Home Other Building Blocks 7-HYDROXY METHOTREXATE

7-HYDROXY METHOTREXATE

CAS No.:
5939-37-7
Catalog Number:
AG00E8VH
Molecular Formula:
C20H22N8O6
Molecular Weight:
470.4387
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Product Description
Catalog Number:
AG00E8VH
Chemical Name:
7-HYDROXY METHOTREXATE
CAS Number:
5939-37-7
Molecular Formula:
C20H22N8O6
Molecular Weight:
470.4387
MDL Number:
MFCD00674903
IUPAC Name:
2-[[4-[(2,4-diamino-7-oxo-8H-pteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
InChI:
InChI=1S/C20H22N8O6/c1-28(8-12-18(32)26-16-14(23-12)15(21)25-20(22)27-16)10-4-2-9(3-5-10)17(31)24-11(19(33)34)6-7-13(29)30/h2-5,11H,6-8H2,1H3,(H,24,31)(H,29,30)(H,33,34)(H5,21,22,25,26,27,32)
InChI Key:
HODZDDDNGRLGSI-UHFFFAOYSA-N
SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)N(Cc1nc2c(N)nc(nc2[nH]c1=O)N)C
NSC Number:
380962
Properties
Complexity:
830  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
470.166g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
470.446g/mol
Monoisotopic Mass:
470.166g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
226A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.8  
Literature
Title Journal
Simple and sensitive HPLC method for the fluorometric determination of methotrexate and its major metabolites in human plasma by post-column photochemical reaction. Biomedical chromatography : BMC 20120101
[Pharmacokinetic analysis of high-dose methotrexate treatments in children with hematologic malignancies]. Orvosi hetilap 20111002
The influence of 7-OH methotrexate metabolite on clinical relevance of methotrexate determination. Clinical laboratory 20110101
High-dose methotrexate in children with acute lymphoblastic leukemia: 7-hydroxymethotrexate systemic exposure and urinary concentrations at the steady state correlate well with those of methotrexate. Arzneimittel-Forschung 20100101
Abcc2 (Mrp2), Abcc3 (Mrp3), and Abcg2 (Bcrp1) are the main determinants for rapid elimination of methotrexate and its toxic metabolite 7-hydroxymethotrexate in vivo. Molecular cancer therapeutics 20091201
Methotrexate catabolism to 7-hydroxymethotrexate in rheumatoid arthritis alters drug efficacy and retention and is reduced by folic acid supplementation. Arthritis and rheumatism 20090801
Functionally overlapping roles of Abcg2 (Bcrp1) and Abcc2 (Mrp2) in the elimination of methotrexate and its main toxic metabolite 7-hydroxymethotrexate in vivo. Clinical cancer research : an official journal of the American Association for Cancer Research 20090501
Gene expression profiling of leukemia T-cells resistant to methotrexate and 7-hydroxymethotrexate reveals alterations that preserve intracellular levels of folate and nucleotide biosynthesis. Biochemical pharmacology 20090415
In vivo-in vitro relationship of methotrexate 7-hydroxylation by aldehyde oxidase in four different strain rats. Drug metabolism and pharmacokinetics 20061201
Interaction of methotrexate with organic-anion transporting polypeptide 1A2 and its genetic variants. The Journal of pharmacology and experimental therapeutics 20060801
Coadministration of lansoprazole and naproxen does not affect the pharmacokinetic profile of methotrexate in adult patients with rheumatoid arthritis. Journal of clinical pharmacology 20051001
Effects and interaction of 7-hydroxy methotrexate and methotrexate in leukaemic cells ex vivo measured by the thymidylate synthase inhibition assay. Cancer chemotherapy and pharmacology 20050901
Pharmacokinetic study of methotrexate following intra-articular injection of methotrexate loaded poly(L-lactic acid) microspheres in rabbits. Journal of pharmaceutical sciences 20050601
Interference of 7-hydroxymethotrexate with the determination of methotrexate in plasma samples from children with acute lymphoblastic leukemia employing routine clinical assays. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050325
Disparate mechanisms of antifolate resistance provoked by methotrexate and its metabolite 7-hydroxymethotrexate in leukemia cells: implications for efficacy of methotrexate therapy. Blood 20041215
Lumiracoxib does not affect methotrexate pharmacokinetics in rheumatoid arthritis patients. The Annals of pharmacotherapy 20041001
Combined oral cyclosporin and methotrexate therapy in patients with rheumatoid arthritis elevates methotrexate levels and reduces 7-hydroxymethotrexate levels when compared with methotrexate alone. Rheumatology (Oxford, England) 20030801
System approach to modeling metabolite formation from parent drug: a working example with methotrexate. Methods and findings in experimental and clinical pharmacology 20021001
Lack of pharmacokinetic interaction between rofecoxib and methotrexate in rheumatoid arthritis patients. Journal of clinical pharmacology 20011001
Separation of selected anticancer drugs using superheated water as the mobile phase. Analytical chemistry 20010815
No effect of phenobarbital pretreatment of rats on methotrexate pharmacokinetics in the isolated liver perfused in a single-pass way. Pharmacology 20010201
Acute hepatotoxicity after high-dose methotrexate administration to rats. Pharmacology & toxicology 19910801
Properties