Home Aminos 5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-

5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-

CAS No.:
95343-20-7
Catalog Number:
AG01DPZ4
Molecular Formula:
C32H38ClNO12
Molecular Weight:
664.0966
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
98%
1 week
United States
$140
- +
50mg
98%
1 week
United States
$390
- +
100mg
98%
1 week
United States
$585
- +
Product Description
Catalog Number:
AG01DPZ4
Chemical Name:
5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-
CAS Number:
95343-20-7
Molecular Formula:
C32H38ClNO12
Molecular Weight:
664.0966
MDL Number:
MFCD01713157
IUPAC Name:
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
InChI:
InChI=1S/C32H37NO12.ClH/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;1H/t14-,17-,19-,21+,22-,31+,32-;/m0./s1
InChI Key:
ZPHYPKKFSHAVOE-YZIXBPQXSA-N
SMILES:
OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@@H]([C@@H](O2)C)O[C@@H]2CCCCO2)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC.Cl
UNII:
E7V83174BE
Properties
Complexity:
1120  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
0
Exact Mass:
663.208g/mol
Formal Charge:
0
Heavy Atom Count:
46  
Hydrogen Bond Acceptor Count:
13  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
664.101g/mol
Monoisotopic Mass:
663.208g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
204A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
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Characterization and pharmacokinetics of a novel pirarubicin liposome powder. Drug development and industrial pharmacy 20101001
A pilot study of combination chemotherapy with paclitaxel, pirarubicin, and carboplatin (TPC) for endometrial carcinoma. International journal of clinical oncology 20101001
[Analysis of the risk factors for vascular pain induced by the administration of pirarubicin]. Gan to kagaku ryoho. Cancer & chemotherapy 20101001
[Clinical observation of transarterial chemoembolization combined with sorafenib for advanced hepatocellular carcinoma]. Zhonghua zhong liu za zhi [Chinese journal of oncology] 20100901
In vitro and in vivo evaluation of tumor targeting styrene-maleic acid copolymer-pirarubicin micelles: Survival improvement and inhibition of liver metastases. Cancer science 20100801
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Studying the interaction of pirarubicin with DNA and determining pirarubicin in human urine samples: combining excitation-emission fluorescence matrices with second-order calibration methods. Journal of fluorescence 20091101
Combined arterial infusion and stent implantation compared with metal stent alone in treatment of malignant gastroduodenal obstruction. Cardiovascular and interventional radiology 20090901
Investigation on the interactions between pirarubicin and phospholipids. Biophysical chemistry 20090801
Use of intra-arterial chemotherapy and embolization before limb salvage surgery for osteosarcoma of the lower extremity. Cardiovascular and interventional radiology 20090701
Pilot study of transarterial chemoembolization with pirarubicin and amiodarone for unresectable hepatocellular carcinoma. American journal of clinical oncology 20090601
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Diagnosing the location of carcinoma in situ (CIS) of the urinary bladder using pirarubicin hydrochloride. Urologia internationalis 20050101
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Selective intra-arterial chemoembolization of pelvic and spine bone metastases. European radiology 20041001
Concurrent chemoradiotherapy with pirarubicin and 5-fluorouracil for resectable oral and maxillary carcinoma. Acta oto-laryngologica. Supplementum 20041001
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[Neoadjuvant chemotherapy for primary breast cancer]. Zhonghua zhong liu za zhi [Chinese journal of oncology] 20040801
[Intravesial instillation of recombination interferon-alpha and pirarubicin in the prophylaxis of local recurrence after resection of the superficial bladder cancer]. Ai zheng = Aizheng = Chinese journal of cancer 20040701
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Optimal strategy of preoperative transcatheter arterial chemoembolization for hepatoblastoma. Surgery today 20040101
The activity of latent benzoperimidine esters to inhibit P-glycoprotein and multidrug resistance-associated protein 1 dependent efflux of pirarubicin from several lines of multidrug resistant tumor cells. Cancer detection and prevention 20040101
