Aclarubicin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Aclarubicin
Accession Number
DB11617
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • Aclacinomycin A
  • aclarubicina
External IDs
NSC-208734
Product Ingredients
IngredientUNIICASInChI Key
Aclarubicin hydrochloride501948RI6675443-99-1KUSMIBXCRZTVML-PCCPLWKKSA-N
Categories
UNII
74KXF8I502
CAS number
57576-44-0
Weight
Average: 811.878
Monoisotopic: 811.341520011
Chemical Formula
C42H53NO15
InChI Key
USZYSDMBJDPRIF-SVEJIMAYSA-N
InChI
InChI=1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3/t18-,19-,20-,24-,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1
IUPAC Name
methyl (1R,2R,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
SMILES
CC[C@@]1(O)C[C@H](O[C@H]2C[C@@H]([C@H](O[C@H]3C[C@H](O)[C@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@H](C)O3)[C@H](C)O2)N(C)C)C2=C(O)C3=C(C=C2[C@H]1C(=O)OC)C(=O)C1=C(C(O)=CC=C1)C3=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Jensen PB, Jensen PS, Demant EJ, Friche E, Sorensen BS, Sehested M, Wassermann K, Vindelov L, Westergaard O, Hansen HH: Antagonistic effect of aclarubicin on daunorubicin-induced cytotoxicity in human small cell lung cancer cells: relationship to DNA integrity and topoisomerase II. Cancer Res. 1991 Oct 1;51(19):5093-9. [PubMed:1655244]
  2. Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, Nieuwland M, Ovaa H, Rottenberg S, van Tellingen O, Janssen J, Huijgens P, Zwart W, Neefjes J: Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin. Nat Commun. 2013;4:1908. doi: 10.1038/ncomms2921. [PubMed:23715267]
  3. Pang B, de Jong J, Qiao X, Wessels LF, Neefjes J: Chemical profiling of the genome with anti-cancer drugs defines target specificities. Nat Chem Biol. 2015 Jul;11(7):472-80. doi: 10.1038/nchembio.1811. Epub 2015 May 11. [PubMed:25961671]
External Links
KEGG Drug
D02756
KEGG Compound
C18638
PubChem Compound
451415
PubChem Substance
347828010
ChemSpider
397638
BindingDB
50368351
ChEBI
74619
ChEMBL
CHEMBL502620
Wikipedia
Aclarubicin
ATC Codes
L01DB04 — Aclarubicin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentCerebroretinal Vasculopathy, Hereditary / Vasculopathy, Retinal, With Cerebral Leukodystrophy1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Relapsed Leukemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.218 mg/mLALOGPS
logP2.79ALOGPS
logP3.98ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.47ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area217.05 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity203.87 m3·mol-1ChemAxon
Polarizability84.31 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Anthracyclines
Sub Class
Not Available
Direct Parent
Anthracyclines
Alternative Parents
Tetracenequinones / Aminoglycosides / Anthracenecarboxylic acids / Anthraquinones / Naphthalenecarboxylic acids and derivatives / Disaccharides / O-glycosyl compounds / Tetralins / Aryl ketones / 1-hydroxy-2-unsubstituted benzenoids
show 16 more
Substituents
Anthracyclinone-skeleton / Anthracycline / Tetracenequinone / Aminoglycoside core / Anthracene carboxylic acid or derivatives / Anthracene carboxylic acid / 9,10-anthraquinone / 1,4-anthraquinone / Anthracene / 1-naphthalenecarboxylic acid or derivatives
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenols, trisaccharide derivative, methyl ester, polyketide, aminoglycoside, anthracycline, tetracenequinones (CHEBI:74619)

Drug created on August 25, 2016 17:13 / Updated on November 02, 2018 09:00