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Pirarubicin

Pirarubicin structure

CAS No:
72496-41-4
Formula:
C32H37NO12
Chemical Name:
Pirarubicin
Synonyms:
5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-,(8S,10S)-;5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,[8S-[8α,10α(S*)]]-;5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,(8S,10S)-;(8S,10S)-10-[[3-Amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione;4′-O-Tetrahydropyranyladriamycin;THP-Adriamycin;(2′′R)-4′-O-Tetrahydropyranyladriamycin;Pirarubicin;Pinorubicin;(2′′R)-4′-O-Tetrahydropyranyldoxorubicin;Therarubicin;70259-49-3
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Pirarubicin is an anthracycline antibiotics, acts as a topoisomerase II inhibitor, and is a widely used for treatment of various cancers, in particular, solid tumors.

Pirarubicin Basic Attributes

Molecular Weight：

627.64

Exact Mass：

627.64

DSSTox ID：

DTXSID2046755

ATC Code：

L - Antineoplastic and immunomodulating agents

Characteristics

PSA：

204.30000

XLogP3：

3.85

Appearance：

Red crystalline powder

Density：

1.5±0.1 g/cm3

Melting Point：

184-186 °C (decomp)

Boiling Point：

834.7±65.0 °C at 760 mmHg

Flash Point：

458.6±34.3 °C

Refractive Index：

1.671

Water Solubility：

ethanol: soluble 25mg/mL

Storage Conditions：

2-8°C

Toxicity：

LD50 i.v. in mice: 27.8 mg/kg (Umezawa, 1979)

Specific rotation：

D25 +175 ±25° (c = 0.2 in CHCl3)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-37/39

RTECS Number：

QI9296000

Marks：

Drug Information

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

MeSH Entry Terms：

4'-O-tetrahydropyranyladriamycin

Pirarubicin Use and Manufacturing

Methods of Manufacturing

With doxorubicin (Adriarnycin) hydrochloride as raw material. 130 mg of doxorubicin hydrochloride was dissolved in 10 ml of dry N, N-dimethylformamide and reacted with 2 ml of 3, 4-dihydro-2H-pyran at room temperature for 47 hours under the action of catalyst p-toluenesulfonic acid. Separated with a thin layer of prepared silica gel to obtain 14, 4'-bis(O-tetrahydropyranyl) doxorubicin. Then, it was reacted with 0.005mol/L p-toluenesulfonic acid in methanol for 1h at room temperature, and 14-O-tetrahydropyranyl group was removed to obtain pirarubicin.

Uses

Structural analog of Doxorubicin. Antineoplastic

Computed Properties

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
Heavy Atom Count:45
Complexity:1120
Undefined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

No specific description provided

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Pirarubicin

Pirarubicin
Manufacturer	Zhejiang Hisun Pharmaceutical Co., Ltd.

Registered Holders

Zhejiang Hisun Pharmaceutical Co., Ltd.

China
Active
ShenZhen Main Luck Pharmaceuticals Inc

China
Active
Guangzhou Greensyn Pharma Co., Ltd.

China
Inactive

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