Multimodal therapy with intravenous biweekly leucovorin, 5-fluorouracil and irinotecan combined with hepatic arterial infusion pirarubicin in non-resectable hepatic metastases from colorectal cancer (a European Association for Research in Oncology trial). Annals of oncology : official journal of the European Society for Medical Oncology 20031001
Doxorubicin and two of its analogues are preferential inducers of homologous recombination compared with mutational events in somatic cells of Drosophila melanogaster. Mutation research 20030805
Functional study of intracellular P-gp- and MRP1-mediated pumping of free cytosolic pirarubicin into acidic organelles in intrinsic resistant SiHa cells. Canadian journal of physiology and pharmacology 20030801
[Nephrogenic adenoma of the bladder treated with cystectomy to control severe irritative symptoms: a case report]. Hinyokika kiyo. Acta urologica Japonica 20030801
Rhodamine B as a mitochondrial probe for measurement and monitoring of mitochondrial membrane potential in drug-sensitive and -resistant cells. Journal of biochemical and biophysical methods 20030731
Pirarubicin is taken up by a uridine-transportable sodium-dependent concentrative nucleoside transporter in Ehrlich ascites carcinoma cells. Cancer chemotherapy and pharmacology 20030601
Induction chemotherapy for breast carcinoma: predictive markers and relation with outcome. International journal of oncology 20030601
Hepatic arterial infusion using pirarubicin combined with systemic chemotherapy: a phase II study in patients with nonresectable liver metastases from colorectal cancer. Annals of oncology : official journal of the European Society for Medical Oncology 20030601
Cloning and functional study of a novel human metallothionein-I isoform induced by paraquat. Biochemical and biophysical research communications 20030502
In vitro study of the compatibility of tris-acryl gelatin microspheres with various chemotherapeutic agents. Journal of vascular and interventional radiology : JVIR 20030501
[Intravesical instillation of pirarubicin (THP) together with polyvinylpyrrolidone (PVP) in the prevention of postoperative recurrence of superficial bladder cancer]. Ai zheng = Aizheng = Chinese journal of cancer 20030401
Liver metastasis of pancreatic cancer managed by intra-arterial infusion chemotherapy combined with degradable starch microspheres. International journal of clinical oncology 20030401
[Severe type of Epstein-Barr virus associated hemophagocytic syndrome successfully treated with T-COP-E and splenectomy]. Nihon Rinsho Men'eki Gakkai kaishi = Japanese journal of clinical immunology 20030401
Regression of refractory rhabdomyosarcoma after allogeneic stem-cell transplantation. Pediatric hematology and oncology 20030301
[Preoperative concurrent chemoradiotherapy with intra-arterial infusion of pirarubicin and continuous intravenous instillation of 5-fluorouracil for resectable advanced head and neck squamous cell carcinoma]. Gan to kagaku ryoho. Cancer & chemotherapy 20030301
Preparation and pharmacokinetics of pirarubicin loaded dehydration-rehydration vesicles. International journal of pharmaceutics 20030218
Prospective comparison of 18F-FDG PET with conventional imaging modalities (MRI, CT, and 67Ga scintigraphy) in assessment of combined intraarterial chemotherapy and radiotherapy for head and neck carcinoma. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20030201
Advanced ureteral cancer with complete remission achieved by taxan containing systemic chemotherapy. International journal of urology : official journal of the Japanese Urological Association 20030201
[Paclitaxel and carboplatin with or without pirarubicin (THP-ADR) as first line chemotherapy in elderly patients]. Gan to kagaku ryoho. Cancer & chemotherapy 20030201
FDG-PET for prediction of tumour aggressiveness and response to intra-arterial chemotherapy and radiotherapy in head and neck cancer. European journal of nuclear medicine and molecular imaging 20030101
Clinical outcome of conservative therapy for stage T1, grade 3 transitional cell carcinoma of the bladder. International journal of urology : official journal of the Japanese Urological Association 20030101
[Weekly administration of paclitaxel and pirarubicine for recurrent breast cancer]. Gan to kagaku ryoho. Cancer & chemotherapy 20030101
In vitro polyvinylformaldehyde particle compatibility with chemotherapeutic drugs used for chemoembolization therapy. Cardiovascular and interventional radiology 20030101
