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59-05-2 (Methotrexate)

1

Identification

Methotrexate Methotrexate
Name Methotrexate
Formula C20H22N8O5
MW 454.44
CAS No. 59-05-2
EINECS 200-413-8
Smiles NC1=C(N=C2CN(C)C3=CC=C(C(N[[email protected]](C(O)=O)CCC(O)=O)=O)C=C3)C(N=C2)=NC(N)=N1
Synonyms (+)-Amethopterin; (+)-4-Amino-10-methylfolic acid; N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamic acid; (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic acid
InChI 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
2

Introduction

Methotrexate(WR19039; CL14377) can interfere with the growth of certain cells of the body, especially cells that reproduce quickly, such as cancer cells, bone marrow cells, and skin cells. IC50 Value: Target: antifolate in vitro: In normal T cells, Methotrexate (MTX) produced a dose-dependent reduction in de novo adenosine and guanosine pools with maximal effects (>50%) at 1 microM MTX.

Background Information

Methotrexate is a cytotoxic agent that inhibits thymidylate synthetase and de novo purine synthesis. ......by AdooQ BioScience, LLC
Methotrexate, a folate antagonist, is a potent anti-inflammatory agent when used weekly in low concentrations, the anti-phlogistic action of which is due to increased adenosine release at inflamed sites. ......by BOC Sciences
Methotrexate is a traditional folate antagonist, with median IC50 of 78 nM for a 120 h drug exposure in a panel of six pediatric leukemia and lymphoma cell lines using the sulforhodamine B assay. ......by MedChemexpress Co., Ltd.
Methotrexate is an antimetabolite and antifolate agent with antineoplastic and immunosuppressant activities. Methotrexate binds to and inhibits the enzyme dihydrofolate reductase, resulting in inhibition of purine nucleotide and thymidylate synthesis and, subsequently, inhibition of DNA and RNA syntheses. Methotrexate also exhibits potent immunosuppressant activity although the mechanism(s) of actions is unclear. ......by MedKoo Biosciences, Inc.
Methotrexate (MTX), analog of folic acid, is a nonspecific inhibitor of the dihydrofolate reductase(DHFR) of bacteria and cancerous cells as well as normal cells. It forms an inactive ternary complex with DHFR and NADPH. ......by Selleck Chemicals LLC
Methotrexate, a folate antagonist, is a potent anti-inflammatory agent when used weekly in low concentrations, the anti-phlogistic action of which is due to increased adenosine release at inflamed sites. Studies have demonstrated that methotrexate polyglutamates are active inhibitors of several enzymatic reactions, including dihydrofolate reductase. ......by Target Molecule Corp.
Cytotoxic agent. Inhibits thymidylate synthetase and de novo purine synthesis. Potent folic acid antagonist; inhibits dihydrofolate reductase. Also inhibits Ras carboxyl methylation in DKOB8 cells, leading to decreased p44 and Akt activation. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Light yellow to yellow Solid EBNumber:EB000023198

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 90 mg/mL warming (198.04 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM); In vivo 30% PEG400+0.5% Tween80+5% Propylene glycol30 mg/mL by Selleck Chemicals LLC
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Methotrexate Bristol-Myers Squibb Co Rheumatoid arthritis 2013/4/30 2015/12/31 Phase 4 Clinical
Methotrexate Universita degli studi di Roma "La Sapienza" Crohns disease 2012/12/31 2015/12/31 Phase 4 Clinical
Methotrexate - Pre-registration
Methotrexate - Launched
7

