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1-β-D-Arabinofuranosylcytosinhydrochlorid

Cytarabine Hydrochloride

HCID 6252
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
69-74-9
Standard-SMILES
Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
InChIKey
KCURWTAZOZXKSJ-JBMRGDGGSA-N
Summenformel
C9H13N3O5.ClH
Durchschnittliche Molmasse
279,68 g/mol
Monoisotopische Masse
279,06219823

Überblick

Crystals (from aqueous ethanol) or fluffy white powder. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Cytarabine Hydrochloride
IUPAC
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
Lokaler Name
1-β-D-Arabinofuranosylcytosinhydrochlorid
Englischer Name
1-beta-D-Arabinofuranosylcytosine hydrochloride
Summenformel
C9H14ClN3O5
Molmasse
279.68

Namen und Synonyme

CYTARABINE HYDROCHLORIDE69-74-9Cytosine arabinoside hydrochlorideCytarabine HCl1-beta-D-Arabinofuranosylcytosine hydrochlorideCytosar hydrochlorideSpongocytidine hydrochlorideArabitin hydrochlorideAracytidine hydrochlorideU-19920AIretinDTXSID5024891
Weitere Namen anzeigen
ARA-Cac1075ALEXANCylocideAra-c.HaCytarbineARA-C HCL
Aracytin hydrochlorideNSC-6387833K3DB65911-beta-D-Arabinofuranosylcytosine monohydrochlorideArabinosylcytosine hydrochlorideDTXCID104891Arabinofuranosylcytosine hydrochloride2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-, monohydrochloride

Datenbank-Bezeichner

CAS
69-74-9
PubChem CID
6252
DTXSID
DTXSID5024891

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
129 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
2
Schwere Atome
18
Formalladung
0
Komplexität
383

Experimentelle und physikochemische Eigenschaften

Solubility · 2 Einträge

greater than or equal to 100 mg/mL at 63 °F (NTP, 1992)

>42 [ug/mL] (The mean of the results at pH 7.4)

Human DrugsBreast Feeding; Lactation; Milk, Human; Antimetabolites, Antineoplastic; Immunosuppressive Agents; Nucleosides
Melting Point356 to 360 °F (NTP, 1992)
Physical DescriptionCrystals (from aqueous ethanol) or fluffy white powder. (NTP, 1992)

Physikochemische Eigenschaften

Schmelzpunkt
197 · 197-198 °C(lit.)
storage temp.
2 · 2-8°C
Löslichkeit
14.2 mg/mL · insoluble in EtOH; ≥14.2 mg/mL in DMSO; ≥64.2 mg/mL in H2O
Aggregatzustand
crystalline
Farbe
White to off-white
Biologische Quelle
synthetic (inorganic)
Stabilität
Stable. Combustible. Incompatible with strong oxidizing agents.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P318, P321, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 12-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21560
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound include leukopenia, thrombocytopenia, anemia, megaloblastosis, hepatic dysfunction, thromobophlebitis at the site of injection, and conjunctivitis. Other symptoms include potent bone marrow suppression, reduced reticulocytes, anorexia, nausea, vomiting, diarrhea, oral and anal inflammation or ulceration, fever, rash, bleeding (all sites), sepsis, pneumonia, cellulitis at injection site, skin ulceration, urinary retention, renal dysfunction, neuritis, neural toxicity, sore throat, esophageal ulceration, esophagitis, chest pain, bowel necrosis, abdominal pain, freckling, jaundice, dizziness, alopecia, allergic edema, anaphylaxis, pruritus, shortness of breath, urticaria and headache. "Flu-like" syndrome may occur. Joint pains may also occur. Eye irritation has been reported. Other eye effects include reversible glittering opacities, pain, punctuate epithelial keratitis and photophobia.

Reactive GroupAlcohols and Polyols

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification · 3 Einträge

Antimetabolites that are useful in cancer chemotherapy.

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Verwendung und Herstellung

UsesFor the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia.

Anwendungen

VerwendenAntiviral.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

ElectrophoresisEthanolLanthantrihydroxidCytarabinCytidinNatriumhydroxid

Zugehörige Reaktionen

4
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 858365
HRID 858365als Produktuspto-grants-2006_12
Reaktionsgleichung von HRID 859116
HRID 859116als Produktuspto-grants-2006_12
Reaktionsgleichung von HRID 1781981
HRID 1781981als Produktuspto-grants-2009_03
Reaktionsgleichung von HRID 1987727
HRID 1987727als Produktuspto-grants-2009_06

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL1256472
UNII
33K3DB6591
EC Number
200-713-9
InChI
InChI=1/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/s3
InChIKey
KCURWTAZOZXKSJ-XKIMMOKZSA-N
SMILES
N1([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=CC(N)=NC1=O.[H]Cl |&1:1,3,6,8,r|
CAS Datenbank
69 · 69-74-9(CAS DataBase Reference)
EPA chemische Informationen
Cytarabine hydrochloride (69-74-9)
Reactivity Profile
CYTARABINE HYDROCHLORIDE undergoes decomposition in acidic solutions.
Air and Water ReactionsWater soluble. Hydrolysis occurs readily, especially with acid.
Hazard Classes and CategoriesSkin Sens. 1 (100%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material may be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxikologische Informationen

Exposure RoutesLess than 20% of the orally administered dose is absorbed from the gastrointestinal tract.
Toxicity Summary · 1 Eintrag

Cytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase) and under certain conditions blocking the progression of cells from the G1 phase to the S-phase. Although the mechanism of action is not completely understood, it appears that cytarabine acts through the inhibition of DNA polymerase. A limited, but significant, incorporation of cytarabine into both DNA and RNA has also been reported.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataCytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise.

Sicherheitsdaten

wgk
3
hs_code
29389090
RTECS-Nr.
HA5500000
risk_code
36-43-63
Toxizität
LD50 oral in rat: > 3200mg/kg
hazard_code
Xn
safety_code
26-36/37
hazard_class
IRRITANT
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Eye Irrit. 2Muta. 2Repr. 2Skin Sens. 1
Ancitabine
Ammoniak, wasserfrei
Methanol
Hydrogenchlorid

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