Point(°C): 205℃
• Molecular Weight: 472.500 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 472.182 Da
• Monoisotopic Mass: 472.182 Da
• Topological Polar Surface Area: 212.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 704.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3