ChemicalBook > CAS DataBase List > Lurbinectedin

Lurbinectedin

Product Name: Lurbinectedin
CAS No.: 497871-47-3
Chemical Name: Lurbinectedin
Synonyms: PM01183;PM 01183;PM-01183;Rubitidine;LURBINECTEDIN;Lurbinectidine;UNII-2CN60TN6ZS;D3-Lurbinectedin;Lubic alternative;Rupee substitution
CBNumber: CB82628057
Molecular Formula: C41H44N4O10S
Formula Weight: 784.88
MOL File: 497871-47-3.mol

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Lurbinectedin Property

Density: 1.55±0.1 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: Soluble in DMSO
form: Solid
pka: 9.79±0.40(Predicted)
color: White to light yellow
InChIKey: YDDMIZRDDREKEP-JUVYNUGVNA-N

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Biorbyt Ltd

Product number: orb573146
Product name: Lurbinectedin
Purity: >98%
Packaging: 5mg
Price: $2839
Updated: 2021/12/16

ChemScene

Product number: CS-6323
Product name: Lurbinectedin
Purity: 99.91%
Packaging: 2mg
Price: $3360
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb573146
Product name: Lurbinectedin
Purity: >98%
Packaging: 10mg
Price: $4173.5
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb573146
Product name: Lurbinectedin
Purity: >98%
Packaging: 25mg
Price: $5210.5
Updated: 2021/12/16

ChemScene

Product number: CS-6323
Product name: Lurbinectedin
Purity: 99.91%
Packaging: 100ug
Price: $550
Updated: 2021/12/16

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Lurbinectedin Chemical Properties,Usage,Production

Description

Lurbinectedin is a synthetic tetrahydropyrrolo [4, 3, 2-de]quinolin-8(1H)-one alkaloid analogue with potential antineoplastic activity. Lurbinectedin covalently binds to residues lying in the minor groove of DNA, which may result in delayed progression through S phase, cell cycle arrest in the G2/M phase and cell death. Lurbinectedin was approved for medical use in the United States in June 2020.

Uses

Lurbinectedin is being developed for the treatment of various cancers. It has been granted approval for treatment of metastatic small cell lung cancer.

Application

Lurbinectedin is indicated for the treatment of adult patients with metastatic small cell lung cancer (SCLC) with disease progression on or after platinum-based chemotherapy.

Biological Activity

Lurbinectedin (PM01183, PM-1183, LY-01017, Tryptamicidin, Zepsyre, ZEPZELCA), a DNA minor groove covalent binder with potent in vitro and in vivo anti-tumour activity. Lurbinectedin inhibits RMG1 and RMG2 cell growth with IC50 of 1.25 nM and 1.16 nM, respectively.

Mechanism of action

Lurbinectedin is a next-generation DNA minor groove binder that exerts potent antitumor activity in a low nanomolar range. Furthermore, it inhibits RNA-polymerase-II activity and promotes its specific degradation by the ubiquitin/proteasome machinery. In several human cancer cell lines, lurbinectedin blocks the transcription process through binding to CG-rich sequences near the promoters of protein-coding genes. This drug triggers both the degradation of phosphorylated RNA polymerase II (Pol II) on the DNA template and the generation of SSBs and DSBs that drive tumor cells to apoptosis. By attenuating the activity of the nucleotide excision repair (NER) mechanism, lurbinectedin was able to overcome cisplatin resistance in NER hyperactive cell lines. Lurbinectedin was also shown to inactivate Ewing Sarcoma Oncoprotein (EWS-FLI1) by nuclear redistribution leading to promotor inactivity and decreased mRNA and protein levels[1-2].

Side effects

The most common side effects include leukopenia, lymphopenia, fatigue, anemia, neutropenia, increased creatinine, increased alanine aminotransferase, increased glucose, thrombocytopenia, nausea, decreased appetite, musculoskeletal pain, decreased albumin, constipation, dyspnea, decreased sodium, increased aspartate aminotransferase, vomiting, cough, decreased magnesium and diarrhea.

Synthesis

Phenol 268 was subjected to oxidative dearomatization using phenylselenic anhydride. Subsequent esterification of the primary alcohol with (R)-N-Alloc-S-Fm-Cys (269) gave the hydroxy enone 270 in 72% overall yield for this two-step reaction. Macrocyclization followed the one-pot protocol reported by Corey to afford the sulfide 271 in 51% yield. Reduction to remove all allyl and Alloc protecting groups afforded the amine 272 in 85% yield. Amine 272 was reacted with 4-carboxaldehyde-1-methylpyridinium salt (273) to afford the oxalate 274 in 52% yield. Pictet-Spengler reaction with the tryptophan derivative 275 followed by iminium ion-mediated quenching of the cyano group by injection and hydrolysis afforded rubicin in 77% overall yield.

in vitro

Lurbinectedin exhibits significant antitumor activity toward chemosensitive and chemoresistant CCC cells in vitro. Lurbinectedin plus SN-38 combination has strong synergistic effects on both the cisplatin-resistant and paclitaxel-resistant CCC cell lines.

in vivo

An examination of mouse CCC cell xenografts reveals that lurbinectedin significantly inhibits tumor growth. Lurbinectedin plus SN-38 combination results in a significant synergistic effect. Everolimus significantly enhances the antitumor activity of lurbinectedin-based chemotherapies.

Mode of action

Lurbinectedin is an Alkylating Drug. The mechanism of action of lurbinectedin is as an Alkylating Activity.

References

[1] Kauffmann-Guerrero D, et al. Orphan Drugs in Development for the Treatment of Small-Cell Lung Cancer: Emerging Data on Lurbinectedin. Lung Cancer: Targets and Therapy, 2020; 11: 27–31.
[2] Gadducci A, et al. Trabectedin and lurbinectedin: Mechanisms of action, clinical impact, and future perspectives in uterine and soft tissue sarcoma, ovarian carcinoma, and endometrial carcinoma. Frontiers in Oncology, 2022; 12: 914342.

Lurbinectedin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Lurbinectedin manufacturers

Hebei Yanxi Chemical Co., Ltd.

Product: Lurbinectedin 497871-47-3
Price: US $30.00-1.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-11-24

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.

Product: Lurbinectedin 497871-47-3
Price: US $0.00/g
Min. Order: 1g
Purity: More Than 99%
Supply Ability: 100kg/Month
Release date: 2024-10-14

Henan Fengda Chemical Co., Ltd

Product: Lurbinectedin 497871-47-3
Price: US $6.00-1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-03-28

497871-47-3, LurbinectedinRelated Search:

Lurbinectedin (PM01183)

LURBINECTEDIN

PM 01183

PM01183

PM-01183

PM01183;PM-01183;PM 01183

Lurbinectidine

Spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'-[1H]pyrido[3,4-b]indol]-19-one, 5-(acetyloxy)-2',3',4',6,6a,7,9',13,14,16-decahydro-8,14-dihydroxy-6',9-dimethoxy-4,10,23-trimethyl-, (1'R,6R,6aR,7R,13S,14S,16R)- (9CI)

UNII-2CN60TN6ZS

Lurbinectedin,DNA/RNA Synthesis,inhibit,DNA Alkylator/Crosslinker,PM-01183,Inhibitor,PM 01183

Rubitidine

Cypermethrin Impurity 18 (Phenothrin)

Lurbinectedin Impurity

Lubic alternative

Rupee substitution

D3-Lurbinectedin

497871-47-3

C41H44N4O10S