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Pirarubicin

CAT: 0013-GTR19161648-06Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161648-06Size:25 mg
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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. (In Vitro) :Pirarubicin is a topoisomerase II inhibitor. Pirarubicin shows inhibitory activities against M5076 and Ehrlich cells, with IC50s of 0.366 and 0.078 μM, respectively. The cytotoxicity of Pirarubicin toward M5076 cells is lower than toward Ehrlich cells, and this is due to the much lower expression of topoisomerase II in M5076 cells than in Ehrlich cells. Pirarubicin (2.5, 5, 10 μg/mL) significantly induces autophagy in a dose dependent manner in bladder cancer (T24, EJ, 5637, J82 and UM-UC-3) cells. Furthmore, Pirarubicin (5 μg/mL) induces apoptosis through inhibition of mTOR/p70S6K/4E-BP1 in bladder cancer cells, and this effect is enhanced by inhibition of autophagy. (In Vivo) :Pirarubicin (18 mg/kg, i.v.) significantly elevates serum level of BNP, CK-MB, CTnT, LDH, and MDA compared with those in the control group in acute cardiac toxicity rats. Pirarubicin also lowers heart rate, and depresses R-wave voltage, and prolongation of QT intervals in the acute cardiac toxicity model.
CAS Number
72496-41-4
Product Name Alternative
Tepirubicin | Tetrahydropyranyl-Doxorubicin | THP-Adriamycin | THP-Doxorubicin
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO:7 mg/mL (11.15 mM) ; Ethanol:<1 mg/mL (<1 mM) ; Water:<1 mg/mL (<1 mM)
Smiles
O=C1C2=C (O) C (C[C@] (C (CO) =O) (O) C[C@@H]3O[C@H]4C[C@H] (N) [C@H] (O[C@H]5CCCCO5) [C@H] (C) O4) =C3C (O) =C2C (C6=C1C=CC=C6OC) =O
Molecular Formula
C32H37NO12
Molecular Weight
627.64
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(8S,10S) -10- (((2R,4S,5S,6S) -4-amino-6-methyl-5- (((S) -tetrahydro-2H-pyran-2-yl) oxy) tetrahydro-2H-pyran-2-yl) oxy) -6,8,11-trihydroxy-8- (2-hydroxyacetyl) -1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

Chemical Information

Pirarubicin

Pirarubicin is an anthracycline that is doxorubicin in which the hydroxy group at position 4' is replaced by a (2R)-tetrahydro-2H-pyran-2-yloxy group. It has a role as an antineoplastic agent and a cardiotoxic agent. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of p-quinones, a deoxy hexoside, a member of oxanes, an aminoglycoside, an anthracycline, a member of tetracenequinones and a monosaccharide derivative. It is functionally related to a doxorubicin.

CAS Number72496-41-4
PubChem CID11296583
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
Molecular FormulaC32H37NO12
Molecular Weight627.6
XLogP2.7
Topological Polar Surface Area204
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Heavy Atom Count45
Formal Charge0
Complexity1120
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)O[C@@H]6CCCCO6
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-YXRRJAAWSA-N
Chemical Structure
2D Structure
2D structure of Pirarubicin
CAS: 72496-41-4
CID: 11296583
Formula: C32H37NO12
MW: 627.6
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight627.6
XLogP32.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Exact Mass627.23157562
Monoisotopic Mass627.23157562
Topological Polar Surface Area204 Ų
Heavy Atom Count45
Formal Charge0
Complexity1120
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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