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Vidarabin

Vidarabine Struktur
5536-17-4
CAS-Nr.
5536-17-4
Bezeichnung:
Vidarabin
Englisch Name:
Vidarabine
Synonyma:
(2R,3S,4S,5R)-2-(6-AMino-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;ARABINOFURANOSYL-ADENINE;9-β-D-Arabinofuranosyladenine;ci673;CI763;vira-a;ci-673;Ara-Ar;Ara-rA;b-Ara-A
CBNumber:
CB4697866
Summenformel:
C10H13N5O4
Molgewicht:
267.25
MOL-Datei:
5536-17-4.mol

Vidarabin Eigenschaften

Schmelzpunkt:
260-265 °C (dec.)
alpha 
D27 -5° (c = 0.25)
Siedepunkt:
410.43°C (rough estimate)
Dichte
1.3382 (rough estimate)
Brechungsindex
1.7610 (estimate)
storage temp. 
-20°C
L?slichkeit
DMSO (Slightly, Heated)
Aggregatzustand
Powder
pka
pKa 3.55(H2O t=20 I=0.1 (KCl)) (Uncertain);11.4 (Uncertain)
Farbe
White to Off-white
Wasserl?slichkeit
Soluble in DMF (10 mg/ml), 0.5 M HCl (50 mg/ml), DMSO (53 mg/ml at 25°C), ethanol (<1 mg/ml at 25°C), and water (3 mg/ml at 25°C).
Merck 
13,10039
BRN 
624881
InChIKey
OIRDTQYFTABQOQ-UHTZMRCNSA-N
LogP
-0.755 (est)
CAS Datenbank
5536-17-4(CAS DataBase Reference)
EPA chemische Informationen
Vidarabine (5536-17-4)

Sicherheit

Kennzeichnung gef?hrlicher Xn,Xi
R-S?tze: 63-36/37/38
S-S?tze: 36/37-36-26
RIDADR  2811
WGK Germany  3
RTECS-Nr. AU6200000
10-23
TSCA  Yes
HazardClass  6.1(a)
PackingGroup  II
HS Code  29349990
Giftige Stoffe Daten 5536-17-4(Hazardous Substances Data)
Toxizit?t LD50 in mice (mg/kg): 4677 i.p.; >7950 orally (Kurtz)

Vidarabin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R63:Kann das Kind im Mutterleib m?glicherweise sch?digen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Beschreibung

Vidarabine (adenine arabinoside) is the stereoisomer of adenosine. This analog of a purine nucleoside exhibits selective activity against the herpes virus. The ribose residue is replaced with an arabinose residue. Like acyclovir, it turns into mono-, di-, and triphosphate in cells infected by a virus, thus inhibiting DNA polymerase, and correspondingly preventing DNA synthesis of the virus approximately 20–40 times more than in “host” cells. It is easily metabolized to a less active, yet nonetheless antiviral compound—arabinosylhypoxanthine. It has been successfully used for herpetic encephalitis, and for complicated shingles. It is used in the form of eye drops for herpetic keratoconjuctivitis. A synonym of this drug is Vira-A.

Chemische Eigenschaften

Crystalline

Verwenden

Vidarabine, is an antiviral drug which is active against herpes simplex and varicella zoster viruses.

Indications

Vidarabine (adenine arabinoside, Vira-A) is an adenine nucleoside analogue containing arabinose in place of ribose. It is obtained from cultures of Streptomyces antibioticus and has activity against HSV-1, HSV-2, VZV, CMV, HBV, poxviruses, hepadnaviruses, rhabdoviruses, and certain RNA tumor viruses.

Allgemeine Beschreibung

Chemically, vidarabine (Vira-A), is 9--D-arabinofuranosyladenine.The drug is the 2'epimer of natural adenosine.Introduced in 1960 as a candidate anticancer agent, vidarabinewas found to have broad-spectrum activity against DNAviruses.The drug is active against herpesviruses,poxviruses, rhabdoviruses, hepadnavirus, and some RNAtumor viruses. Vidarabine was marketed in the United Statesin 1977 as an alternative to idoxuridine for the treatment ofHSV keratitis and HSV encephalitis. Although the agent wasinitially prepared chemically, it is now obtained by fermentationwith strains of Streptomyces antibioticus.
The antiviral action of vidarabine is completely confinedto DNA viruses. Vidarabine inhibits viral DNA synthesis.Enzymes within the cell phosphorylate vidarabine to thetriphosphate, which competes with deoxyadenosine triphosphatefor viral DNA polymerase. Vidarabine triphosphate isalso incorporated into cellular and viral DNA, where it actsas a chain terminator. The triphosphate form of vidarabinealso inhibits a set of enzymes that are involved in methylationof uridine to thymidine: ribonucleoside reductase, RNApolyadenylase, and S-adenosylhomocysteine hydrolase.
At one time in the United States, intravenous vidarabinewas approved for use against HSV encephalitis, neonatalherpes, and herpes or varicella zoster in immunocompromisedpatients. Acyclovir has supplanted vidarabine as thedrug of choice in these cases.

Air & Water Reaktionen

Insoluble in water.

Reaktivit?t anzeigen

Vidarabine is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Brandgefahr

Flash point data for Vidarabine are not available; however Vidarabine is probably combustible.

Mechanism of action

Vidarabine’s specific mechanism of action is not fully understood. Cellular enzymes convert this drug to a triphosphate that inhibits DNA polymerase activity. Vidarabine triphosphate competes with deoxyadenosine triphosphate (dATP) for access to DNA polymerase and also acts as a chain terminator. Although vidarabine is incorporated into host DNA to some extent, viral DNA polymerase is much more susceptible to inhibition by vidarabine. Vidarabine also inhibits ribonucleoside reductase and other enzymes. Resistance occurs as a result of DNA polymerase mutation.

