Pirarubicin

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

Identification

Name
Pirarubicin
Accession Number
DB11616
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • Adriamycin, tetrahydropyranyl
  • Theprubicin
  • THP-Adm
  • THP-Doxorubicin
Product Ingredients
IngredientUNIICASInChI Key
Pirarubicin hydrochlorideE7V83174BE95343-20-7ZPHYPKKFSHAVOE-YZIXBPQXSA-N
Categories
UNII
D58G680W0G
CAS number
72496-41-4
Weight
Average: 627.643
Monoisotopic: 627.231575635
Chemical Formula
C32H37NO12
InChI Key
KMSKQZKKOZQFFG-YXRRJAAWSA-N
InChI
InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
IUPAC Name
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yloxy]oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
SMILES
[H][C@]1(N)C[C@]([H])(O[C@@]2([H])C[C@@](O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=C(C=CC=C2OC)C4=O)C(=O)CO)O[C@@]([H])(C)[C@@]1([H])O[C@]1([H])CCCCO1

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
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Pirarubicin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Pirarubicin.Experimental
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Pirarubicin.Approved, Investigational, Withdrawn
Anthrax immune globulin humanThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Anthrax immune globulin human.Approved
Bacillus calmette-guerin substrain connaught live antigenThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Bacillus calmette-guerin substrain connaught live antigen.Approved, Investigational
Bacillus calmette-guerin substrain tice live antigenThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Bacillus calmette-guerin substrain tice live antigen.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Pirarubicin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Pirarubicin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Pirarubicin.Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Pirarubicin is combined with Clostridium tetani toxoid antigen (formaldehyde inactivated).Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Pirarubicin is combined with Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated).Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Pirarubicin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Pirarubicin.Experimental
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Pirarubicin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Pirarubicin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Pirarubicin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Pirarubicin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Pirarubicin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Pirarubicin.Approved, Investigational
FingolimodPirarubicin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Pirarubicin is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Pirarubicin is combined with GI-5005.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Pirarubicin.Experimental
Hepatitis A VaccineThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Hepatitis A Vaccine.Approved
Hepatitis B Vaccine (Recombinant)The risk or severity of adverse effects can be increased when Pirarubicin is combined with Hepatitis B Vaccine (Recombinant).Approved, Withdrawn
Human rabies virus immune globulinThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Human rabies virus immune globulin.Approved
INGN 201The risk or severity of adverse effects can be increased when Pirarubicin is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Pirarubicin is combined with INGN 225.Investigational
Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Pirarubicin is combined with Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated).Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Pirarubicin.Experimental
LeflunomideThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Leflunomide.Approved, Investigational
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Pirarubicin.Experimental
NatalizumabThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Natalizumab.Approved, Investigational
OcrelizumabOcrelizumab may increase the immunosuppressive activities of Pirarubicin.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Pirarubicin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Pirarubicin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Pirarubicin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Pirarubicin.Experimental
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Pirarubicin.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Pirarubicin.Experimental
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Rabies virus inactivated antigen, A.Approved, Investigational
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Pirarubicin.Approved, Investigational
RindopepimutThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Rindopepimut.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Pirarubicin.Approved
Rotavirus VaccineThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Rotavirus Vaccine.Approved
Rubella virus vaccineThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Rubella virus vaccine.Approved, Investigational
Salmonella typhi ty2 vi polysaccharide antigenThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Salmonella typhi ty2 vi polysaccharide antigen.Approved
Salmonella typhi ty21a live antigenThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Salmonella typhi ty21a live antigen.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Pirarubicin.Approved, Investigational
SRP 299The risk or severity of adverse effects can be increased when Pirarubicin is combined with SRP 299.Investigational
TacrolimusTacrolimus may increase the immunosuppressive activities of Pirarubicin.Approved, Investigational
TecemotideThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Tecemotide.Investigational
TG4010The risk or severity of adverse effects can be increased when Pirarubicin is combined with TG4010.Investigational
TofacitinibPirarubicin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Pirarubicin.Approved, Investigational
Typhoid VaccineThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Typhoid Vaccine.Approved
Varicella Zoster Vaccine (Live/Attenuated)The risk or severity of adverse effects can be increased when Pirarubicin is combined with Varicella Zoster Vaccine (Live/Attenuated).Approved
Yellow Fever VaccineThe risk or severity of adverse effects can be increased when Pirarubicin is combined with Yellow Fever Vaccine.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D01885
PubChem Compound
11296583
PubChem Substance
347828009
ChemSpider
9471567
ChEBI
94770
ChEMBL
CHEMBL2354444
Wikipedia
Pirarubicin
ATC Codes
L01DB08 — Pirarubicin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingPreventionBladder Recurrence / Nephroureterectomy / Upper Tract Urothelial Carcinoma1
2RecruitingPreventionBladder Recurrence / Upper Tract Urothelial Carcinoma1
2RecruitingTreatmentAntineoplastic Combined Chemotherapy Protocols1
2RecruitingTreatmentIntravesical Instillation1
2Unknown StatusTreatmentLymphoblastic Leukemia, Acute1
2, 3Not Yet RecruitingTreatmentHepatocellular,Carcinoma1
2, 3RecruitingTreatmentOverall Survival / Progression-free Survival / Toxicity1
3CompletedTreatmentNeoplasms, Breast1
3RecruitingTreatmentHepatocellular,Carcinoma1
4RecruitingTreatmentCancer, Breast1

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 Solubility0.301 mg/mLALOGPS
logP2.06ALOGPS
logP2.05ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area204.3 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity157.38 m3·mol-1ChemAxon
Polarizability64.85 Å3ChemAxon
Number of Rings6ChemAxon
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 / Anthraquinones / O-glycosyl compounds / Tetralins / Anisoles / Aryl ketones / Alkyl aryl ethers / Oxanes / Monosaccharides
show 11 more
Substituents
Anthracycline / Anthracyclinone-skeleton / Aminoglycoside core / Tetracenequinone / 9,10-anthraquinone / 1,4-anthraquinone / Anthracene / Glycosyl compound / O-glycosyl compound / Tetralin
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on August 25, 2016 16:58 / Updated on July 02, 2018 20:52