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塩酸シタラビン

Cytarabine Hydrochloride

HCID 6252
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
69-74-9
標準SMILES
Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
InChIKey
KCURWTAZOZXKSJ-JBMRGDGGSA-N
分子式
C9H13N3O5.ClH
平均分子量
279.68 g/mol
単同位体質量
279.06219823

概要

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

名称と識別子

優先名称
Cytarabine Hydrochloride
IUPAC
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
現地名
塩酸シタラビン
英語名
1-beta-D-Arabinofuranosylcytosine hydrochloride
分子式
C9H14ClN3O5
分子量
279.68

名称と別名

CYTARABINE HYDROCHLORIDE69-74-9Cytosine arabinoside hydrochlorideCytarabine HCl1-beta-D-Arabinofuranosylcytosine hydrochlorideCytosar hydrochlorideSpongocytidine hydrochlorideArabitin hydrochlorideAracytidine hydrochlorideU-19920AIretinDTXSID5024891
名称をさらに表示
アラシチジン塩酸塩シタラビン塩酸塩1-β-D-アラビノフラノシルシトシン·塩酸塩アラシチン塩酸塩スポンゴシチジン塩酸塩アラビノシルシトシン塩酸塩シトサル塩酸塩シトシンアラビノシド塩酸塩4-アミノ-1-β-D-アラビノフラノシルピリミジン-2(1H)-オン·塩酸塩シトシン Β-D-アラビノフラノシド 塩酸塩塩酸シタラビン4-アミノ-1-β-D-アラビノフラノシルピリミジン-2(1H)-オン・塩酸塩1-β-D-アラビノフラノシルシトシン・塩酸塩ARA-Cac1075ALEXANCylocideAra-c.HaCytarbineARA-C HCL
Aracytin hydrochlorideNSC-6387833K3DB65911-beta-D-Arabinofuranosylcytosine monohydrochlorideArabinosylcytosine hydrochlorideDTXCID104891Arabinofuranosylcytosine hydrochloride2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-, monohydrochloride

物性

構造計算による物性

極性表面積
129 Ų
水素結合供与体数
5
水素結合受容体数
5
回転可能結合数
2
重原子数
18
形式電荷
0
複雑度
383

実験および物理化学的性質

Solubility · 2 件

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)

物理化学的性質

融点
197 · 197-198 °C(lit.)
貯蔵温度
2 · 2-8°C
溶解性
14.2 mg/mL · insoluble in EtOH; ≥14.2 mg/mL in DMSO; ≥64.2 mg/mL in H2O
外見
結晶性
色
ホワイトからオフホワイト
由来生物
synthetic (inorganic)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
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|

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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 件

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
Reactivity ProfileCYTARABINE HYDROCHLORIDE undergoes decomposition in acidic solutions.

化学と産業

薬理情報

Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification · 3 件

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.

用途と製造

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

応用分野

使用Antiviral.

一般的な説明Crystals (from aqueous ethanol) or fluffy white powder.

上流・下流製品情報

上流原料

Electrophoresisエタノール水酸化ランタンシタラビンシチジン

関連反応

4 件
反応記録を作成
HRID 858365 の反応式
HRID 858365生成物としてuspto-grants-2006_12
HRID 859116 の反応式
HRID 859116生成物としてuspto-grants-2006_12
HRID 1781981 の反応式
HRID 1781981生成物としてuspto-grants-2009_03
HRID 1987727 の反応式
HRID 1987727生成物としてuspto-grants-2009_06

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
69-74-9
PubChem CID
6252
DTXSID
DTXSID5024891
ChEMBL
CHEMBL1256472
UNII
33K3DB6591
EC Number
200-713-9
CAS データベース
69 · 69-74-9(CAS DataBase Reference)
EPAの化学物質情報
Cytarabine hydrochloride (69-74-9)

化学的性質

化学的特性Crystalline

Air and Water ReactionsWater soluble. Hydrolysis occurs readily, especially with acid.
Hazard Classes and CategoriesSkin Sens. 1 (100%)

安全と保護具

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

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 件

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 件

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)

毒性情報

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

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.

安全データ

wgk
3
rtecs
HA5500000
毒性
LD50 oral in rat: > 3200mg/kg
hs_code
29389090
risk_code
36-43-63
hazard_code
Xn
safety_code
26-36/37
hazard_class
IRRITANT
Hazard Classifications
Eye Irrit. 2Muta. 2Repr. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
水酸化ナトリウム
(2R,3R,3aS,9aR)-2,3,3a,9a-テトラヒドロ-6-アミノ-3-ヒドロキシ-4aH-フロ[2',3':4,5]オキサゾロ[3,2-a]ピリミジン-2-メタノール
アンモニア
メタノール
塩酸

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