Pharmakokinetik

Vidarabine is deaminated rapidly by adenosine deaminase, which is present in serum and red blood cells. The enzyme converts vidarabine to its principal metabolite, arabinosyl hypoxanthine (ara-HX), which has weak antiviral activity. The half-life of vidarabine is approximately 1 hour, whereas ara-HX has a half-life of 3.5 hours. The drug is detected mostly in the kidney, liver, and spleen, because 50% of it is recovered in the urine as ara-HX. Levels of vidarabine in CSF fluid are 50% of those in the plasma.

Clinical Use

The principal use of vidarabine is in the treatment of HSV keratoconjunctivitis. It is also used to treat superficial keratitis in patients unresponsive or hypersensitive to topical idoxuridine.

Nebenwirkungen

The most commonly observed side effects associated with vidarabine are lacrimation, burning, irritation, pain, and photophobia. Vidarabine has oncogenic and mutagenic potential; however, the risk of systemic effects is low because of its limited absorption. It should not be used in conjunction with ophthalmic corticosteroids, since these drugs increase the spread of HSV infection and may produce side effects such as increased intraocular pressure, glaucoma, and cataracts.

Sicherheitsprofil

Poison by ingestion and intravenous routes. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by intravenous route: central nervous system, blood, and other effects. A skin and eye irritant. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Vidarabin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Vidarabin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 387)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Shaanxi TNJONE Pharmaceutical Co., Ltd
+8618092446649
sarah@tnjone.com China 1143 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886
info@dakenam.com China 18751 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3009 60
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
Win-Win Chemical CO., Limited
0086-577-64498589
sales@win-winchemical.com CHINA 998 58
Jinan Carbotang Biotech Co.,Ltd.
+8615866703830
figo.gao@foxmail.com China 8497 58
Yunbio Tech Co.,Ltd.
+86-010-60605551 +86-18046518538
yunbiochem@126.com China 321 58
Xiamen AmoyChem Co., Ltd
+86-86-5926051114 +8618959220845
sales@amoychem.com China 6383 58
Nanjing Baifuli Technology Co., Ltd.
+86-15335185688
sales@unisyn.cn CHINA 332 58

5536-17-4(Vidarabin)Verwandte Suche:


  • ARABINOSYL-ADENINE
  • 6-AMINO-9-BETA-D-ARABINOFURANOSYLPURINE
  • ADENINE-BETA-D-ARABINOFURANOSIDE
  • ADENINE-9-BETA-D-ARABINOFURANOSIDE
  • 9-BETA-D-ARABINOSYLADENINE
  • 9-BETA-D-ARABINOFURANOSYLADENINE
  • 2'-ARAADENOSINE
  • ADENINE-9-BETA-D-ARABINOFURANOSIDE (VIDARABINE)
  • VIDARBINE
  • ADENINE 9-β-D-ARABINOFURANOSIDE (9-β-D-ARABINOFURANOSYLADENINE)
  • Adenine-9-â-D-arabinofuranoside
  • adenine-9-beta-arabinofuranoside
  • (2R,3S,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • SPONGOADENOSINE
  • VIDARABINE
  • 9-arabinosyladenine
  • 9-beta-d-arabinofuranosyl-9h-purin-6-amin
  • 9-beta-d-arabinofuranosyl-adenin
  • adeninearabinoside
  • vira-a
  • ADENINE 9-B-D-ARABINOFURANOSIDE
  • ADENINE 9-SS-D-ARABINOFURANOSIDE
  • 9-beta-D-Ribofuranosylsdenine
  • 9--D-Arabinosyladenine
  • ARABINOADENOSINE
  • 9-β-D-Arabinofuranosyl adenine
  • 9-β-D-Arabinofuranosyladenine monohydrate
  • VIDARABINE,USP
  • 9-SS-D-ARABINOFURANOSYL-ADENINE
  • 9-SS-D-ARABINOFURANOSYL-ADENINE(ARA-A)
  • 6-Amino-9-b-D-arabinofuranosylpurine
  • 9-b-D-Arabinoadenosine
  • 9-b-D-Arabinofuranosyl-9H-purin-6-amine
  • 9-b-D-Arabinofuranosyladenine
  • 9-b-D-Arabinosyladenine
  • 9H-Purin-6-amine, 9-b-D-arabinofuranosyl- (9CI)
  • Adenine b-D-arabinofuranoside
  • Adenine, 9-b-D-arabinofuranosyl- (7CI, 8CI)
  • b-Ara-A
  • b-D-Arabinofuranosyladenine
  • b-D-Arabinosyladenine
  • NSC 247519
  • NSC 404241
  • Vidarabine anhydrous
  • 9-beta-D-Ribofuranosyl sdenine (AR)
  • VIDARABINE[9-BETA-D-ARABINOSYLADENINE] (2R,3S,4S,5R)-2-(6-AMIN
  • 9-B-D-ARABINO FURANOSYL ADENINE HYDRATE
  • araadenosine
  • arasena-a
  • beta-ara-a
  • beta-d-arabinosyladenine
  • ci673
  • ci-673
  • vidarabin
  • 9-β-D-Arabinofuranosyladenine, Ara-A, Vidarabine
  • CI763
  • 9H-Purin-6-amine, 9-b-D-arabinofuranosyl-
  • 9-(β-D-Arabinoribofuranosyl) adenine
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