Aminopterin | CAS#54-62-6 | folic acid derivative | dihydrofolate reductase inhibitor

MedKoo Cat#: 540013 | Name: Aminopterin

Description:

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

Aminopterin is a folic acid derivative used as a rodenticide that has been shown to be teratogenic, and a dihydrofolate reductase inhibitor used to treat rheumatoid arthritis and leukemia.

Chemical Structure

Aminopterin

CAS#54-62-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 540013

Name: Aminopterin

CAS#: 54-62-6 (free acid)

Chemical Formula: C19H20N8O5

Exact Mass: 440.1557

Molecular Weight: 440.42

Elemental Analysis: C, 51.82; H, 4.58; N, 25.44; O, 18.16

Price and Availability

Size	Price	Availability
10mg	USD 110.00	Ready to ship
25mg	USD 225.00	Ready to ship
50mg	USD 385.00	Ready to ship
100mg	USD 650.00	Ready to ship
250mg	USD 1,350.00	Ready to ship

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Related CAS #

58602-66-7 (sodium) 54-62-6 (free acid)

Synonym

Aminopterinum; APGA; BRN 0069045; CCRIS 5856; ENT 26079; BRN0069045; CCRIS5856; ENT26079; BRN-0069045; CCRIS-5856; ENT-26079

IUPAC/Chemical Name

(4-(((2,4-diaminopteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid

InChi Key

TVZGACDUOSZQKY-LBPRGKRZSA-N

InChi Code

InChI=1S/C19H20N8O5/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)/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

Appearance

Yellow 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

>2 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

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#A9T08K05

QC Data

View QC data: current batch, Lot#A9T08K05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 440.42 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.

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

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PubMed PMID: 2016722. 5: Menter A, Thrash B, Cherian C, Matherly LH, Wang L, Gangjee A, Morgan JR, Maeda DY, Schuler AD, Kahn SJ, Zebala JA. Intestinal transport of aminopterin enantiomers in dogs and humans with psoriasis is stereoselective: evidence for a mechanism involving the proton-coupled folate transporter. J Pharmacol Exp Ther. 2012 Sep;342(3):696-708. doi: 10.1124/jpet.112.195479. Epub 2012 May 31. PubMed PMID: 22653877; PubMed Central PMCID: PMC3422524. 6: Piggott KD, Sorbello A, Riddle E, DeCampli W. Congenital cardiac defects: a possible association of aminopterin syndrome and in utero methotrexate exposure? Pediatr Cardiol. 2011 Apr;32(4):518-20. doi: 10.1007/s00246-011-9913-z. Epub 2011 Feb 17. PubMed PMID: 21327892. 7: Norris RE, Adamson PC. Clinical potency of methotrexate, aminopterin, talotrexin and pemetrexed in childhood leukemias. Cancer Chemother Pharmacol. 2010 May;65(6):1125-30. doi: 10.1007/s00280-009-1120-8. Epub 2009 Sep 27. PubMed PMID: 19784838. 8: Fehlner PF, Bencsath A, Lam T, King TP. The photodecomposition of aminopterin. J Immunol Methods. 1987 Jul 16;101(1):141-5. PubMed PMID: 3611791. 9: Vlahov IR, You F, Santhapuram HK, Wang Y, Vaughn JF, Hahn SJ, Kleindl PJ, Fan M, Leamon CP. Design and regioselective synthesis of a new generation of targeted therapeutics. Part 3: Folate conjugates of aminopterin hydrazide for the treatment of inflammation. Bioorg Med Chem Lett. 2011 Feb 15;21(4):1202-5. doi: 10.1016/j.bmcl.2010.12.085. Epub 2010 Dec 22. PubMed PMID: 21236665. 10: Lu Y, Stinnette TW, Westrick E, Klein PJ, Gehrke MA, Cross VA, Vlahov IR, Low PS, Leamon CP. Treatment of experimental adjuvant arthritis with a novel folate receptor-targeted folic acid-aminopterin conjugate. Arthritis Res Ther. 2011 Apr 4;13(2):R56. doi: 10.1186/ar3304. PubMed PMID: 21463515; PubMed Central PMCID: PMC3132048. 11: Gooptu M, Rhoades R, Pro B. Current management of peripheral T-cell lymphomas. Cancer Treat Res. 2015;165:289-303. doi: 10.1007/978-3-319-13150-4_12. Review. PubMed PMID: 25655615. 12: Krajewska-Walasek M. Aminopterin Syndrome Sine Aminopterin (ASSA) syndrome in two siblings: further delineation of the syndrome and review of the literature. Genet Couns. 1994;5(4):345-55. Review. PubMed PMID: 7888136. 13: Stone SR, Montgomery JA, Morrison JF. Inhibition of dihydrofolate reductase from bacterial and vertebrate sources by folate, aminopterin, methotrexate and their 5-deaza analogues. Biochem Pharmacol. 1984 Jan 15;33(2):175-9. PubMed PMID: 6367748. 14: Sirotnak FM, DeGraw JI, Moccio DM, Samuels LL, Goutas LJ. New folate analogs of the 10-deaza-aminopterin series. Basis for structural design and biochemical and pharmacologic properties. Cancer Chemother Pharmacol. 1984;12(1):18-25. PubMed PMID: 6690069. 15: Cocco L, Groff JP, Temple C Jr, Montgomery JA, London RE, Matwiyoff NA, Blakley RL. Carbon-13 nuclear magnetic resonance study of protonation of methotrexate and aminopterin bound to dihydrofolate reductase. Biochemistry. 1981 Jul 7;20(14):3972-8. PubMed PMID: 7284303. 16: Sirotnak FM, DeGraw JI, Schmid FA, Goutas LJ, Moccio DM. New folate analogs of the 10-deaza-aminopterin series. Further evidence for markedly increased antitumor efficacy compared with methotrexate in ascitic and solid murine tumor models. Cancer Chemother Pharmacol. 1984;12(1):26-30. PubMed PMID: 6690070. 17: Advani RH, Ansell SM, Lechowicz MJ, Beaven AW, Loberiza F, Carson KR, Evens AM, Foss F, Horwitz S, Pro B, Pinter-Brown LC, Smith SM, Shustov AR, Savage KJ, Vose JM. A phase II study of cyclophosphamide, etoposide, vincristine and prednisone (CEOP) Alternating with Pralatrexate (P) as front line therapy for patients with peripheral T-cell lymphoma (PTCL): final results from the T- cell consortium trial. Br J Haematol. 2016 Feb;172(4):535-44. doi: 10.1111/bjh.13855. Epub 2015 Dec 2. PubMed PMID: 26627450. 18: Cole PD, Drachtman RA, Smith AK, Cate S, Larson RA, Hawkins DS, Holcenberg J, Kelly K, Kamen BA. Phase II trial of oral aminopterin for adults and children with refractory acute leukemia. Clin Cancer Res. 2005 Nov 15;11(22):8089-96. PubMed PMID: 16299240; PubMed Central PMCID: PMC2906753. 19: Gubner R. Effect of "aminopterin" on epithelial tissues. Arch Dermatol. 1983 Jun;119(6):513-24. PubMed PMID: 6859892. 20: Tedeschi PM, Kathari YK, Johnson-Farley N, Bertino JR. Methylthioadenosine phosphorylase (MTAP)-deficient T-cell ALL xenografts are sensitive to pralatrexate and 6-thioguanine alone and in combination. Cancer Chemother Pharmacol. 2015 Jun;75(6):1247-52. doi: 10.1007/s00280-015-2747-2. Epub 2015 Apr 28. PubMed PMID: 25917288; PubMed Central PMCID: PMC4441744.