MedKoo Cat#: 597208 | Name: Aminopterin sodium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aminopterin sodium is an antineoplastic drug with immunosuppressive properties often used in chemotherapy. Aminopterin is a synthetic derivative of pterin. Aminopterin works as an enzyme inhibitor by competing for the folate binding site of the enzyme dihydrofolate reductase. Its binding affinity for dihydrofolate reductase effectively blocks tetrahydrofolate synthesis. This results in the depletion of nucleotide precursors and inhibition of DNA, RNA, and protein synthesis.

Chemical Structure

Aminopterin sodium
Aminopterin sodium
CAS#58602-66-7 (sodium)

Theoretical Analysis

MedKoo Cat#: 597208

Name: Aminopterin sodium

CAS#: 58602-66-7 (sodium)

Chemical Formula: C19H19N8NaO5

Exact Mass:

Molecular Weight: 462.40

Elemental Analysis: C, 49.35; H, 4.14; N, 24.23; Na, 4.97; O, 17.30

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Synonym
Aminopterin sodium; NSC 739 [as the base]; 4-Aminopteroylglutamic acid sodium salt; NSC-739; NSC739;
IUPAC/Chemical Name
sodium (S)-4-carboxy-2-(4-(((2,4-diaminopteridin-6-yl)methyl)amino)benzamido)butanoate
InChi Key
CJNYIGNPSQIZPJ-YDALLXLXSA-M
InChi Code
InChI=1S/C19H20N8O5.Na/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29;/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27);/q;+1/p-1/t12-;/m0./s1
SMILES Code
O=C(O)CC[C@@H](C([O-])=O)NC(C1=CC=C(NCC2=NC3=C(N)N=C(N)N=C3N=C2)C=C1)=O.[Na+]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 462.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ren Z, Yu L, Xie M, Liang Y, Zhu F, Huang R, Zhang Z, Fu C. Successful treatment of multisite hemorrhage by several methods in brain metastasis of choriocarcinoma: A case report. Medicine (Baltimore). 2018 May;97(21):e10794. doi: 10.1097/MD.0000000000010794. PubMed PMID: 29794762. 2: Tobias AM, Toska D, Lange K, Eck T, Bhat R, Janson CA, Rotella DP, Gubler U, Goodey NM. Expression, purification, and inhibition profile of dihydrofolate reductase from the filarial nematode Wuchereria bancrofti. PLoS One. 2018 May 22;13(5):e0197173. doi: 10.1371/journal.pone.0197173. eCollection 2018. PubMed PMID: 29787565; PubMed Central PMCID: PMC5963757. 3: Fu LP. Therapeutic approach for the cesarean scar pregnancy. Medicine (Baltimore). 2018 May;97(18):e0476. doi: 10.1097/MD.0000000000010476. PubMed PMID: 29718837. 4: Del Rosario M, Tsai H, Dasanu CA. Durable Complete Response of Primary CNS Lymphoma in an 80-Year-Old Patient with Retroviral Infection. Conn Med. 2017 Apr;81(4):223-226. PubMed PMID: 29714407. 5: Matsumoto K, Akiyama M, Kajio N, Otomo K, Suzuki K, Nishina N, Kasuya K, Oishi N, Kameyama K, Takeuchi T. Adolescent PR3-ANCA-positive hypertrophic pachymeningitis: A case report and review of the literature. Medicine (Baltimore). 2018 Apr;97(17):e0521. doi: 10.1097/MD.0000000000010521. PubMed PMID: 29703022; PubMed Central PMCID: PMC5944515. 6: Haydaroglu Sahin H, Mete A, Pehlivan M. Neurolymphomatosis in non-Hodgkin lymphoma with cranial multineuritis: A case report. Medicine (Baltimore). 2018 Apr;97(15):e0303. doi: 10.1097/MD.0000000000010303. PubMed PMID: 29642156; PubMed Central PMCID: PMC5908615. 7: Azevedo PO, Castellen NR, Salai AF, Barbosa FS, Alves CAXM, Pinto CAL. Panniculitis associated with amyopathic dermatomyositis. An Bras Dermatol. 2018 Jan-Feb;93(1):119-121. doi: 10.1590/abd1806-4841.20186597. PubMed PMID: 29641712; PubMed Central PMCID: PMC5871377. 