[A case of recurrent breast cancer with carcinomatous pleurisy successfully treated with combined chemoendocrine-therapy of CTF (CPA, THP and 5-FU) and anastrozole following instillation therapy 12 years after radical mastectomy]. Gan to kagaku ryoho. Cancer & chemotherapy 20021201
Comparative binding of antitumor drugs to DNA containing the telomere repeat sequence. Experimental & molecular medicine 20021130
Correlation between nuclear action of anthracycline anticancer agents and their binding affinity to the proteasome. International journal of oncology 20021101
Intensified chemotherapy increases the survival rates in patients with stage 4 neuroblastoma with MYCN amplification. Journal of pediatric hematology/oncology 20021101
Relation between MDR1 mRNA levels, resistance factor, and the efficiency of P-glycoprotein-mediated efflux of pirarubicin in multidrug-resistant K562 sublines. Canadian journal of physiology and pharmacology 20021101
The role of the proteasome in apoptosis induced by anthracycline anticancer agents. International journal of oncology 20020601
Pirarubicin-based versus doxorubicin-based osteosarcoma chemotherapy. The Annals of pharmacotherapy 20020601
Outcome of hepatoblastoma treated with the JPLT-1 (Japanese Study Group for Pediatric Liver Tumor) Protocol-1: A report from the Japanese Study Group for Pediatric Liver Tumor. Journal of pediatric surgery 20020601
Doxorubicin enhances TRAIL-induced apoptosis in prostate cancer. International journal of oncology 20020501
Randomized study of single early instillation of (2'R)-4'-O-tetrahydropyranyl-doxorubicin for a single superficial bladder carcinoma. Cancer 20020501
Relationships between the in vitro cytotoxicity and transport characteristics of pirarubicin and doxorubicin in M5076 ovarian sarcoma cells, and comparison with those in Ehrlich ascites carcinoma cells. Cancer chemotherapy and pharmacology 20020301
High-dose chemotherapy with peripheral blood stem cell transplantation for advanced testicular cancer. International journal of urology : official journal of the Japanese Urological Association 20020301
Apoptosis in young rats with adriamycin-induced cardiomyopathy--comparison with pirarubicin, a new anthracycline derivative. Pediatric research 20020201
Locally advanced mucinous carcinoma of the breast with sudden growth acceleration: a case report. Japanese journal of clinical oncology 20020201
Scintigraphic prediction of response to chemotherapy in patients with breast cancer: Technetium 99m-tetrofosmin and thallium-201 dual single photon emission computed tomography. International journal of oncology 20020101
[A 5'-DFUR + CPA + THP therapy that was effective for paclitaxel-refractory pulmonary metastasis of breast cancer--a case report]. Gan to kagaku ryoho. Cancer & chemotherapy 20020101
[A case of regionally metastatic pure squamous cell carcinoma of the urinary bladder successfully treated with radical chemoradiotherapy]. Hinyokika kiyo. Acta urologica Japonica 20020101
Breast-conservation treatment for bilateral breast cancer in five Japanese women. Oncology reports 20020101
Circadian chemotherapy for gynecological and genitourinary cancers. Chronobiology international 20020101
Interferon-alpha therapy following autologous peripheral blood stem cell transplantation for adult T cell leukemia/lymphoma. Acta haematologica 20020101
Docetaxel enhances the cytotoxicity of anthracyclines by increasing intracellular drug accumulation. Oncology reports 20020101
Superior outcome of infant acute myeloid leukemia with intensive chemotherapy: results of the Japan Infant Leukemia Study Group. Blood 20011215
Increased cytotoxicity and stability of Lipiodol-pirarubicin emulsion compared to classical doxorubicin-Lipiodol: potential advantage for chemoembolization of unresectable hepatocellular carcinoma. Anti-cancer drugs 20011101
Myeloid-positive T cell acute leukemia after treatment of infantile neuroblastoma. Medical and pediatric oncology 20011101
Spectroscopic studies on iron complexes of different anthracyclines in aprotic solvent systems. Inorganic chemistry 20011008
Structure-activity relationships and optimisation of the selective MDR modulator 2-(3,4-dimethoxyphenyl)-5-(9-fluorenylamino)-2-(methylethyl) pentanenitrile and its N-methyl derivative. Bioorganic & medicinal chemistry 20011001
[A case of malignant pericardial effusion due to breast cancer successfully controlled by intrapericardial chemotherapy using pirarubicin]. Gan to kagaku ryoho. Cancer & chemotherapy 20011001
Improved survival of children with advanced neuroblastoma treated by intensified therapy including myeloablative chemotherapy with stem cell transplantation: a retrospective analysis from the Tohoku Neuroblastoma Study Group. The Tohoku journal of experimental medicine 20011001
