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

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

Molecular Formula	C18H16N2O
Molecular Weight	276.3324
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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	Binding Agent 1,076
DNA topoisomerase II 66	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 432	Primary		Approved 8,583	CELIPTIUM

C_max

Value	Dose	Analyte	Population
1.6 μg × eq/mL	100 mg/m² single, intravenous	ELLIPTINIUM plasma	Homo sapiens
936 ng/mL	94.9 mg/m² single, intravenous	ELLIPTINIUM plasma	Homo sapiens
1633 ng/mL	98.2 mg/m² single, intravenous	ELLIPTINIUM plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
3.33 μg × h/mL	94.9 mg/m² single, intravenous		ELLIPTINIUM plasma	Homo sapiens
2.5 μg × h/mL	98.2 mg/m² single, intravenous		ELLIPTINIUM plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
23.9 h	94.9 mg/m² single, intravenous		ELLIPTINIUM plasma	Homo sapiens
14.3 h	98.2 mg/m² single, intravenous		ELLIPTINIUM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
22%	94.9 mg/m² single, intravenous		ELLIPTINIUM plasma	Homo sapiens
22%	98.2 mg/m² single, intravenous		ELLIPTINIUM plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
80 mg/m2 3.01 times / week steady, intravenous Studied dose	unhealthy, ADULT	Other AEs: Xerostomia, Fatigue...
100 mg/m2 1 times / week steady, Studied dose	unhealthy	Other AEs: Hemolysis, Renal toxicity...

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AEs

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AE	Significance	Dose	Population
Anorexia	1 pts moderate, 3 pts severe, 5%	80 mg/m2 3.01 times / week steady, intravenous Studied dose	unhealthy, ADULT
Vomiting	2 pts moderate, 1 pts severe, 4%	80 mg/m2 3.01 times / week steady, intravenous Studied dose	unhealthy, ADULT
Fatigue	2 pts moderate, 5 pts severe, 8%	80 mg/m2 3.01 times / week steady, intravenous Studied dose	unhealthy, ADULT
Xerostomia	5pts moderate, 3 pts severe, 1%	80 mg/m2 3.01 times / week steady, intravenous Studied dose	unhealthy, ADULT
Drug fever	moderate, 1%	80 mg/m2 3.01 times / week steady, intravenous Studied dose	unhealthy, ADULT

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252		substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2,633	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1,388	substrate 4,014	likely

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PubMed

PubMed

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Title	Date	PubMed
Virostatic in vivo effect of elliptinium on Friend's retrovirus (a model for HIV infection).	1990	1369686
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991 Nov-Dec	1818183
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

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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

Substance Class	Chemical
Record UNII	H9B41234P4
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Classification Tree

Code System

Code

Antineoplastic Agent

NCI_THESAURUS

C1968

DNA Binding Agent

NCI_THESAURUS

C582

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Code System

Code

Type

Description

INN

4783

PRIMARY

NCI_THESAURUS

C1367

PRIMARY

ECHA (EC/EINECS)

261-216-0

PRIMARY

MESH

C027767

PRIMARY

EPA CompTox

DTXSID10207068

PRIMARY

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Related Record

Type

Details


					1F1959S062

ELLIPTINIUM

PARENT -> SALT/SOLVATE

Amount:

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Related Record

Type

Details


					1F1959S062

ELLIPTINIUM

ACTIVE MOIETY

Amount:

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.ncbi.nlm.nih.gov/pubmed/7003658">https://www.ncbi.nlm.nih.gov/pubmed/7003658</a></span></span></div></div>

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

Description

C_max

T_1/2

F_unbound

Drug as perpetrator