Therarubicin

Base Information

• Chemical Name: Therarubicin
• CAS No.: 72496-41-4
• Molecular Formula: C₃₂H₃₇NO₁₂
• Molecular Weight: 627.645
• NCI Thesaurus Code: C1197
• Nikkaji Number: J22.798F
• Wikipedia: Pirarubicin
• Mol file: 72496-41-4.mol

Synonyms:4'-O-tetrahydropyranyladriamycin;4'-O-tetrahydropyranyldoxorubicin;4'-O-tetrapyranyldoxorubicin;pirarubicin;pirarubicin hydrochloride;Théprubicine;thepirubicin;Theprubicin;therarubicin;THP-ADM;THP-adriamycin;THP-DOX;THP-doxorubicin

Chemical Property of Therarubicin

Chemical Property:

• Appearance/Colour: Red crystalline powder
• Vapor Pressure: 1.51E-29mmHg at 25°C
• Melting Point: 188-192 °C (dec.)
• Refractive Index: 1.67
• Boiling Point: 834.659 °C at 760 mmHg
• PKA: 7.35±0.60(Predicted)
• Flash Point: 458.586 °C
• PSA: 204.30000
• Density: 1.519 g/cm³
• LogP: 2.25250
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble25mg/mL
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 627.23157562
• Heavy Atom Count: 45
• Complexity: 1120

Purity/Quality:

99% ^*data from raw suppliers

Pirarubicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OC6CCCCO6
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OC6CCCCO6
• Recent ClinicalTrials: Adjuvant Albumin-bound Paclitaxel Versus Taxanes in Breast Cancer: a Real-world Study
• Recent NIPH Clinical Trials: JCOG1403: Phase III trial of a single early intravesical instillation of pirarubicin in the prevention of bladder recurrence after nephroureterectomy for upper tract urothelial carcinoma
• Description: Pirarubicin is a new anthracycline anticancer agent structurally related to doxorubicin. In acute leukemia, non-Hodgkin’s lymphoma, breast and ovariail carcinoma, pirarubicin is reportedly superior to doxorubicin and better tolerated. Its major side-effect appears to be myelosuppression, mainly in the form of leucopenia, which is potentially dose-limiting.
• Uses: Structural analog of Doxorubicin. Antineoplastic. Structural analog of Doxorubicin. Antineoplastic

Technology Process of Therarubicin

There total 2 articles about Therarubicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 10-[(2R,4R,5S,6S)-4-Amino-6-methyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-6,8,11-trihydroxy-8-(2-hydroxy-acetyl)-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione (70287-21-7,72496-41-4,97858-99-6,123354-98-3)

Guidance literature:

Bis(O-Tetrahydropyranyl)-Derivaten IVa und IVb, TosOH;

DOI:10.7164/antibiotics.32.1082

Reference yield:

→ (8S,10S)-10-[(2R,4R,5S,6S)-4-Amino-6-methyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-6,8,11-trihydroxy-8-(2-hydroxy-acetyl)-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione (70287-21-7,72496-41-4,97858-99-6,123354-98-3)

Guidance literature:

Bis(O-tetrahydropyranyl)-Derivaten IVa, IVb mit TosOH;

DOI:10.7164/antibiotics.32.1082

Refernces