Fluorescent verapamil analogue for monitoring acidic intracellular organelles in multidrug resistant and sensitive cells. Chemico-biological interactions 20010731
Prognostic factors for survival and bladder recurrence in transitional cell carcinoma of the upper urinary tract. International journal of urology : official journal of the Japanese Urological Association 20010701
[CHF arising after low dose THP-COP chemotherapy in an elderly patient with malignant lymphoma]. Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics 20010701
[Multi-institutional cooperative study on combination chemotherapy with THP, CDDP and 5-FU for squamous cell carcinoma of the head and neck]. Gan to kagaku ryoho. Cancer & chemotherapy 20010601
[Prophylactic effect of pirarubicin (THP) on postoperative recurrence of superficial bladder cancer in terms of intravesical retention time]. Hinyokika kiyo. Acta urologica Japonica 20010501
[Fundamental study of combination chemotherapy with THP, 5-FU and CDDP for human KB carcinoma cell line and its multidrug resistant cell line KB-C1--usefulness of treatment with 5-FU preceding CDDP]. Gan to kagaku ryoho. Cancer & chemotherapy 20010401
Transport of new non-cross-resistant antitumor compounds of the benzoperimidine family in multidrug resistant cells. European journal of pharmacology 20010216
Two patients with N3 bladder cancer successfully treated by internal iliac arterial infusion chemotherapy and irradiation: case reports. American journal of clinical oncology 20010201
[Therapy-related myeloid leukemia following platinum-based chemotherapy for ovarian cancer]. [Rinsho ketsueki] The Japanese journal of clinical hematology 20010201
Outcome prediction by molecular detection of minimal residual disease in bone marrow for advanced neuroblastoma. Medical and pediatric oncology 20010101
Skin rash in the hypogastric region during a regional chemotherapy for bladder carcinoma: CT and scintigraphic demonstration of a potential collateral pathway between the internal iliac and inferior epigastric arteries. European radiology 20010101
Docetaxel enhances the cytotoxicity of tetrahydropyranyladriamycin in a sequence-dependent manner. Anticancer research 20010101
Resistant mechanisms of anthracyclines--pirarubicin might partly break through the P-glycoprotein-mediated drug-resistance of human breast cancer tissues. Breast cancer (Tokyo, Japan) 20010101
In vitro chemosensitivity of human soft tissue sarcoma. Anticancer research 20010101
[Combination effect of pirarubicin, ifosfamide, and vincristine sulfate in the treatment of advanced synovial sarcoma--report of a case]. Gan to kagaku ryoho. Cancer & chemotherapy 19950901
Phase II clinical and pharmacological study of pirarubicin in combination with 5-fluorouracil and cyclophosphamide in metastatic breast cancer. Clinical cancer research : an official journal of the American Association for Cancer Research 19950701
[Ischemic hepatitis due to anthracycline-induced cardiac insufficiency in a patient with acute myelocytic leukemia (M0)]. [Rinsho ketsueki] The Japanese journal of clinical hematology 19950101
Comparison of cardiotoxicity of pirarubicin, epirubicin and doxorubicin in the rat. Drugs under experimental and clinical research 19940101
[Sciatic nerve paralysis following intraarterial chemotherapy for bladder cancer: reports of two cases]. Hinyokika kiyo. Acta urologica Japonica 19930801
[Intrapleural administration of pirarubicin in the treatment of malignant pleural effusion]. Gan to kagaku ryoho. Cancer & chemotherapy 19910901
New anthracycline antitumor antibiotics. Critical reviews in oncology/hematology 19910101
A phase I study of 4'-0-tetrahydropyranyladriamycin. Clinical pharmacology and pharmacokinetics. Cancer 19901115
Phase I-II study on weekly administration of pirarubicin in patients with metastatic breast cancer. American journal of clinical oncology 19900101
[THP-adriamycin: status of the clinical development of a new anthracycline in France]. Pathologie-biologie 19900101
Activity of pirarubicin (4'-0-tetrahydropyranyladriamycin) in malignant mesothelioma. Cancer 19890315
An oriented phase II trial of THP-adriamycin in breast carcinoma. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 19860101
[Acute cardiotoxicity of anthracyclines--analysis by using Holter ECG]. Gan to kagaku ryoho. Cancer & chemotherapy 19840401
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