ELLIPTINIUM ACETATE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H17N2O.C2H3O2
Molecular Weight	336.3844
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC([O-])=O.CC1=C2C=C[N+](C)=CC2=C(C)C3=C1NC4=C3C=C(O)C=C4

InChI

InChIKey=BOMZMNZEXMAQQW-UHFFFAOYSA-N

InChI=1S/C18H16N2O.C2H4O2/c1-10-15-9-20(3)7-6-13(15)11(2)18-17(10)14-8-12(21)4-5-16(14)19-18;1-2(3)4/h4-9,21H,1-3H3;1H3,(H,3,4)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7003658

Elliptinium is an antineoplastic agent, which was used in the treatment of metastatic breast cancer in France under the name Celiptium. The drug is known to intercalate into DNA and inhibit topoisomerase II. Several studies have demonstrated that this molecule can be oxidized, yielding a reactive electrophilic form, which is able to bind covalently to a nucleophilic biological molecule.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7003658	Binding Agent 1076
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: DOI 10.1007/978-1-4684-5242-6_17, Chandra P., 'New Experimental Modalities in the Control of Neoplasia' (2012), p. 236, Retrieved from https://books.google.com/books?id=5JPuBwAAQBAJ&dq	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8484977	Primary		Approved 8583	CELIPTIUM Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1.6 μg × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3196392/	100 mg/m² single, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
936 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	94.9 mg/m² single, intravenous dose: 94.9 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
1633 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	98.2 mg/m² single, intravenous dose: 98.2 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3.33 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	94.9 mg/m² single, intravenous dose: 94.9 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	98.2 mg/m² single, intravenous dose: 98.2 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
23.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	94.9 mg/m² single, intravenous dose: 94.9 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
14.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	98.2 mg/m² single, intravenous dose: 98.2 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
22% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	94.9 mg/m² single, intravenous dose: 94.9 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
22% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6891926/	98.2 mg/m² single, intravenous dose: 98.2 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		ELLIPTINIUM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	Other AEs: Xerostomia, Fatigue... Other AEs: Xerostomia (5pts moderate, 3 pts severe, 1%) Fatigue (2 pts moderate, 5 pts severe, 8%) Anorexia (1 pts moderate, 3 pts severe, 5%) Vomiting (2 pts moderate, 1 pts severe, 4%) Muscular cramps (severe, 4%) Phlebitis (moderate, 1%) Drug fever (moderate, 1%) Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
100 mg/m2 1 times / week steady, Studied dose Dose: 100 mg/m2, 1 times / week Route: steady Dose: 100 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/	unhealthy Health Status: unhealthy Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/	Other AEs: Hemolysis, Renal toxicity... Other AEs: Hemolysis (5 patients) Renal toxicity (Grade 2, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/

AEs

AE	Significance	Dose	Population
Anorexia	1 pts moderate, 3 pts severe, 5%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Vomiting	2 pts moderate, 1 pts severe, 4%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Fatigue	2 pts moderate, 5 pts severe, 8%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Xerostomia	5pts moderate, 3 pts severe, 1%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Drug fever	moderate, 1%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Phlebitis	moderate, 1%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Muscular cramps	severe, 4%	80 mg/m2 3.01 times / week steady, intravenous Studied dose Dose: 80 mg/m2, 3.01 times / week Route: intravenous Route: steady Dose: 80 mg/m2, 3.01 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8484977/
Hemolysis	5 patients	100 mg/m2 1 times / week steady, Studied dose Dose: 100 mg/m2, 1 times / week Route: steady Dose: 100 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/	unhealthy Health Status: unhealthy Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/
Renal toxicity	Grade 2, 1 patient	100 mg/m2 1 times / week steady, Studied dose Dose: 100 mg/m2, 1 times / week Route: steady Dose: 100 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/	unhealthy Health Status: unhealthy Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4016774/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252		substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8221648/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/34486940/	likely

PubMed

Title	Date	PubMed
Virostatic in vivo effect of elliptinium on Friend's retrovirus (a model for HIV infection).	1990	1369686
Assessment of candidate anticryptosporidial agents in an immunosuppressed rat model.	1993 Mar	8440946
Inhibitors of human immunodeficiency virus integrase.	1993 Mar 15	8460151
Viral and immunologic follow up of 4 to 9 years of AIDS treatments by quadruple combinations of virostatics including integrase inhibitors applied in short sequences differing by drug rotation.	2002 Jan	11860730
Anticancer drugs from marine flora: an overview.	2010	21461373
Immunotargeting of collagenase on thrombus.	2010 Nov 16	21187949

Sample Use Guides

In Vivo Use Guide

In a clinical study, elliptinium (acetate salt) was given at a dose of 80 mg/m2 daily for 3 consecutive days every 21 days.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

ELLIPTINIUM ACETATE

Official Name

English

CELIPTIUM

Preferred Name

English

ELLIPTINIUM ACETATE [MI]

Common Name

English

HME

Common Name

English

elliptinium acetate [INN]

Common Name

English

9-HYDROXY-2,5,11-TRIMETHYL-6H-PYRIDO(4,3-B)CARBAZOLIUM ACETATE

Systematic Name

English

NSC-264137

Code

English

Elliptinium acetate [WHO-DD]

Common Name

English

9-HYDROXY-2,5,11-TRIMETHYL-6H-PYRIDO(4,3-B)CARBAZOLIUM ACETATE (1:1)

Systematic Name

English

ELLIPTINIUM ACETATE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1968