About: Aminopterin     Goto   Sponge   NotDistinct   Permalink

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http://linked.open...gbank/description
  • Aminopterin is an amino derivative of folic acid, which was once used as an antineoplastic agent in the treatment of pediatric leukemia. In the 1950's its production was discontinued in favor of methotrexate, which is less potent but less toxic. Off label, aminopterin has also been used in the treatment of psoriasis. Clinicians need to be aware of the characteristic teratologic effects of aminopterin and methotrexate. (en)
http://linked.open...generalReferences
  • # Aftimos S: Fetal methotrexate/aminopterin syndrome in an adult: a likely case with ectodermal abnormalities. Clin Dysmorphol. 2009 Jan;18(1):53-5. doi: 10.1097/MCD.0b013e32831552c4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19011571 # Wheeler M, O'Meara P, Stanford M: Fetal methotrexate and misoprostol exposure: the past revisited. Teratology. 2002 Aug;66(2):73-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12210010 # NICHOL CA, WELCH AD: On the mechanism of action of aminopterin. Proc Soc Exp Biol Med. 1950 Jun;74(2):403-11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15440837 # 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":http://www.ncbi.nlm.nih.gov/pubmed/22653877 # 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":http://www.ncbi.nlm.nih.gov/pubmed/16299240 (en)
http://linked.open...gy/drugbank/group
  • withdrawn (en)
  • investigational (en)
http://linked.open...ugbank/indication
  • Prior to its withdrawal, aminopterin was initially used in the treatment of childhood leukemia; specifically to induce remissions. Later, aminopterin was used off-label in the United States to treat psoriasis, yielding dramatic lesion clearing. Aminopterin was later supplanted by methotrexate for treating cancer because of its better therapeutic index. Aminopterin (as well as methotrexate) has also been explored for use as an abortifacient. However, their association with severe congenital malformations and teratogenic effects have become known as fetal aminopterin syndrome. (en)
sameAs
Title
  • Aminopterin (en)
adms:identifier
http://linked.open...mechanismOfAction
  • Aminopterin is an amino derivative of folic acid which binds competitively to the dihydrofolate reductase enzyme to block tetrahydrofolate synthesis. Tetrahydrofolate is essential in the production of purines and pyrimadines, thus it's deficiency results in a reduction of DNA, RNA and protein synthesis. (en)
http://linked.open.../drugbank/synonym
  • 4'-Amino-folsaeure (en)
  • 4-amino-4-deoxypteroylglutamate (en)
  • 4-amino-PGA (en)
  • 4-aminofolic acid (en)
  • 4-aminopteroylglutamic acid (en)
  • A-Ninopterin (en)
  • A-ninopterin (en)
  • APGA (en)
  • Aminopteridine (en)
  • Aminopterine (en)
  • Minopterin (en)
  • Pteramina (en)
  • N-(4-{[(2,4-Diamino-6-pteridinyl)methyl]amino}benzoyl)glutamic acid (en)
http://linked.open...ynthesisReference
http://linked.open...ugbank/IUPAC-Name
http://linked.open...gy/drugbank/InChI
http://linked.open...Molecular-Formula
http://linked.open.../Molecular-Weight
http://linked.open...noisotopic-Weight
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http://linked.open.../Water-Solubility
http://linked.open...ogy/drugbank/logP
http://linked.open...ogy/drugbank/logS
http://linked.open...logy/drugbank/pKa
http://linked.open...nd-Acceptor-Count
http://linked.open...-Bond-Donor-Count
http://linked.open...drugbank/InChIKey
http://linked.open...urface-Area--PSA-
http://linked.open...nk/Polarizability
http://linked.open...bank/Refractivity
http://linked.open...atable-Bond-Count
http://linked.open...casRegistryNumber
  • 54-62-6 (en)
http://linked.open...drugbank/category
  • (en)
http://linked.open...k/Bioavailability
http://linked.open...bank/Ghose-Filter
http://linked.open...nk/MDDR-Like-Rule
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http://linked.open...k/Number-of-Rings
http://linked.open...siological-Charge
http://linked.open...bank/Rule-of-Five
http://linked.open...tional-IUPAC-Name
http://linked.open...strongest-acidic-
http://linked.open...-strongest-basic-
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