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P8624

Sigma-Aldrich

Pirarubicin

≥95% (HPLC)

Synonym(s):

THP

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About This Item

Empirical Formula (Hill Notation):
C32H37NO12
CAS Number:
72496-41-4
Molecular Weight:
627.64
MDL number:
MFCD00869742
UNSPSC Code:
51281913
PubChem Substance ID:
329820330
NACRES:
NA.85

Quality Level

200

Assay

≥95% (HPLC)

form

powder

solubility

ethanol: soluble 25 mg/mL

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes
enzyme | inhibits

shipped in

wet ice

storage temp.

2-8°C

SMILES string

COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](OC6CCCCO6)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO

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-NCXNULAVSA-N

Application

Pirarubicin is used to study synergistic cytotoxicity and apoptosis of cancer cells. It is used to study how to protect multi-drug resistance cells from anthracycline induced cytotoxicity.

Biochem/physiol Actions

Pirarubicin, an anthracycline antibiotic that is an analog of doxorubicin, is an antineoplastic drug. Pirarubicin is transported into cells via a sodium-dependent nucleoside transporter.1,2 It is used to intercalate DNA and inhibit the activity of topoisomerase II and induce DNA crosslinking.

Packaging

10mg,25mg

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H350,H360FD

Hazard Classifications

Carc. 1B - Muta. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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X X Wu et al.
Cancer research, 60(11), 2912-2918 (2000-06-13)
Anti-Fas monoclonal antibody (mAb) kills Fas-expressing cells by apoptosis. Several anticancer agents also mediate apoptosis and may share common intracellular pathways leading to apoptosis with Fas. Thus, we reasoned that combination treatment of drug-resistant cells with anti-Fas mAb and drugs
Akihiro Ito et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(11), 1422-1427 (2013-03-06)
We evaluated the efficacy of a single early intravesical instillation of pirarubicin (THP) in the prevention of bladder recurrence after nephroureterectomy for upper urinary tract urothelial carcinoma (UUT-UC). From December 2005 to November 2008, 77 patients clinically diagnosed with UUT-UC
Romana J R Yanez et al.
PloS one, 12(8), e0183177-e0183177 (2017-08-12)
High-risk human papillomaviruses (hr-HPVs) cause cervical cancer, the fourth most common cancer in women worldwide. A HPV-16 candidate therapeutic vaccine, LALF32-51-E7, was developed by fusing a modified E7 protein to a bacterial cell-penetrating peptide (LALF): this elicited both tumour protection
Y Mizutani et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 5(9), 2605-2612 (1999-09-28)
Resistance to conventional anticancer chemotherapeutic agents remains one of the major problems in the treatment of bladder cancer. Hence, new therapeutic modalities are necessary to treat the drug-resistant cancers. Apo-2 ligand (Apo-2L) is member of the tumor necrosis factor ligand
R Belhoussine et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 46(12), 1369-1376 (1998-11-17)
We used confocal microspectrofluorometry to investigate intracellular distribution of pirarubicin or THP-DOX in parental K562, CEM, and LR73 tumor cells and their corresponding multidrug-resistant (MDR) strains. Each spectrum of a recorded image was considered as a combination of cell autofluorescence
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