110267-81-7

Basic information

• Product Name: AMRUBICIN
• Synonyms: (7S,9S)-9-Acetyl-9-amino-7-[(2-deoxy--D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione;(7S)-9β-Amino-9-acetyl-7β-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxynaphthacene-5,12-dione;(7S,9S)-9-Acetyl-9-amino-7-(2-deoxy-β-D-erythro-pentopyranosyloxy)-6,11-dihydroxy-5,7,8,9,10,12-hexahydro-5,12-naphthacenedione;(7S,9S)-9-Amino-9-acetyl-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxynaphthacene-5,12-dione;Amurubicin;5,12-Naphthacenedione,9-acetyl-9-aMino-7-(2-deoxy-b-D-erythro-pentopyranosyl)oxy-7,8,9,10-tetrahydro-6,11-dihydroxy-,(7S,9S)-
• CAS NO: 110267-81-7
• Molecular Formula: C25H25NO9
• Molecular Weight: 483.47
• Product Categories: Carbohydrates & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 110267-81-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 172-1740C
• Boiling Point: 717.8 °C at 760 mmHg
• Flash Point: 387.9 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 1.26E-21mmHg at 25°C
• Refractive Index: 1.72
• PKA: 7.83±0.60(Predicted)
• CAS DataBase Reference: AMRUBICIN(CAS DataBase Reference)
• NIST Chemistry Reference: AMRUBICIN(110267-81-7)
• EPA Substance Registry System: AMRUBICIN(110267-81-7)

Safety Data

• Hazardous Substances Data: 110267-81-7(Hazardous Substances Data)

Usage

Description

Amrubicin is a synthetic anthracycline antibiotic with a molecular formula of C25H25NO9. It is a specific inhibitor of topoisomerase II and is used as an antineoplastic agent, particularly for the treatment of lung cancer. Amrubicin is structurally distinguishable from other anthracyclines by the amino group at the 9-position and its unique sugar moiety. It is a prodrug for the active metabolite, ambrucinol, and has a role as a topoisomerase II inhibitor, an antineoplastic agent, and a prodrug. Amrubicin is a quinone, a member of tetracenes, a methyl ketone, an anthracycline antibiotic, and a primary amino compound.

Uses

Used in Oncology:
Amrubicin is used as an antineoplastic agent for the treatment of small-cell lung cancer (SCLC). It inhibits DNA topoisomerase II, which plays a crucial role in the replication, transcription, and repair of DNA. By inhibiting this enzyme, Amrubicin interferes with the cancer cell's ability to replicate its DNA, ultimately leading to cell death.
Used in Pharmaceutical Industry:
Amrubicin is used as a synthetic anthracycline antibiotic in the pharmaceutical industry for the development of cancer treatments. Its unique structure and mechanism of action make it a valuable compound in the fight against various types of cancer, particularly lung cancer.
In April 2002, Amrubicin was approved in Japan for the treatment of non-small cell lung cancer and small cell lung cancer, further highlighting its importance in the field of oncology and pharmaceuticals.

Mode of action

Amrubicin (AMR), a third-generation anthracycline and potent topoisomerase II inhibitor that intercalates into DNA and inhibits the activity of topoisomerase II, resulting in inhibition of DNA replication, and RNA and protein synthesis, followed by cell growth inhibition and cell death. Amrubicin is structurally distinguishable from other anthracyclines by the amino group at the 9-position and its unique sugar moiety. This agent has demonstrated a higher level of anti-tumor activity than conventional anthracycline drugs without exhibiting any indication of the cumulative cardiac toxicity common to this class of compounds.

InChI:InChI=1/C25H25NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3/t14-,15+,16-,17?,25-/m0/s1

Upstream product

• 4258-01-9 1,3,4-tri-O-acetyl-2-deoxy-β-D-erythro-pentopyranose 
• 92395-41-0 (+)-9-amino-4-demethoxy-9-deoxo-daunomycinone 
• 110267-78-2 (4S,14S)-(+)-4-<1,1-(ethylenedioxy)ethyl>-4,5-dihydro-6,13-dihydroxy-4,14-methano-2-methyl-14H-anthra<3,2-f><1,3>oxazocine-7,12-dione 
• 86264-76-8 (R)-(-)-9-acetamido-9-<1,1-(ethylenedioxy)ethyl>-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 
• 104319-02-0 (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 
• 86264-55-3 (R)-(-)-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid 
• 110191-56-5 2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid 
• 86264-57-5 (R)-(-)-methyl 2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate 
• 86264-61-1 (R)-(-)-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 
• 110267-84-0 1-((R)-2-Amino-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-methanesulfinyl-ethanone 
• 99907-83-2 (R)-(-)-2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester 
• 99907-80-9 methyl 2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate 
• 110267-86-2 1-((R)-2-Amino-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethanone 
• 110267-85-1 N-[(R)-2-(2-Methanesulfinyl-acetyl)-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-acetamide 

Related news

AMRUBICIN (cas 110267-81-7) and carboplatin with pegfilgrastim in patients with extensive stage small cell lung cancer: A phase II trial of the Sarah Cannon Oncology Research Consortium08/09/2019

PurposeFirst-line treatment for patients with extensive-stage small cell lung cancer (SCLC) includes treatment with platinum-based combination chemotherapy. Amrubicin is a synthetic anthracycline with single-agent activity in relapsed/refractory SCLC. In an attempt to improve treatment efficacy,...detailed

Relevant articles and documents

A method for synthesizing ammonia supple ratio star

The invention discloses a synthetic method for amrubicin. R-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene is used as a raw material, and is subjected to acylation and cyclization with phthalic anhydride. 1,3-propanediol and derivatives thereof are used to protect carbonyl, and the protective group is liable to remove in a hydrolysis reaction. The amrubicin is prepared by a step of subjecting (+)-9-amino-4-demethoxy-9-deoxy-daunomycinone with 2-deoxy-3,4-di-O-acetyl-beta-D-erythro-pentapyranosyl-1,1,1-trichloroiminoacetate to a nucleoside-forming reaction to obtain (+)-9-amino-4-demethoxy-9-deoxy-7-O-(2-deoxy-3,4-di-O-acteyl-beta-D-erythro-pentapyranosyl) daunomycinone, and a step of removing acetyl. The synthetic method can avoid generation of isomers during a hydrolysis process effectively. The synthetic method has simple subsequent purification steps. The nucleoside-forming reaction can decrease the production cost effectively. The synthetic method is suitable for industrial applications.

Aminonaphthacene derivatives

9-Aminonaphthacene derivative having the formula: STR1 wherein R1 and R2 are both hydrogen atoms or either one of them is a hydrogen atom and the other is hydroxy group or methoxy group; R3 is acetyl group or 1-hydroxyethyl group; R4 is a hydrogen atom; R5 is a hydrogen atom, hydroxy group, lower alkanoyloxy group, amino group, halogen-substituted lower alkanoylamino group or morpholino group; R6 is a hydrogen atom, hydroxy group, lower alkanoyloxy group or tetrahydropyranyloxy group; R7 is a hydrogen atom or methyl group; R is a hydrogen atom; and n is zero or one, which is useful as anti-cancer chemical agents with lower toxicity and with little local irritation and is able to orally be applied.