M7824

Methotrexate

Name: Methotrexate
Brand: SIGMA

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

EC Number:

200-413-8

UNSPSC Code:

41116107

NACRES:

NA.21

Beilstein/REAXYS Number:

70669

MDL number:

MFCD00064370

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

InChI key

FBOZXECLQNJBKD-ZDUSSCGKSA-N

SMILES string

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

biological source

synthetic

form

powder

suitability

suitable for manufacturing use

storage temp.

−20°C

Quality Level

400

Gene Information

human ... DHFR(1719)

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Bioprocessing & Formulation Raw Materials

Pharma & Biopharma Manufacturing

Upstream Process Chemicals

General description

Inhibits thymidylate synthetase, is a nonselective de novo purine synthesis inhibitor and has a significant toxicity profile including hepatotoxicity, pneumonitis and bone marrow suppression. Potent folic acid antagonist. Induces apoptosis in HL-60 human leukemia cells. Also useful as an anti-tumor agent.

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Legal Information

SAFC is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H341,H360D,H372

pcodes

P202 - P260 - P264 - P280 - P301 + P310 - P405

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000507508

0000491173

0000502828

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Deep sequencing reveals different compositions of mRNA transcribed from the F8 gene in a panel of FVIII-producing CHO cell lines.

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Biotechnology journal, 10(7), 1081-1089 (2015-05-13)

Coagulation factor VIII (FVIII) is one of the most complex biopharmaceuticals due to the large size, poor protein stability and extensive post-translational modifications. As a consequence, efficient production of FVIII in mammalian cells poses a major challenge, with typical yields

Early MRI measures independently predict 1-year and 2-year radiographic progression in rheumatoid arthritis: secondary analysis from a large clinical trial.

Joshua F Baker et al.

Annals of the rheumatic diseases, 73(11), 1968-1974 (2013-08-02)

To determine if early MRI measures predict X-ray progression at 1 and 2 years in a large RA trial cohort. This study included 256 methotrexate (MTX)-naïve RA patients from a randomised placebo-controlled trial of golimumab (GO-BEFORE). MRIs of wrist and 2nd-5th

How much does Disease Activity Score in 28 joints ESR and CRP calculations underestimate disease activity compared with the Simplified Disease Activity Index?

Roy Fleischmann et al.

Annals of the rheumatic diseases, 74(6), 1132-1137 (2014-08-22)

Disease Activity Score in 28 joints calculated with C-reactive protein (DAS28-CRP) is used instead of erythrocyte sedimentation rate (DAS28-ESR) to assess rheumatoid arthritis disease activity; however, values for remission and low disease activity (LDA) for DAS28-CRP have not been validated.

Rates of serious infections and malignancies among patients with rheumatoid arthritis receiving either tumor necrosis factor inhibitor or rituximab therapy.

Kalle Jyri Aaltonen et al.

The Journal of rheumatology, 42(3), 372-378 (2015-01-17)

Because of the role of tumor necrosis factor (TNF) in host defense, it was hypothesized that its inhibition might lead to an increased risk of malignancies and infections. The objective of our study was to assess the incidence of serious

Methotrexate in chronic-recurrent calcium pyrophosphate deposition disease: no significant effect in a randomized crossover trial.

Axel Finckh et al.

Arthritis research & therapy, 16(5), 458-458 (2014-10-16)

Calcium pyrophosphate deposition (CPPD) may cause severe arthropathy, major joint destruction and treatment options are limited. The aim of this study was to test the therapeutic efficacy of methotrexate (MTX) in chronic or recurrent CPPD arthropathy. Patients with CPPD arthropathy

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