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Lurbinectedin

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ACTIVE PHARMA INGREDIENTS

12 API Suppliers, 7 USDMF, 4 NDC API, 7 Listed Suppliers

12 API Suppliers
7 USDMF
4 NDC API
7 Listed Suppliers

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26 Drugs in Development

26 Drugs in Development

FINISHED DOSAGE FORMULATIONS

4 FDF Dossiers, 1 FDA Orange Book, 1 Europe, 1 Canada, 1 Listed Dossiers

4 FDF Dossiers
1 FDA Orange Book
1 Europe
1 Canada
1 Listed Dossiers

DIGITAL CONTENT

3 DATA COMPILATION #PharmaFlow, 32 NEWS #PharmaBuzz

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3 DATA COMPILATION #PharmaFlow
32 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions, 1 Finished Drug Prices, 4 Annual Reports

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1 US Medicaid Prescriptions
1 Finished Drug Prices
4 Annual Reports

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2 APIs

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2 APIs

PATENTS & EXCLUSIVITIES

1 US Patents, 2 US Exclusivities

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1 US Patents
2 US Exclusivities

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 0

MARKET PLACE

API

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

26DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

1,637,629

Annual Reports (USD Million)

897

Finished Drug Prices

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Chemistry

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Also known as: 497871-47-3, Pm01183, Tryptamicidin, Zepzelca, Pm-01183, Pm-1183

Molecular Formula

C₄₁H₄₄N₄O₁₀S

Molecular Weight

784.9 g/mol

InChI Key

YDDMIZRDDREKEP-HWTBNCOESA-N

FDA UNII

2CN60TN6ZS

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

1 2D Structure

Lurbinectedin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R,2R,3R,11S,12S,14R,26R)-5,12-dihydroxy-6,6'-dimethoxy-7,21,30-trimethyl-27-oxospiro[17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaene-26,1'-2,3,4,9-tetrahydropyrido[3,4-b]indole]-22-yl] acetate

2.1.2 InChI

InChI=1S/C41H44N4O10S/c1-17-11-20-12-25-39(48)45-26-14-52-40(49)41(38-22(9-10-42-41)23-13-21(50-5)7-8-24(23)43-38)15-56-37(31(45)30(44(25)4)27(20)32(47)33(17)51-6)29-28(26)36-35(53-16-54-36)18(2)34(29)55-19(3)46/h7-8,11,13,25-26,30-31,37,39,42-43,47-48H,9-10,12,14-16H2,1-6H3/t25-,26-,30+,31+,37+,39-,41+/m0/s1

2.1.3 InChI Key

YDDMIZRDDREKEP-HWTBNCOESA-N

2.1.4 Canonical SMILES

CC1=CC2=C(C3C4C5C6=C(C(=C7C(=C6C(N4C(C(C2)N3C)O)COC(=O)C8(CS5)C9=C(CCN8)C2=C(N9)C=CC(=C2)OC)OCO7)C)OC(=O)C)C(=C1OC)O

2.1.5 Isomeric SMILES

CC1=CC2=C([C@@H]3[C@@H]4[C@H]5C6=C(C(=C7C(=C6[C@@H](N4[C@H]([C@H](C2)N3C)O)COC(=O)[C@@]8(CS5)C9=C(CCN8)C2=C(N9)C=CC(=C2)OC)OCO7)C)OC(=O)C)C(=C1OC)O

2.2 Other Identifiers

2.2.1 UNII

2CN60TN6ZS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Pm 01183

2. Pm-01183

3. Pm01183

2.3.2 Depositor-Supplied Synonyms

1. 497871-47-3

2. Pm01183

3. Tryptamicidin

4. Zepzelca

5. Pm-01183

6. Pm-1183

7. 2cn60tn6zs

8. Pm 01183

9. Pm1183

10. [(1r,2r,3r,11s,12s,14r,26r)-5,12-dihydroxy-6,6'-dimethoxy-7,21,30-trimethyl-27-oxospiro[17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaene-26,1'-2,3,4,9-tetrahydropyrido[3,4-b]indole]-22-yl] Acetate

