Cycloserin Produkt Beschreibung

D-Cycloserine Struktur
68-41-7
  • CAS-Nr.68-41-7
  • Bezeichnung:Cycloserin
  • Englisch Name:D-Cycloserine
  • Synonyma:Cycloserin
    pa94;106-7;NJ-21;PA 94;I-1431;Closina;E-733-A;Cyclorin;Closerin;Oxymycin
  • CBNumber:CB9138759
  • Summenformel:C3H6N2O2
  • Molgewicht:102.09
  • MOL-Datei:68-41-7.mol
Cycloserin physikalisch-chemischer Eigenschaften
  • Schmelzpunkt: :147 °C (dec.)(lit.)
  • alpha  :111 º (C=5, 2N NaOH)
  • Siedepunkt: :191.38°C (rough estimate)
  • Dichte :1.3516 (rough estimate)
  • Brechungsindex :1.5110 (estimate)
  • storage temp.  :−20°C
  • Löslichkeit :water: soluble50mg/mL, clear, colorless to light yellow
  • pka :pKa 4.5 (Uncertain)
  • Aggregatzustand :powder
  • Farbe :white to off-white
  • Optische Aktivität :[α]20/D +115.0±5.0°, c = 2% in H2O
  • Wasserlöslichkeit :SOLUBLE
  • Sensitive  :Air Sensitive
  • Merck  :14,2751
  • BRN  :80798
  • CAS Datenbank :68-41-7(CAS DataBase Reference)
  • NIST chemische Informationen :Cycloserine(68-41-7)
Sicherheit

