CAS 25316-40-9 Doxorubicin Hydrochloride (HCID 443939)

概要

Doxorubicin Hydrochloride (Adriamycin) can cause cancer according to an independent committee of scientific and health experts. It can cause developmental toxicity and male reproductive toxicity according to state or federal government labeling requirements.

名称と識別子

優先名称: Doxorubicin Hydrochloride
IUPAC: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
現地名: ドキソルビシン·塩酸塩
英語名: Doxorubicin hydrochloride
分子式: C27H29NO11.ClH
分子量: 579.98

名称と別名

Doxorubicin Hydrochloride25316-40-9Doxorubicin HClADRIAMYCIN HYDROCHLORIDEAdriacinAdriamycin PFSAdriamycin RDFADRIAMYCIN, HYDROCHLORIDEAdriablastina csDTXSID3030636doxorubicin.HClDoxorubicini hydrochloridum

名称をさらに表示

リポドックスアドリブラスチナRDアドリアシンドキソルビシン塩酸塩アドリブラスチン塩酸塩ADM塩酸塩アドリアブラスチナCS(8S)-10α-[(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシル)オキシ]-7,8,9,10-テトラヒドロ-6,8α,11-トリヒドロキシ-8-(ヒドロキシアセチル)-1-メトキシ-5,12-ナフタセンジオン·塩酸塩(8S)-1-メトキシ-6,8α,11-トリヒドロキシ-8-(ヒドロキシアセチル)-10α-[(3-アミノ-2,3,6-トリデオキシ-α-L-lyxo-ヘキソピラノシル)オキシ]-7,8,9,10-テトラヒドロ-5,12-ナフタセンジオン·塩酸塩ADM【アドリアマイシン】塩酸アドリブラスチンアドリブラスチンヒドロキシダウノルビシン塩酸塩アドリブラスチナ塩酸ドキソルビシンドキソルビシン·塩酸塩アドリアブラスチナアドリアマイシンドキソルビシン, 塩酸塩, >>95%ドキソルビシン塩酸塩DOXADRDoxorubicin HCIDOX HClCAELYXDOX HYDROCHLORIDEDoxorubicin hydrochlorid(8s-cis)-10-[(3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride

hydroxydaunomycin hydrochloride82F2G7BL4EDoxorubicin citric acid saltDTXCID1010636Liposomal doxorubicin hydrochlorideDOXORUBICIN HYDROCHLORIDE LIPOSOME5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-FI 106

データベース識別子

CAS: 25316-40-9
PubChem CID: 443939
DTXSID: DTXSID3030636
ChEMBL: CHEMBL359744
ChEBI: CHEBI:31522
UNII: 82F2G7BL4E
EC Number: 246-818-3

物性

構造計算による物性

極性表面積: 206 Å²
水素結合供与体数: 7
水素結合受容体数: 12
回転可能結合数: 5
重原子数: 40
形式電荷: 0
複雑度: 977

実験および物理化学的性質

SolubilitySoluble (NTP, 1992)

Human Drugs · 6 件

Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Anthracyclines; Antibiotics, Antineoplastic; Topoisomerase II Inhibitors

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Melting Point399 to 401 °F (Decomposes) (NTP, 1992)

Physical DescriptionAdriamycin hydrochloride appears as orange-red thin needles. Aqueous solutions yellow-orange at acid pHs, orange-red at neutral pHs, and violet blue over pH 9. (NTP, 1992)

