(±)-Methotrexate
(±)-Methotrexate ((±)-Amethopterin; (±)-CL14377; (±)-WR19039) is the racemate of Methotrexate (HY-14519). Methotrexate is an orally active antifolate (Antifolate). Methotrexate inhibits dihydrofolate reductase (DHFR), blocks tetrahydrofolate production, suppresses purine/pyrimidine synthesis and transmethylation, and causes intracellular accumulation of AICAR. Methotrexate promotes extracellular adenosine release, regulates the cytokine network, and inhibits the alarmin function of HMGB1. Methotrexate induces apoptosis and cytotoxicity, upregulates the expression of iNOS and COX-2, suppresses hippocampal neurogenesis, and induces pulmonary fibrosis. Methotrexate is used in the research of various immune and inflammation-related diseases such as arthritis, psoriasis, systemic lupus erythematosus, as well as pulmonary fibrosis and breast cancer.
For research use only. We do not sell to patients.
- CAS No.: 60388-53-6
- Formula: C20H22N8O5
- Molecular Weight:454.44
-
Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
Biological Activity
|
COX-2 |
IL-8 |
iNOS |
(±)-Methotrexate is the racemate of Methotrexate (HY-14519), Methotrexate at high concentrations stimulates adenosine secretion of endothelial cells, fibroblasts and peripheral blood monocytes, and this effect is amplified under metabolic stress; it further modulates macrophage function through adenosine and suppresses peripheral blood mononuclear cells from producing immunoglobulins, rheumatoid factors and spontaneous IL-8, which may be attributed to the reduction of intracellular polyamine levels[1].
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (MTX) (0.01-100 μM; 72 h) induces dose-dependent cytotoxicity in primary mouse alveolar epithelial cells (MAEC) and primary mouse lung fibroblasts (MLF)[4].
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (1 μM; 12-48 h) induces significant time-dependent apoptosis in primary mouse alveolar epithelial cells (MAEC), but exerts no significant pro-apoptotic effect on primary mouse lung fibroblasts (MLF) under the same conditions[4].
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (0.5-5 μM; 24 h) dose-dependently enhances cytotoxicity and reduces cell viability in FM3A breast cancer cells[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (3 mg/kg; p.o.; daily; days 21-35) induces pulmonary fibrosis in male C57BL/6J mice in a time-dependent manner[4].
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (40 mg/kg; i.p.; single dose) induces hippocampal dysfunction in both FM3A-inoculated breast cancer mice and tumor-free healthy mice, including significant depression-like behaviors, cognitive impairment, reduced hippocampal neurogenesis, and upregulated expression of pro-inflammatory enzymes[5].
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (MTX) (2 mg/kg; i.p.; once weekly for 5 consecutive weeks) is effective against Freund's complete adjuvant-induced arthritis[6].
(±)-Methotrexate is the racemate of Methotrexate, Methotrexate (1 mg/kg, intraperitoneal injection, once a week for 5 weeks) combined with Curcumin (HY-N0005, 30 mg/kg and 100 mg/kg, intraperitoneal injection, three times a week for 5 weeks) exhibits remarkable anti-arthritic effects and protective activity against hematotoxicity[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
-
CAS No. 60388-53-6
-
Appearance Solid
-
Molecular Weight 454.44
-
Formula C20H22N8O5
-
SMILES
O=C(C(CCC(O)=O)NC(C1=CC=C(C=C1)N(C)CC2=NC3=C(N=C(N=C3N=C2)N)N)=O)O
-
Synonyms
(±)-Amethopterin; (±)-CL14377; (±)-WR19039
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Purity & Documentation
-
Data Sheet (272 KB)
-
SDS (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
-
Handling Instructions (2659 KB)
References
[1]. Cronstein BN, et al. The mechanism of action of methotrexate. Rheumatic diseases clinics of North America. 1997 Nov;23(4):739-55. [Content Brief]
[2]. Bedoui Y, et al. Methotrexate an Old Drug with New Tricks. International journal of molecular sciences. 2019 Oct 10;20(20):5023. [Content Brief]
[4]. Ohbayashi M, et al. Induction of pulmonary fibrosis by methotrexate treatment in mice lung in vivo and in vitro. The Journal of toxicological sciences. 2010 Oct;35(5):653-61. [Content Brief]
[5]. Yang M, et al. Acute treatment with methotrexate induces hippocampal dysfunction in a mouse model of breast cancer. Brain research bulletin. 2012 Oct 01;89(1-2):50-6. [Content Brief]
[6]. Banji D, et al. Evaluation of the concomitant use of methotrexate and curcumin on Freund's complete adjuvant-induced arthritis and hematological indices in rats. Indian J Pharmacol. 2011 Sep;43(5):546-50. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
- (±)-Methotrexate
- 60388-53-6
- (±)-Amethopterin
- (±)-CL14377
- (±)-WR19039
- Antifolate
- Dihydrofolate reductase (DHFR)
- NO Synthase
- COX
- Interleukin Related
- Drug Isomer
- tetrahydrofolate
- AICAR transformylase
- ROS
- COX-2
- iNOS
- HMGB1 alarmin
- purine/pyrimidine synthesis
- dihydrofolate reductase
- methotrexate-polyglutamates
- leukotriene B4
- Inhibitor
- inhibitor
- inhibit