D-Cycloserine Chemische Eigenschaften,Einsatz,Produktion Methoden

  • R-Sätze Betriebsanweisung: R5:Beim Erwärmen explosionsfähig.
    R20:Gesundheitsschädlich beim Einatmen.
  • S-Sätze Betriebsanweisung: S38:Bei unzureichender Belüftung Atemschutzgerät anlegen.
    S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
    S24/25:Berührung mit den Augen und der Haut vermeiden.
  • Chemische Eigenschaften White to pale yellow cryst. powder
  • Verwenden antibacterial (tuberculostatic)
  • Verwenden D-Cycloserine inhibits cell wall biosynthesis (D-Ala peptide bond formation). D-Cycloserine also prevents conversion of D-Ala to L-Ala. D-Cycloserine is an bacteriostatic. D-Cycloserine is an antibiot ic against Gram-negative bacteria.
  • Indications Cycloserine is a broad-spectrum antibiotic produced by Streptomyces orchidaceus. It is structural analogue of Dalanine and acts through a competitive inhibition of the D-alanine that is involved in bacterial cell wall synthesis. Cycloserine is inhibitory to M. tuberculosis and active against Escherichia coli, S. aureus, and Enterococcus, Nocardia, and Chlamydia spp. It is used in the treatment of MDR tuberculosis and is useful in renal tuberculosis, since most of the drug is excreted unchanged in the urine.
  • Trademarks Seromycin (Lilly).
  • Pharmazeutische Anwendungen A fermentation product of Strep. orchidaceus and other related organisms now produced synthetically. Aqueous solutions are stable at pH 7.8 but the agent is rapidly destroyed in acid conditions. It is active against a wide range of Gram-negative and Grampositive bacteria, including Staphylococcus aureus, streptococci, including Enterococcus faecalis, various enterobacteria, Nocardia and Chlamydia spp. M. tuberculosis is inhibited by 8–16 mg/L. Some environmental mycobacteria, including M. avium, are also susceptible. Its action is specifically antagonized by d-alanine, from which media for in-vitro tests should be free. Its use is limited by neurological and psychiatric side effects. Primary resistance in M. tuberculosis is rare and develops only slowly in patients treated with cycloserine alone. Its inclusion in combinations deters the development of resistance to other drugs. There is no cross-resistance with other therapeutic antibiotics.
    It is well absorbed when given orally, achieving a concentration of c. 10 mg/L 3–4 h after a 250 mg dose. Doubling the dose approximately doubles the plasma level. Some accumulation occurs over the first 3 or 4 days of treatment. In children receiving 20 mg/kg orally, plasma levels of 20–35 mg/L have been found. It is widely distributed throughout the body fluids, including the CSF. About 50% is excreted unchanged in the glomerular filtrate over 24 h and 65–70% over the subsequent 2 days. The remainder is metabolized. There is no tubular secretion and no effect of probenecid. Cycloserine accumulates in renal failure, reaching toxic levels if dosage is uncontrolled. It can be removed by hemodialysis.
    Evidence of central nervous system toxicity, including headache, somnolence, vertigo, visual disturbances, confusion, depression, acute psychotic reactions and tremors, may develop over the first 2 weeks of treatment. The effects may be exacerbated by alcohol and can be reduced, to some extent, by administering pyridoxine. Treatment should be stopped promptly if any mental or neurological signs develop. Convulsions are said to occur in about 50% of patients when the plasma concentration exceeds 20–25 mg/L, but the relationship to dose is not particularly close. No permanent damage appears to be caused. Cycloserine inhibits mammalian transaminases and this and the convulsant effects of the drug have been attributed to a metabolite, amino-oxyalanine. Use of the drug should be avoided in patients with previous fits or other neurological or psychiatric abnormalities. Rare side effects include rashes, cardiac arrhythmia and deficiency in folate and vitamin B12 leading to peripheral neuritis.
    It is occasionally used in MDR tuberculosis (with other antituberculosis drugs) and other mycobacterioses (with appropriate additional drugs).
  • Biologische Aktivität Excitatory amino acid. Partial agonist at the glycine modulatory site of the NMDA receptor.
  • Pharmakologie Cycloserine is readily absorbed orally and distributes throughout body fluids including the cerebrospinal fluid. The concentrations of cycloserine in tissues, body fluids, and the cerebrospinal fluid are approximately equal to the plasma level. Cycloserine is partially metabolized, and 60 to 80% is excreted unchanged by the kidney.
  • Clinical Use Neurological symptoms, which tend to appear in the first week of therapy, consist of dizziness, confusion, irritability, psychotic behavioral changes, and even suicidal ideation. Cycloserine is contraindicated in patients with underlying psychiatric and seizure disorders.Other side effects include occasional peripheral neuropathy and low magnesium levels.
  • Clinical Use D-(+)-4-Amino-3-isoxazolidinone (Seromycin) is an antibioticthat has been isolated from the fermentation beer of threedifferent Streptomyces species: S. orchidaceus, S. garyphalus,and S. lavendulus. It occurs as a white to pale yellow crystallinematerial that is very soluble in water. It is stable in alkaline,but unstable in acidic, solutions. The compoundslowly dimerizes to 2,5-bis(aminoxymethyl)-3,6-diketopiperazinein solution or standing.
    The structure of cycloserine was reported simultaneouslyby Kuehl et al. and Hidy et al.81 to be D-( +)-4-amino-3-isoxazolidinone. It has been synthesized byStammer et al. and by Smart et al.83 Cycloserine is stereochemicallyrelated to D-serine. However, the L-form hassimilar antibiotic activity.
    Although cycloserine exhibits antibiotic activity invitro against a wide spectrum of both Gram-negative andGram-positive organisms, its relatively weak potency andfrequent toxic reactions limit its use to the treatment of tuberculosis.It is recommended for patients who fail to respondto other tuberculostatic drugs or who are known tobe infected with organisms resistant to other agents. It isusually administered orally in combination with otherdrugs, commonly isoniazid.
  • läuterung methode Purify cycloserine by recrystallisation from aqueous EtOH or MeOH or aqueous NH3/EtOH or isoPrOH. Also recrystallise it from aqueous ammoniacal solution at pH 10.5 (100mg/mL) by diluting with 5 volumes of isopropanol and then adjusting to pH 6 with acetic acid. An aqueous solution, buffered to pH 10 with Na2CO3, can be stored in a refrigerator for 1week without decomposition. UV: max at 226nm (A1cm 1% 4.02). The tartrate salt has m 165-166o (dec), 166-168o (dec), and [] D 24 -41o (c 0.7, H2O). [Stammer et al. J Am Chem Soc 79 3236 1959, UV: Kuehl J Am Chem Soc 77 2344 1955, Beilstein 27 III/IV 5549.]
D-Cycloserine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Cycloserin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
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68-41-7, D-Cycloserine Verwandte Suche:
  • (+)-4-Amino-3-oxazolidinone
  • (r)-3-isoxazolidinon
  • 106-7
  • 3-Isoxazolidine, 4-amino-, (R)-
  • 3-Isoxazolidinone, 4-amino-, (+)-
  • 3-Isoxazolidinone, 4-amino-, (R)-
  • 3-Isoxazolidinone, 4-amino-, d-
  • 4-amino-,D-3-Isoxazolidinone
  • 4-Amino-3-isoxazolidinone
  • 4-Isoxazolidinamine, 3-oxo-
  • alpha-Cycloserine
  • Cicloserina
  • Closina
  • Cyclo-D-serine
  • Cyclomycin
  • Cyclorin
  • Cycloserin
  • Cycloserine, D-
  • D-CYCLOSERINE GAMMA-IRRADIATEDMOLECULAR BIOLOGY RE
  • D-Cycloserine,98%
  • Cycloserline
  • 3-Isoxazolidinone, 4-amino-, (4R)-
  • 3-Isoxazolidinone, 4-amino-, (+)- (8CI)
  • Closerin
  • NSC 154851
  • NSC 76029
  • 3-Isoxazolidinone,4-amino-,(4R)-(9CI)
  • D-Cycloserine, synthetic
  • (R)-(+)-Cycloserine, 98+%
  • (R)-4-Amino-3-isoxazolidone, 4-Amino-3-isoxazolidinone
  • (4R)-4-Amino-1,2-oxazolidin-3-one
  • Ceromycin
  • D-4-Amino-3-isoxazolone
  • Orientmycin
  • D-Cycloserin
  • (r)-3-isoxazolidinon(R)-4-Amino-3-isoxazolidone
  • Cycloserine (250 mg)
  • Cyloserine
  • D-Cycoloserine
  • (4R)-4-AMino-3-isoxazolidinone
  • (R)-(+)-4-Amino-3-isoxazolidinone Orientomycin Oxamycin
  • (R)-4-AMinoisoxazalidin-3-one
  • D-Cycloserine in stock GMP Factory
  • d-3-isoxazolidinon
  • D-4-Amino-3-isossazolidone
  • D-4-Amino-3-isoxazolidone
  • D-Oxamicina
  • D-Oxamycin
  • E-733-A
  • Farmiserina
  • Farmiserine
  • I-1431
  • Micoserina
  • Miroserina
  • Miroseryn
  • NJ-21
  • Novoserin
  • Oxamicina