CARBOQUONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H19N3O5
Molecular Weight	321.3285
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(COC(N)=O)C1=C(N2CC2)C(=O)C(C)=C(N3CC3)C1=O

InChI

InChIKey=SHHKQEUPHAENFK-UHFFFAOYSA-N

InChI=1S/C15H19N3O5/c1-8-11(17-3-4-17)14(20)10(9(22-2)7-23-15(16)21)12(13(8)19)18-5-6-18/h9H,3-7H2,1-2H3,(H2,16,21)

HIDE SMILES / InChI

Molecular Formula	C15H19N3O5
Molecular Weight	321.3285
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3279914
Curator's Comment: Description was created based on several sources, including http://www.ndrugs.com/?s=carboquone

Carboquone (CQ) is an anticancer alkylating agent synthesized and developed by Arakawa et al. (Sankyo Co, Ltd.) in 1970, having chemical structure, 2,5-bis-(1-aziridinyl)-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl- 1,4- benzoquinone. The antitumor efficacies of CQ were reported as excellent, however, the side effects are considerably strong. Carboquone is used to treat various forms of cancer. It is indicated for the treatment of metastatic testicular tumors, metastatic ovarian tumors and advanced bladder cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell growth 21 Target ID: GO:0016049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9703365	Inhibitor 8504		0.009 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15179836	Palliative	Preclinical	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2924889	Primary	Preclinical	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8217372	Primary	Preclinical	Unknown Approved Use Unknown
Lung cancer 70 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10506642	Primary	Approved 8583	Carboquone Approved Use Lung cancer, malignant lymphoma, CML Launch Date 1974
Malignant lymphoma 10 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10506642	Primary	Approved 8583	Carboquone Approved Use Lung cancer, malignant lymphoma, CML Launch Date 1974
Chronic myelogenous leukemia 21 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10506642	Primary	Approved 8583	Carboquone Approved Use Lung cancer, malignant lymphoma, CML Launch Date 1974

Doses

Dose	Population	Adverse events
0.25 mg 2 times / day multiple, oral Studied dose Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: https://dlisv03.media.osaka-cu.ac.jp/contents/osakacu/journal/00306096-49-2-77.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://dlisv03.media.osaka-cu.ac.jp/contents/osakacu/journal/00306096-49-2-77.pdf	Other AEs: Leukocytopenia... Other AEs: Leukocytopenia Sources: https://dlisv03.media.osaka-cu.ac.jp/contents/osakacu/journal/00306096-49-2-77.pdf
1 mg 1 times / day multiple, oral Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf	Other AEs: Leukopenia, Thrombopenia... Other AEs: Leukopenia (16.7%) Thrombopenia (8.3%) Anorexia (8.3%) Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf

AEs

AE	Significance	Dose	Population
Leukocytopenia		0.25 mg 2 times / day multiple, oral Studied dose Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: https://dlisv03.media.osaka-cu.ac.jp/contents/osakacu/journal/00306096-49-2-77.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://dlisv03.media.osaka-cu.ac.jp/contents/osakacu/journal/00306096-49-2-77.pdf
Leukopenia	16.7%	1 mg 1 times / day multiple, oral Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf
Anorexia	8.3%	1 mg 1 times / day multiple, oral Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf
Thrombopenia	8.3%	1 mg 1 times / day multiple, oral Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.jstage.jst.go.jp/article/tjem1920/138/2/138_2_151/_pdf

PubMed

Title	Date	PubMed
Postoperative adjuvant use of carmofur for early breast cancer.	2003-12	15179836
Current status of oral anticancer drugs in Japan.	1999-10	10506642
Treatment of multiple myeloma with carboquone-prednisolone.	1989-03	2924889
Hypoxia enhances the lethality of mitomycin C and carboquone against human malignant tumor cells in vitro.	1989	2509206
[An anticancer drug--carboquone].	1988-03	3279914

Patents

Sample Use Guides

In Vivo Use Guide

Oral Chronic myeloid leukaemia Adult: Initial doses for remission induction: 1-2 mg daily. Maintenance: 0.25-0.75 mg every other day or twice wkly; adjust dose to maintain WBC count between 8000 and 15000/mm 3. Doses may vary depending on regimens. Oral Cancer chemotherapy Adult: 1-1.5 mg daily in 2-3 divided doses.

Route of Administration: Oral

In Vitro Use Guide

Treatment with 0.03 microM of CQ for 30 min inhibited the clonogenicity of HeLa cells by 41.5%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:26:48 GMT 2025` Edited by `admin` on `Mon Mar 31 18:26:48 GMT 2025`
Record UNII	1CB0HBT12C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBOQUONE

Official Name

English

ESQUINON

Preferred Name

English

CARBOQUONE [JAN]

Common Name

English

2,5-BIS(1-AZIRIDINYL)-3-(2-HYDROXY-1-METHOXYETHYL)-6-METHYL-P-BENZOQUINONE CARBAMATE (ESTER)

Common Name

English

carboquone [INN]

Common Name

English

CARBOQUONE [MI]

Common Name

English

CARBOQUONE [MART.]

Common Name

English

Carboquone [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

L01AC03