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7-Hydroxymethotrexate

Names

[ CAS No. ]:
5939-37-7

[ Name ]:
7-Hydroxymethotrexate

[Synonym ]:
7-hydroxy methotrexate

Biological Activity

[Description]:

7-Hydroxymethotrexate is a major metabolite of Methotrexate (MTX; HY-14519). Methotrexate, an antimetabolite and antifolate agent, inhibits the enzyme dihydrofolate reductase, thereby preventing the conversion of folic acid into tetrahydrofolate, and inhibiting DNA synthesis[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Inflammation/Immunology

[In Vitro]

7-Hydroxymethotrexate (7-OHMTX) has the affinity of DHFR markedly lower (>100-fold) than for Methotrexate (MTX) [1].

[In Vivo]

7-Hydroxymethotrexate (4 mg/kg; IV) has a terminal half-life of 97.2 min and a total clearance value of 9.6 mL/min•mg[1]. Animal Model: Male Wistar rats (270-440 g)[1] Dosage: 4 mg/kg (Pharmacokinetic Analysis) Administration: IV Result: Had a terminal half-life of 97.2 min and a total clearance value of 9.6 mL/min•mg.

[References]

[1]. L Fahrig, et al. Pharmacokinetics of methotrexate (MTX) and 7-hydroxymethotrexate (7-OH-MTX) in rats and evidence for the metabolism of MTX to 7-OH-MTX. Cancer Chemother Pharmacol. 1989;23(3):156-60.

[2]. Ping Guo, et al. Determination of methotrexate and its major metabolite 7-hydroxymethotrexate in mouse plasma and brain tissue by liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal. 2007 Apr 11;43(5):1789-95.

Chemical & Physical Properties

[ Density]:
1.68g/cm3

[ Melting Point ]:
230ºC dec.

[ Molecular Formula ]:
C20H22N8O6

[ Molecular Weight ]:
470.43900

[ Exact Mass ]:
470.16600

[ PSA ]:
230.77000

[ LogP ]:
1.52730

[ Index of Refraction ]:
1.76

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MA1000000
CHEMICAL NAME :
L-Glutamic acid, N-(4-(((2,4-diamino-1,7-dihydro-7-oxo-6-pteridinyl)me thyl)methylamino) benzoyl)-
CAS REGISTRY NUMBER :
5939-37-7
LAST UPDATED :
199712
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C20-H22-N8-O6

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CCPHDZ Cancer Chemotherapy and Pharmacology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1978- Volume(issue)/page/year: 37,415,1996

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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