Acetyl-D-methionine
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Acetyl-D-methionine

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Category
D-Amino Acids
Catalog number
BAT-003464
CAS number
1509-92-8
Molecular Formula
C7H13NO3S
Molecular Weight
191.20
Acetyl-D-methionine
IUPAC Name
(2R)-2-acetamido-4-methylsulfanylbutanoic acid
Synonyms
Ac-D-Met-OH; N-Acetyl-D-methionine
Purity
≥ 99% (HPLC)
Density
1.202±0.06 g/cm3(Predicted)
Melting Point
102-108 ºC
Boiling Point
453.6±40.0 °C(Predicted)
Storage
Store at RT
InChI
InChI=1S/C7H13NO3S/c1-5(9)8-6(7(10)11)3-4-12-2/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-/m1/s1
InChI Key
XUYPXLNMDZIRQH-ZCFIWIBFSA-N
Canonical SMILES
CC(=O)NC(CCSC)C(=O)O
1. The kinetics and dynamics of three kinds of radioactive methionine after i.v. administration in mice
E Hayama, N Motoji, A Shigematsu Eur J Drug Metab Pharmacokinet. 1991 Oct-Dec;16(4):287-97. doi: 10.1007/BF03189974.
In C57BL mice, a tracer amount of methionine (Met) at a concentration approximate to that in the blood was administered in the tail vein (i.v.). The rates of endogenous metabolic decomposition of methionine were obtained by using three specifically labelled compounds, [1-14C]-Met, [m-14C]-Met and [35S]-Met. Results on the kinetics and dynamics after i.v. administration suggested that 5 min after administration, most of the labelled compounds were taken up into the organs and tissues, and only a small portion was excreted in the expired air as CO2, the final metabolite of methionine. At 30 min the radioactive concentration in blood was minimal and was consistent with the maximum of the 14CO2 excretion in expired air. Gradual increase of the radioactive concentration in blood after 30 min might be due to the contribution of the metabolite in the blood. Methionine taken up was endogenously utilized by more than 40% during 48 h and it maintained the order of [1-14C]:[m-14C]:[35S]. Out of the remaining 60%, 40% was metabolized in 6 h after administration, the [1-14C] moiety being excreted mainly into expired air, the [m-14C] moiety into expired air and urine, and the [35S] moiety mainly into urine and partly into faeces. Microautoradiograms revealed that a part of the last 20% was taken up into the enzyme proteins contained in the pancreatic juice and intestinal juice, and was decomposed within 48 h.
2. Metabolism of [14C]- and [35S]S-(1,2-dichlorovinyl)-L-cysteine in the male Fischer 344 rat
M B Finkelstein, N J Patel, M W Anders Drug Metab Dispos. 1995 Jan;23(1):124-8.
The metabolic fate, tissue distribution, and elimination profile of [35S]- and [cysteine-U-14C]S-(1,2-dichlorovinyl)-L-cysteine (DCVC)--given either intravenously or intraperitoneally to male Fischer 344 rats--was investigated. Blood samples were collected periodically from 5 min to 96 hr after administration. More than 99% of the DCVC was cleared from plasma within 2.5 hr after either intravenous or intraperitoneal injection. The initial half-lives of both [35S]- and [14C]DCVC were 2.0 and 2.8 hr, respectively, and the mercapturate S-(1,2-dichlorovinyl)-N-acetyl-L-cysteine was detected in plasma within 5 min of giving DCVC. The major plasma metabolite detected after giving [35S]DCVC was inorganic sulfate, and S-(1,2-dichlorovinyl)-N-acetyl-L-cysteine and pyruvate were also detected in plasma after giving [14C]DCVC. S-(1,2-Dichlorovinyl)-N-acetyl-L-cysteine was the major urinary metabolite detected after giving [14C]DCVC, and inorganic sulfate was excreted in the urine after giving [35S]DCVC. Administration of the cysteine conjugate beta-lyase inhibitor aminooxyacetic acid led to a significant increase in the urinary excretion of radioactivity, mostly in the form of the mercapturate. The kidney contained the highest amount of radioactivity after administration of [35S]DCVC. In addition, similar amounts of radioactivity were present in brain, heart, kidney, and liver after administration of [14C]DCVC, but the 14C content of the liver was decreased in aminooxyacetic acid-treated rats. This study shows that DCVC is rapidly metabolized to inorganic sulfate and S-(1,2-dichlorovinyl)-N-acetyl-L-cysteine, which are eliminated in the urine.
3. Absorption, distribution, metabolism, and excretion of N,N-diethyl-M-toluamide in the rat
G P Schoenig, R E Hartnagel Jr, T G Osimitz, S Llanso Drug Metab Dispos. 1996 Feb;24(2):156-63.
This study was conducted to evaluate the pharmacokinetic parameters of absorption, distribution, metabolism, and excretion (ADME) of the personal insect repellent N,N-diethyl-m-toluamide (DEET) after oral or dermal administration of [14C]DEET in the rat. Six experiments were conducted using separate groups, each consisting of five male and five female rats. Three experiments involved the determination of ADME patterns after oral administration of [14C]DEET as: 1) a single low dose (100 mg DEET/kg body weight); 2) a single high dose (500 mg DEET/kg body weight); and 3) a repeated low dose (100 mg DEET/kg body weight daily for 14 days). A fourth experiment involved the determination of ADME patterns after dermal administration of [14C]DEET at a single low dose of 100 mg DEET/kg body weight. In these four experiments, urine and feces were collected over a 7-day posttreatment period, after which time the animals were euthanized and selected tissues and organs were harvested. Urine, feces, and tissues were analyzed for total 14C content. The major urinary metabolites were identified, and the urinary metabolic profile for each dosage regimen was determined. The remaining two experiments examined the distribution of radioactivity in tissues of animals euthanized at peak 14C blood levels after receiving a single oral low dose or a dermal low dose. In the three experiments designed to determine the ADME patterns of DEET after oral administration, 85-91% of the administered radioactivity was found in the urine and 3-5% was found in the feces. The overall quantitative pattern of excretion of radioactivity into the urine and feces was similar for males and females in the three groups; however, the rate at which the radioactivity was excreted into the urine differed noticeably between individual oral dosing regimens. The fastest rate was observed in the repeated oral low-dose group, followed by the single oral low-dose and the single oral high-dose groups. In the group of rats that received the dermal low dose, 74-78% of the administered dose was found in the urine and 4-7% was found in the feces. An additional 6.5% was found on the surface of the skin at the application site or in association with the occlusive enclosure. The rate of absorption and subsequent excretion of administered radioactivity into the urine and feces was much slower after dermal administration than after all oral dosing regimens. Total tissue residues of 14C activity at 7 days ranged from 0.15 to 0.67% of the administered dose for all dosage regimens. At peak 14C blood levels, the percentages of administered dose reaching the systemic circulation and total 14C tissue residues were significantly higher in the group of animals administered [14C]DEET orally vs. the animals administered [14C]DEET by the dermal route of administration. In both cases, the only tissues with 14C residues consistently higher than that of plasma were the liver, kidney, and fat. HPLC analysis of urine from rats in the ADME phase of the study showed that DEET was metabolized completely in all treatment groups, with little or no parent compound excreted in the urine. Two major urinary metabolites were identified by mass spectroscopy. In both metabolites, the aromatic methyl substituent in the DEET molecule was oxidized to a carboxylic acid moiety. One of the metabolites also had undergone N-dealkylation of an ethyl substituent on the amide moiety.
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