Pirarubicin

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Pirarubicin
Category Antibiotics
Catalog number BBF-03937
CAS 72496-41-4
Molecular Weight 627.64
Molecular Formula C32H37NO12
Purity >98%

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BBF-03937 25 mg $199 In stock

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Description

Pirarubicin is an anthracycline antibiotic, and also a DNA/RNA synthesis inhibitor by intercalating into DNA and interacts with topoisomerase II, used as an antineoplastic agent.

Specification

Related CAS 95343-20-7 (hydrochloride)
Synonyms Theprubicin; CGH-869; CGH 869; CGH869
Storage Store at 2-8°C
IUPAC Name (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2S)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Canonical SMILES CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)OC6CCCCO6
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
InChI Key KMSKQZKKOZQFFG-HSUXVGOQSA-N

Properties

Appearance Red Crystalline Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 834.7°C at 760 mmHg
Melting Point 188-192°C (dec.)
Density 1.51 g/cm3
Solubility Soluble in ethanol

Reference Reading

1.[Peripheral T-Cell Lymphoma, Not Otherwise Specified Occurring After the Treatment of Relapsed Follicular Lymphoma].
Fukushima H, Inoue T, Ishi N, Okuno T, Son R, Soejima C, Horiuchi M, Ueda H, Yoshida M, Hagihara K, Kanashima H, Nakao T, Yamane T. Rinsho Byori. 2015 Sep;63(9):1029-34.
A 77-year-old-man was diagnosed with follicular lymphoma (FL), grade 3A. After six courses of R-THP-COP (rituximab, pirarubicin, cyclophosphamide, vincristine and prednisolone) therapy, he achieved complete remission (CR). He achieved a second CR after radiotherapy, a third CR after six courses of bendamustine /rituximab (BR) therapy, and a fourth CR after six courses of BR therapy. However 2 months after the last chemotherapy, his tumor progressed rapidly and he died. Autopsy results showed medium and large lymphoid cells with pleomorphic, irregular nuclei and prominent nucleoli infiltrated in multiple lymph nodes, the liver, the lung, and the spleen. The lymphoid cells were positive for CD3, CD8, granzymeB, TIA-1 and negative for CD4, CD20, CD79a, CD10, and CD56. Autopsy diagnosis was peripheral T-cell lymphoma, not otherwise specified. Occurrence of lymphoma in T-cell lineage should be considered, if the course of low-grade B-cell lymphomas, such as FL rapidly progresses.
2.Primary pineal rhabdomyosarcoma successfully treated by high-dose chemotherapy followed by autologous peripheral blood stem cell transplantation: case report.
Ishi Y1, Yamaguchi S1, Iguchi A2, Cho Y2, Ohshima J2, Hatanaka KC3, Takakuwa E3, Kobayashi H1, Terasaka S1, Houkin K1. J Neurosurg Pediatr. 2016 Mar 4:1-5. [Epub ahead of print]
Primary intracranial rhabdomyosarcoma is quite rare, and its prognosis is poor compared with that for rhabdomyosarcoma in other organs. The authors present a case of pineal rhabdomyosarcoma successfully managed with multimodal therapy including surgery, chemotherapy, radiation, and high-dose chemotherapy (HDC) followed by autologous peripheral blood stem cell transplantation (HDC/APBSCT). An 8-year-old girl presenting with headache and nausea was referred to the authors' institution. Computed tomography and MRI revealed a pineal tumor associated with obstructive hydrocephalus. Subsequently, an emergent endoscopic tumor biopsy and third ventriculostomy were performed. The patient's symptoms immediately improved. The most likely pathological diagnosis was embryonal rhabdomyosarcoma. Chemotherapy with etoposide, cyclophosphamide, cisplatin, pirarubicin, ifosfamide, actinomycin D, and vincristine was followed by a second-look operation and whole-brain and craniospinal radiation.
3.[Langerhans cell sarcoma developing acute myeloid leukemia after achieving complete response by THP-COP].
Hamaguchi K1, Hashimoto A, Fujimi A, Kanisawa Y, Shibata T, Nakajima C, Hayasaka N, Yamada S, Okuda T, Minami S, Kamihara Y, Ohshima K, Kato J. Rinsho Ketsueki. 2015 Dec;56(12):2456-61. doi: 10.11406/rinketsu.56.2456.
An 86-year-old man presented with enlarged left submandibular, left inguinal, and superficial femoral lymph nodes. He was diagnosed with Langerhans cell sarcoma (LCS) on the basis of the histopathological findings of the left inguinal lymph node biopsy. In addition, laboratory examinations revealed normocytic normochromic anemia, and bone marrow aspiration and biopsy led to a diagnosis of idiopathic cytopenia of undetermined significance (ICUS). Because of the patient's age, he was administered a regimen of cyclophosphamide, pirarubicin, vincristine, and prednisolone (THP-COP), and achieved a partial response after six courses. However, he developed acute myeloid leukemia (AML) 11 months after completion of the THP-COP therapy, and received only supportive care until his death. LCS is an extremely rare and aggressive dendritic cell neoplasm. To the best of our knowledge, only 67 cases have been reported in the literature. There are case reports describing the concurrence of hematological malignancies.
4.DTC chemotherapy regimen is associated with higher incidence of premature ovarian failure in women of reproductive age with breast cancer.
Long JP1, Wan F, Zhang F, Zhou J, Don LF. Eur Rev Med Pharmacol Sci. 2016 Mar;20(6):1087-92.
OBJECTIVE: Different chemotherapy regimens may contribute differently to the development of Premature Ovarian Failure (POF) in women of reproductive age with breast cancer. Here we evaluated how two different chemotherapy regimens, CAF (tegafur + pirarubicin + ifosfamide) and DTC (docetaxel + pirarubicin + ifosfamide), affect the development of POF.

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