8: Peiró Cadahía J, Bondebjerg J, Hansen CA, Previtali V, Hansen AE, Andresen TL, Clausen MH. Synthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis. J Med Chem. 2018 Apr 26;61(8):3503-3515. doi: 10.1021/acs.jmedchem.7b01775. Epub 2018 Apr 10. PubMed PMID: 29605999. 9: Płusa T. [Advances in differential diagnosis and treatment of patients with sarcoidosis]. Pol Merkur Lekarski. 2018 Mar 27;44(261):135-138. Review. Polish. PubMed PMID: 29601563. 10: Xie J, Fan Z, Li Y, Zhang Y, Yu F, Su G, Xie L, Hou Z. Design of pH-sensitive methotrexate prodrug-targeted curcumin nanoparticles for efficient dual-drug delivery and combination cancer therapy. Int J Nanomedicine. 2018 Mar 9;13:1381-1398. doi: 10.2147/IJN.S152312. eCollection 2018. PubMed PMID: 29563794; PubMed Central PMCID: PMC5849920. 11: Alagbe OA, Adeniyi TO, Abayomi OA, Onifade EO. Interstitial ectopic pregnancy: a case report. Pan Afr Med J. 2017 Oct 11;28:135. doi: 10.11604/pamj.2017.28.135.13889. eCollection 2017. PubMed PMID: 29541285; PubMed Central PMCID: PMC5847127. 12: Alemao E, Johal S, Al MJ, Rutten-van Mölken M. Cost-Effectiveness Analysis of Abatacept Compared with Adalimumab on Background Methotrexate in Biologic-Naive Adult Patients with Rheumatoid Arthritis and Poor Prognosis. Value Health. 2018 Feb;21(2):193-202. doi: 10.1016/j.jval.2017.05.020. Epub 2017 Jul 1. PubMed PMID: 29477401. 13: Manfredi A, Sebastiani M, Cassone G, Colaci M, Sandri G, Ferri C. Tocilizumab for the treatment of patients with rheumatoid arthritis and interstitial lung diseases: a case series. Clin Exp Rheumatol. 2018 Mar-Apr;36(2):342. Epub 2018 Feb 14. PubMed PMID: 29465372. 14: van Pelt PA, Dolhain RJEM, Kruize AA, Ammerlaan JJW, Hazes JW, Bijlsma JWJ, Wulffraat NM. Disease activity and dropout in young persons with juvenile idiopathic arthritis in transition of care: a longitudinal observational study. Clin Exp Rheumatol. 2018 Jan-Feb;36(1):163-168. Epub 2018 Jan 31. PubMed PMID: 29461957. 15: Kawami M, Harabayashi R, Harada R, Yamagami Y, Yumoto R, Takano M. Folic acid prevents methotrexate-induced epithelial-mesenchymal transition via suppression of secreted factors from the human alveolar epithelial cell line A549. Biochem Biophys Res Commun. 2018 Feb 26;497(1):457-463. doi: 10.1016/j.bbrc.2018.02.111. Epub 2018 Feb 13. PubMed PMID: 29448106. 16: Cline A, Jorizzo JL. Does daily folic acid supplementation reduce methotrexate efficacy? Dermatol Online J. 2017 Nov 15;23(11). pii: 13030/qt4hf5v2vk. PubMed PMID: 29447631. 17: Zhu Z, Shu X, Long S, Jiang X, Lu N, Zhu X, Liao W. Ulcerative colitis followed by the development of typical intestinal Behçet disease: A case report. Medicine (Baltimore). 2018 Feb;97(7):e9882. doi: 10.1097/MD.0000000000009882. PubMed PMID: 29443756; PubMed Central PMCID: PMC5839857. 18: Gao J, Li X, Chen J, Gong W, Yue K, Wu Z. Uterine artery embolization combined with local infusion of methotrexate and 5- fluorouracil in treating ectopic pregnancy: A CONSORT-compliant article. Medicine (Baltimore). 2018 Feb;97(5):e9722. doi: 10.1097/MD.0000000000009722. PubMed PMID: 29384854; PubMed Central PMCID: PMC5805426. 19: Jiang ZG, Winocur G, Wojtowicz JM, Shevtsova O, Fuller S, Ghanbari HA. PAN-811 prevents chemotherapy-induced cognitive impairment and preserves neurogenesis in the hippocampus of adult rats. PLoS One. 2018 Jan 25;13(1):e0191866. doi: 10.1371/journal.pone.0191866. eCollection 2018. PubMed PMID: 29370277; PubMed Central PMCID: PMC5785016. 20: Dong R, Ji J, Liu H, Wang J, He X. Primary spinal mucosa-associated lymphoid tissue lymphoma: A case report. Medicine (Baltimore). 2018 Jan;97(4):e9329. doi: 10.1097/MD.0000000000009329. Review. PubMed PMID: 29369169; PubMed Central PMCID: PMC5794353.