物理化学的性質

融点: 216 °C · 216 °C (dec.)(lit.)
比旋光度: 20 · D20 +248±2° (c = 0.1 in methanol)
貯蔵温度: 2 · 2-8°C
溶解性: 100 mg/ml · DMSO に 100mg/ml で可溶、エタノールに極めて不溶、弱火で水に可溶、濃度 10mg/ml。
酸解離定数(Pka): 8.25 · pKa 8.25±0.60 (Uncertain);8.43±0.70 (Uncertain);11.9±0.4 (Uncertain);12.95±0.1 (Uncertain);13.8±0.70 (Uncertain)
外見: 個体
色: オレンジからダークレッド
由来生物: synthetic (organic)
水溶解度: 水に溶ける。
Merck: 14 · 14,3439
BRN: 4229251 · 4229251
安定性: -20 °C · その水溶液は、-20°C で最大 3 か月間保存できます。
InChIKey: MWWSFMDVAYGXBV-RUELKSSGSA-N
SMILES: Cl[H].COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO
CAS データベース: 25316 · 25316-40-9(CAS DataBase Reference)
EPAの化学物質情報: Doxorubicin hydrochloride (25316-40-9)

化学的性質 · 1 件

化学的特性Doxorubicin is an orange to red cake-like or needle-like crystalline solid. It is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var. caesius. Doxorubicin hydrochloride is an orange-red, crystalline, hygroscopic powder that is soluble in water and slightly soluble in methanol.

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H302 (77.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 158 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Hazard Traits - Carcinogenicity; Developmental Toxicity; Reproductive Toxicity

Adriamycin hydrochloride: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsThis compound is probably combustible. (NTP, 1992)

Reactive GroupAmines, Phosphines, and Pyridines

Reactivity Profile · 1 件

Amines, like adriamycin hydrochloride, are weak chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. 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.

Air and Water ReactionsWater soluble.

Hazard Classes and CategoriesAcute Tox. 4 (77.8%)

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical carbon dioxide, foam 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.

Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

毒性情報

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Doxorubicin hydrochloride

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

F: 10-21
wgk: 3
rtecs: QI9295900
ridadr: UN2811
毒性: LD50 i.v. in mice: 21.1 mg/kg (Bertazzoli, 1970)
hs_code: 29419090
risk_code: 45-22-40-26/27/28-36/38
hazard_code: T,T+,Xi
safety_code: 53-45-36/37/39-22-7/9
hazard_class: 6.1
Hazard Classifications: Acute Tox. 4 OralCarc. 1BMuta. 1BRepr. 1B
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

FDA Pharmacological Classification · 4 件

DOXORUBICIN HYDROCHLORIDE

Anthracycline Topoisomerase Inhibitor [EPC]; Anthracyclines [CS]; Topoisomerase Inhibitors [MoA]

DOXORUBICIN HYDROCHLORIDE LIPOSOME

Topoisomerase Inhibitors [MoA]; Anthracyclines [CS]; Anthracycline Topoisomerase Inhibitor [EPC]

MeSH Pharmacological Classification · 2 件

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.

応用分野 · 5 件

用途ドキソルビシン（doxorubicin）は、抗悪性腫瘍剤（抗がん剤）の一種。

用途薬理研究用。

用途アントラサイクリン系抗生物質です。トポイソメラーゼⅡを阻害することにより DNA 障害作用を示します。

使用Doxorubicin hydrochloride (adriamycin hydrochloride) is an antitumour agent that has been formulated as a salt to achieve higher water solubility. While the salt shares the same pharmacological properties as doxorubicin free base, its greater water solubility may offer advantages in some in vitro applications. Physicochemical properties and chromatographic behaviour will depend on whether the pH is buffered. In non-pH controlled systems the free base and salt may behave differently.

一般的な説明Adriamycin hydrochloride appears as orange-red thin needles. Aqueous solutions yellow-orange at acid pHs, orange-red at neutral pHs, and violet blue over pH 9. Doxorubicin is available as both the conventional dosageform and a liposomal preparation, both of which are administeredby infusion. Doxorubicin HCl powder is available in10-, 20-, 50-, and 150-mg vials and is widely used in treatingvarious cancers, including leukemias, soft and bone tissuesarcomas, Wilms tumor, neuroblastoma, small cell lungcancer, and ovarian and testicular cancer.