NAV

Aclarubicin

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

Identification

Generic Name
Aclarubicin
DrugBank Accession Number
DB11617
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 811.878
Monoisotopic: 811.341520011
Chemical Formula
C42H53NO15
Synonyms
  • Aclacinomycin A
  • Aclarubicin
  • aclarubicina
External IDs
  • NSC-208734
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Aclarubicin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Aclarubicin is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Aclarubicin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Aclarubicin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Aclarubicin is combined with Bupivacaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Aclarubicin hydrochloride501948RI6675443-99-1KUSMIBXCRZTVML-PCCPLWKKSA-N

Categories

ATC Codes
L01DB04 — Aclarubicin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,4-anthraquinone / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 1-naphthalenecarboxylic acid or derivatives / 9,10-anthraquinone / Acetal / Alcohol / Amine / Amino acid or derivatives / Amino saccharide
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenols, trisaccharide derivative, methyl ester, polyketide, aminoglycoside, anthracycline, tetracenequinones (CHEBI:74619)
Affected organisms
Not Available

Chemical Identifiers

UNII
74KXF8I502
CAS number
57576-44-0
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

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. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D02756
KEGG Compound
C18638
PubChem Compound
451415
PubChem Substance
347828010
ChemSpider
397638
BindingDB
50368351
RxNav
239
ChEBI
74619
ChEMBL
CHEMBL502620
ZINC
ZINC000085537142
Wikipedia
Aclarubicin

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentAcute Myeloid Leukemia3
3Unknown StatusTreatmentAcute Myeloid Leukemia / Induction chemotherapy1
2Not Yet RecruitingTreatmentAcute Myeloid Leukemia / Elderly Patients / Newly Diagnosed1
2Unknown StatusTreatmentAcute Myeloid Leukemia1
2Unknown StatusTreatmentAcute Myeloid Leukemia / 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/MSsplash10-03di-0311522590-20765daa53a2656270d9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0209534030-39857229569dc25710c9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-1634029140-41b8397b0506b1a4b9a4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0509102110-96d22bdf22b6a9992aef
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0733231790-5f2f1e5b0eee43e2c3a5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-0707546490-33aa0a3b3f48c87e8263
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-310.8786964
predicted
DarkChem Lite v0.1.0
[M-H]-263.93405
predicted
DeepCCS 1.0 (2019)
[M+H]+308.9171964
predicted
DarkChem Lite v0.1.0
[M+H]+265.65778
predicted
DeepCCS 1.0 (2019)
[M+Na]+310.4936964
predicted
DarkChem Lite v0.1.0
[M+Na]+271.86954
predicted
DeepCCS 1.0 (2019)

Drug created at August 25, 2016 23:13 / Updated at February 21, 2021 18:53