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Daunorubicin Hydrochloride

HCID 62770
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GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
11016-72-1
Standard-SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
InChIKey
GUGHGUXZJWAIAS-QQYBVWGSSA-N
Summenformel
C27H30ClNO10
Durchschnittliche Molmasse
564 g/mol
Monoisotopische Masse
563,1558238

Namen und Bezeichner

Bevorzugter Name
Daunorubicin Hydrochloride
IUPAC
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride

Namen und Synonyme

DAUNORUBICIN HYDROCHLORIDE23541-50-6DAUNORUBICIN HCLDaunomycin hydrochlorideDaunoblastinaRP 13057 hydrochlorideRubidomycin hydrochlorideOndenaDaunomycin chlorohydrateDaunomycin, hydrochlorideRP-13057 HydrochlorideDaunoblastin
Weitere Namen anzeigen
NDC 0082-4155DTXSID0033382Daunorubicin (as hydrochloride)UD984I04LZFI 6339 HYDROCHLORIDEFI-6339 HYDROCHLORIDENSC-82151DTXCID8013382

Datenbank-Bezeichner

CAS
11016-72-1、23541-50-6
PubChem CID
62770
DTXSID
DTXSID0033382
ChEMBL
CHEMBL1563
ChEBI
CHEBI:31456
UNII
UD984I04LZ
EC Number
245-723-4

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

Polarare Oberfläche (TPSA)
186 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
11
Frei drehbare Bindungen
4
Schwere Atome
39
Formalladung
0
Komplexität
960

Experimentelle und physikochemische Eigenschaften

SolubilitySoluble (NTP, 1992)
Melting Point370 to 374 °F (decomposes) (NTP, 1992)
Physical DescriptionDaunorubicin hydrochloride appears as orange-red powder. Thin red needles decomposing at 188-190 °C. An anti-cancer drug.

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 · 5 Einträge

Danger

H301 (70.2%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (29.8%): Harmful if swallowed [Warning Acute toxicity, oral];H334 (66.3%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H341 (32.7%): Suspected of causing genetic defects [Warning Germ cell mutagenicity];H351 (99%): Suspected of causing cancer [Warning Carcinogenicity];H360 (32.7%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P233, P260, P264, P270, P271, P280, P284, P301+P316, P301+P317, P304+P340, P318, P321, P330, P342+P316, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 104 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Hazard Traits - Developmental Toxicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product

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

Other Safety Information · 1 Eintrag

IMAP assessments - 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, hydrochloride, (8S-cis)-: Human health tier I assessment;IMAP assessments - 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, hydrochloride, (8S-cis)-: Environment tier I assessment

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesHepatic Route of Elimination: Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion. Half Life: 18.5 hours
FDA Pharmacological Classification · 2 Einträge

DAUNORUBICIN HYDROCHLORIDE

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

MeSH Pharmacological Classification · 2 Einträge

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.

Verwendung und Herstellung

UsesFor remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.

Zugehörige Reaktionen

10
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 620906
HRID 620906als Eduktuspto-grants-1989_04
Reaktionsgleichung von HRID 894509
HRID 894509als Eduktuspto-grants-1981_08
Reaktionsgleichung von HRID 1076472
HRID 1076472als Eduktuspto-grants-1976_05
Reaktionsgleichung von HRID 1085235
HRID 1085235als Eduktuspto-grants-1991_04
Reaktionsgleichung von HRID 1249492
HRID 1249492als Eduktuspto-grants-1986_12
Reaktionsgleichung von HRID 1658482
HRID 1658482als Eduktuspto-grants-1976_06
Reaktionsgleichung von HRID 1703941
HRID 1703941als Eduktuspto-grants-1978_11
Reaktionsgleichung von HRID 1703942
HRID 1703942als Eduktuspto-grants-1978_11
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DOT LabelPoison
Fire Hazards · 1 Eintrag

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion or sodium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2024)

Health Hazards · 1 Eintrag

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination. (ERG, 2024)

Reactive GroupAlcohols and Polyols;Ethers;Ketones;Phenols and Cresols;Salts, Acidic;Acetals, Ketals, Hemiacetals, and Hemiketals
Reactivity ProfileDAUNORUBICIN HYDROCHLORIDE may emit toxic oxides of nitrogen when heated.
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 3 (70.2%);Acute Tox. 4 (29.8%);Resp. Sens. 1 (66.3%);Muta. 2 (32.7%);Carc. 2 (99%);Repr. 1B (32.7%)

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;SMALL FIRE: Dry chemical, CO2 or water spray.;LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Nonfire Spill Response · 1 Eintrag

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

Isolation and Evacuation · 1 Eintrag

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

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 a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxikologische Informationen

TreatmentInfuse 10 to 20 mL/kg isotonic fluid. If hypotension persists, administer dopamine. (A704)
Health EffectsAntibiotic resistance. Toxic manifestations of Daunorubicin include bone marrow depression, stomatitis, alopecia, gastrointestinal disturbances, and dermatological manifestations. Cardiac toxicity is a pecular effect. (A723)
Exposure RoutesIntravenous
Toxicity Summary · 1 Eintrag

Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.

Signs and Symptomssymptoms include gastrointestinal disturbances. (A723)
Carcinogen Classification2B, possibly carcinogenic to humans. (L135)
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Daunorubicin hydrochloride

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation · 1 Eintrag

◉ Summary of Use during Lactation;Most sources consider breastfeeding to be contraindicated during maternal antineoplastic drug therapy, especially anthracyclines such as daunorubicin. It might be possible to breastfeed safely during intermittent therapy with an appropriate period of breastfeeding abstinence. Based on the 27-hour half-life of the active metabolite daunorubicinol a minimum of 6 days would be required before resuming nursing.;Chemotherapy may adversely affect the normal microbiome and chemical makeup of breastmilk. Women who receive chemotherapy during pregnancy are more likely to have difficulty nursing their infant.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.

Toxicity DataLD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV)

Regulatorische Informationen

Regulatory Information · 2 Einträge

Hazard Traits - Developmental Toxicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product

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