Safety Data of Methotrexate

Hazard Symbols : T
Risk Statements : R61;R25;R36/38
Safety Statements : S53;S26;S36/37;S45
Transport Information : UN 1544
HS Code : 29335995
RTECS : MA1225000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
Abcam 10mg/USD45() USA
AdooQ BioScience, LLC USA
Alfa Chemistry USA
Apexbio Technology LLC USA
Arden (China) Pharmaceutical Chemical Co., Ltd. China
Ark Pharm, Inc. USA
BOC Sciences
Beijing Eagle Sky Pharmatech Co., Ltd. China
Beijing Lang Rebone Technology Co., Ltd. China
Biochempartner Co., Ltd China
CHEMSCENE, LLC 100mg/USD60();500mg/USD156() USA
Cayman Chemical Company 50mg/USD18() USA
Chemos GmbH Germany
Deqing Xinxi Plastic Chemical Co., Ltd. China
Hubie Xinyuanshun Pharm&Chem Co., Ltd. China
Indofine Chemical Company, Inc. USA
LKT Laboratories Inc. USA
Lianyungang Jinkang Pharmaceutical Technology Co., Ltd. China
MedChemexpress Co., Ltd. 100mg/USD60();500mg/USD156() USA
MedKoo Biosciences, Inc. 100mg/USD75();100g/USD2650() USA
Parling (Shanghai) PharmaTech Co., Ltd. China
Pure Chemistry Scientific Inc. 1g/USD51(In stock) USA
Santa Cruz Biotechnology, Inc. 100mg/USD79() USA
Selleck Chemicals LLC 10mM/1mLIn DMSO/USD134(In stock);100mg/USD147(In stock);200mg/USD220(In stock);500mg/USD470(In stock) USA
Sequoia Research Products Ltd.
Shandong Kingnod Pharmaceuticals Co., Ltd. China
Shanghai Haoyuan Chemexpress Co., Ltd. 100mg/USD60();500mg/USD156() China
Shanghai Jinhe Bio-Technology Co., Ltd. China
Shanghai Orient Chemical Co., Ltd. China
Spectrum Chemical Mfg. Corp. 1g/USD675() USA
Suzhou Sunray Pharmaceutical Co., Ltd. China
Suzhou Unite Pharmtech Co., Ltd. China
Target Molecule Corp. 10mg/USD24();50mg/USD43();100mg/USD84();500mg/USD126() USA
Tocris Bioscience Inc. 100mg/USD115() USA
Zhejiang Chemicals Import & Export Corporation China
10

Related Products

Other Forms of 59-05-2

Name CAS No Formula MW
Sodium methotrexate 7413-34-5 C20H20N8Na2O5 498.4

Recommended Compounds in Antifolate ADC Cytotoxin

Name CAS No Formula MW
Trimethoprim 738-70-5 C14H18N4O3 290.32
Calcium N5-methyltetrahydrofolate 26560-38-3 C20H23CaN7O6 497.52
Folinic acid 58-05-9 C20H23N7O7 473.44
Folinic acid (calcium salt pentahydrate) 6035-45-6 C20H21CaN7O7 511.5
Pemetrexed (disodium hemipenta hydrate) (1:2:2.5) 357166-30-4 C40H48N10Na4O17 1032.83
Pemetrexed (disodium) 150399-23-8 C20H19N5Na2O6 471.37
Levoleucovorin (Calcium) 80433-71-2 C20H21CaN7O7 511.5
Folinic acid (Calcium) 1492-18-8 C20H21CaN7O7 511.50144
Pyrimethamine 58-14-0 C12H13ClN4 248.71
Levomefolate (calcium) 151533-22-1 C40H48CaN14O12 956.97
Levomefolic acid 31690-09-2 C20H25N7O6 459.46
Pemetrexed 137281-23-3 C20H21N5O6 427.41
Pralatrexate 146464-95-1 C23H23N7O5 477.47
QN254 C17H18ClN5O2 359.81
P218 C18H24N4O4 360.41
P65 C14H15Cl3N4O2 377.65
WR99210 47326-86-3 C14H18Cl3N5O2 394.68
Pemetrexed (disodium) 150399-23-8 C20H19N5Na2O6 471.37429856
Levomefolate (calcium) 151533-22-1 C20H23CaN7O6 497.5179
Cycloguanil D6 C11H8D6ClN5 257.7523

Recommended Compounds in Same Indication

Name CAS No Formula MW
Vidofludimus 717824-30-1 C20H18FNO4 355.36
R406 (free base) 841290-80-0 C22H23FN6O5 470.45
R406 841290-81-1 C28H29FN6O8S 628.63
R788 901119-35-5 C23H26FN6O9P 580.46
R788 (disodium hexahydrate) 914295-16-2 C23H24FN6Na2O9P 624.42
Itacitinib 1334298-90-6 C26H23F4N9O 553.5142
PH-797804 586379-66-0 C22H19BrF2N2O3 477.3
ADL-5859 850173-95-4 C24H29ClN2O3 428.95
Tofacitinib 477600-75-2 C16H20N6O 312.37
6-Mercaptopurine 50-44-2 C5H4N4S 152.18
Mizoribine 50924-49-7 C9H13N3O6 259.22
MK-0812 624733-88-6 C24H34F3N3O3 469.54
Tofacitinib (citrate) 540737-29-9 C22H28N6O8 504.49
Firategrast 402567-16-2 C27H27F2NO6 499.5
IB-MECA 152918-18-8 C18H19IN6O4 510.2857
Rofecoxib 162011-90-7 C17H14O4S 314.36
Baricitinib 1187594-09-7 C16H17N7O2S 371.42
Duvelisib 1201438-56-3 C22H17ClN6O 416.863
AVL-292 1202757-89-8 C22H22FN5O3 423.44
Olmutinib 1353550-13-6 C26H26N6O2S 486.59
11

Route of Synthesis

12

References

13

More Information

Methotrexate

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