11. Zepsyre

12. Lurbinectedin [inn]

13. Unii-2cn60tn6zs

14. Lurbinectedin [mi]

15. Lurbinectedin [usan:inn]

16. Lurbinectedin [usan]

17. Lurbinectedin [who-dd]

18. Chembl4297516

19. Schembl16152477

20. Gtpl10681

21. Dtxsid30198065

22. Lurbinectedin [orange Book]

23. Ex-a4316

24. Who 9397

25. Nsc826275

26. S9603

27. At22223

28. Cs-6323

29. Db12674

30. Nsc-826275

31. Hy-16293

32. J3.531.659k

33. J3.652.626b

34. Pm01183;pm-1183;ly-01017;ryptamicidin

35. Q27254568

36. (1'r,6r,6ar,7r,13s,14s,16r)-8,14-dihydroxy-6',9-dimethoxy-4,10,23-trimethyl-19-oxo-2',3',4',6,7,9',12,13,14,16-decahydro-6ahspiro(7,13-azano-6,16-(epithiopropanooxymethano)(1,3)dioxolo(7,8)isoquinolino(3,2-b)(3)benzazocine-20,1'-pyrido(3,4-b)indol)-5-yl Acetate

37. [(1r,2r,3r,11s,12s,14r,26r)-5,12-dihydroxy-6,6'-dimethoxy-7,21,30-trimethyl-27-oxospiro[17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaene-26,1'-2,3,4,9-tetrahydropyrido[3,4-b]indole]-22

38. 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)-

2.4 Create Date

2012-06-18

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₄₄N₄O₁₀S
Molecular Weight	784.9 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	4
Exact Mass	784.27781479 g/mol
Monoisotopic Mass	784.27781479 g/mol
Topological Polar Surface Area	190 Å²
Heavy Atom Count	56
Formal Charge	0
Complexity	1530
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

4 Drug and Medication Information

4.1 Drug Indication

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.

Treatment of small cell lung cancer

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lurbinectedin exerts its chemotherapeutic activity by covalently binding to DNA, resulting in double-strand DNA breaks and subsequent cell death. Lurbinectedin has been associated with myelosuppression, and patients receiving therapy with this agent should be closely monitored for evidence of cytopenias. Prior to beginning therapy, ensure baseline neutrophil counts are >1,500 cells/mm³ and platelet counts are >100,000/mm³. The supplementary use of granulocyte colony-stimulating factor (G-CSF) should be considered if the neutrophil count falls below 500 cells/mm³. Lurbinectedin has also been associated with hepatotoxicity. Monitor liver function tests at baseline and regular intervals throughout therapy, and consider holding, reducing, or permanently discontinuing therapy based on the severity of observed hepatotoxicity.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

LURBINECTEDIN

5.2.2 FDA UNII

2CN60TN6ZS

5.2.3 Pharmacological Classes

Alkylating Drug [EPC]; Alkylating Activity [MoA]

5.3 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XX - Other antineoplastic agents

L01XX69 - Lurbinectedin

5.4 Absorption, Distribution and Excretion

Absorption

Following intravenous administration, the C_max and AUC_0-inf were 107 g/L and 551 g*h/L, respectively. No accumulation between dosing intervals (every 3 weeks) has been observed. No significant differences in absorption were found between special populations (e.g. based on age, sex, ethnicity, etc.), but lurbinectedin has not been studied in the setting of severe renal impairment or moderate/severe hepatic impairment.

Route of Elimination

Approximately 89% of a given dose is recovered in the feces (<0.2% unchanged) and 6% in the urine (1% unchanged).

Volume of Distribution

The steady-state volume of distribution of lurbinectedin is 504 L.

Clearance

The total plasma clearance of lurbinectedin is approximately 11 L/h.

5.5 Metabolism/Metabolites

Lurbinectedin is metabolized primarily by CYP3A4 _in vitro_, though specific data regarding its biotransformation are lacking. An N-desmethylated metabolite has been identified in canine subjects.

5.6 Biological Half-Life

The terminal half-life of lurbinectedin is 51 hours.

5.7 Mechanism of Action

Lurbinectedin is a DNA alkylating agent. It covalently binds to guanine residues in the DNA minor groove, forming adducts that bend the DNA helix towards the major groove. This process triggers a cascade of events that affect the activity of transcription factors and impairs DNA repair pathways, ultimately leading to double-strand DNA breaks and eventual cell death. Additional mechanism(s) of action include inhibition of RNA-polymerase-II activity, inactivation of Ewing Sarcoma Oncoprotein (EWS-FL11) via nuclear redistribution, and the inhibition of human monocyte activity and macrophage infiltration into tumor tissue.

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