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Merck

PHR1396

Methotrexate

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):

Methotrexate, (+)-Amethopterin, 4-Amino-10-methylfolic acid, 4-Amino-N10-methylpteroyl-L-glutamic acid, Antifolan, MTX, Methylaminopterin

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About This Item

Empirical Formula (Hill Notation):
C20H22N8O5
CAS Number:
59-05-2
Molecular Weight:
454.44
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329823370
EC Number:
200-413-8
Beilstein/REAXYS Number:
70669
MDL number:
MFCD00064370

Product Name

Methotrexate, Pharmaceutical Secondary Standard; Certified Reference Material

InChI key

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

SMILES string

CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O

grade

certified reference material
pharmaceutical secondary standard

agency

traceable to Ph. Eur. M1000000
traceable to USP 1414003

API family

methotrexate

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Quality Level

300

Gene Information

human ... DHFR(1719)

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Analysis Note

These secondary standards offer multi-traceability to the USP and EP (PhEur) primary standards, where they are available.

Application

Methotrexate may be used as a pharmaceutical secondary reference standard for the determination of the analyte in plasma samples and pharmaceutical formulations by various techniques.
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Methotrexate is an antagonist of folic acid that inhibits dihydrofolate reductase (DHFR) enzyme, reversibly and results in impaired DNA synthesis and cellular replication. Methotrexate has been used in treatment of rheumatoid arthritis and also for maintenance therapy in childhood acute lymphocytic leukemia (ALL).

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.
To see an example of a Certificate of Analysis for this material enter LRAB9958 in the slot below. This is an example certificate only and may not be the lot that you receive.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Muta. 2 - Repr. 1B - STOT RE 1

target_organs

Liver,Bone marrow

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fetal methotrexate syndrome: A systematic review of case reports
Verberne EA, et al.
Reproductive Toxicology, 87, 125-139 (2019)
Methotrexate mechanism in treatment of rheumatoid arthritis
Friedman B and Cronstein B
Joint, Bone, Spine : Revue du Rhumatisme, 86(3), 301-307 (2018)
Determination of methotrexate in plasma by on-column concentration and ion-exchange chromatography
Lankelma J and Poppe H
Journal of Chromatography A, 149(5), 587-598 (1978)
Methotrexate bioavailability after oral and intramuscular administration in children
Teresi ME, et al.
The Journal of Pediatrics, 110(5), 788-792 (1987)
Methotrexate determination in pharmaceuticals by enantioselective HPLC
El-Hady DA, et al.
Journal of Pharmaceutical and Biomedical Analysis, 37(5), 919-925 (2005)
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