(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-(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

• ChemBase ID: 72657
• Molecular Formular: C32H37NO12
• Molecular Mass: 627.63568
• Monoisotopic Mass: 627.23157563
• SMILES: [C@@H]1([C@H]([C@H](C[C@@H](O1)O[C@@H]1c2c(C[C@](C1)(C(=O)CO)O)c(c1c(c2O)C(=O)c2c(C1=O)cccc2OC)O)N)OC1OCCCC1)C
• Canonical SMILES: OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@@H]([C@@H](O2)C)OC2CCCCO2)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• 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
• InChIKey: KMSKQZKKOZQFFG-NCXNULAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-(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
• IUPAC Traditional name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: THP; Pirarubicin; THP-Adriamycin; Pirarubicin

Database IDs

• CAS Number: 72496-41-4
• MDL Number: MFCD00869742
• PubChem SID: 162037582
• PubChem CID: 6917695

CALCULATED PROPERTIES

• Acid pKa: 9.478123
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 0.1203337
• LogD (pH = 7.4): 1.3603758
• Log P: 2.5154042
• Molar Refractivity: 157.3784 cm^3
• Polarizability: 61.92432 Å^3
• Polar Surface Area: 204.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: topoisomerase

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: Free Base
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C32H37NO12

DETAILS

Selleck Chemicals - S1393

Research Area: Cancer
Biological Activity:
Pirarubicin is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines. [1,2]References on Pirarubicin[1] http://www.cancer.gov/drugdictionary/?CdrID=38775, , [2] http://en.wikipedia.org/wiki/Pirarubicin, ,

Sigma Aldrich - P8624

Biochem/physiol Actions
Anthracycline antibiotic that is an analog of doxorubicin. Antineoplastic. Pirarubicin is transported into cells vial a sodium-dependent nucleoside transporter.1,2 It is used to intercalate DNA and inhibit the activity of topoisomerase II and induce DNA crosslinking.
Application
Pirarubicin, an anthracycline antibiotic, is an anticancer drug. Pirarubicin is used to study synergistic cytotoxicity and apoptosis of cancer cells1,2. It is used to study how to protect multi-drug resistance cells from anthracycline induced cytotoxicity3.

REFERENCES

• http://en.wikipedia.org/wiki/Pirarubicin