Pirarubicin

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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 Number	72496-41-4
PubChem CID	11296583
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 Formula	C32H37NO12
Molecular Weight	627.6
XLogP	2.7
Topological Polar Surface Area	204
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Heavy Atom Count	45
Formal Charge	0
Complexity	1120

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

CAS: 72496-41-4

CID: 11296583

Formula: C32H37NO12

MW: 627.6

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	627.6
XLogP3	2.7
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Exact Mass	627.23157562
Monoisotopic Mass	627.23157562
Topological Polar Surface Area	204 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	1120
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
HY-13725-01	Pirarubicin

Pirarubicin

Chemical Information

Alternative Products

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