SOBUZOXANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H34N4O10
Molecular Weight	514.5262
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)COC(=O)OCN1C(=O)CN(CCN2CC(=O)N(COC(=O)OCC(C)C)C(=O)C2)CC1=O

InChI

InChIKey=OCOKWVBYZHBHLU-UHFFFAOYSA-N

InChI=1S/C22H34N4O10/c1-15(2)11-33-21(31)35-13-25-17(27)7-23(8-18(25)28)5-6-24-9-19(29)26(20(30)10-24)14-36-22(32)34-12-16(3)4/h15-16H,5-14H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C22H34N4O10
Molecular Weight	514.5262
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9685054
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/10632373 http://www.ncbi.nlm.nih.gov/pubmed/8384067 http://www.anticancer-drug.net/plant_alkaloids/sobuzoxane.htm

Sobuzoxane (MST-16), a dioxopiperazine, chelates metal cations and reduces the generation of free radicals due to metal-anthracycline complexes. It interacts with topoisomerase II and blocks the formation of topoisomerase II-DNA complex. Sobuzoxane effectively blocks cell proliferation and blocks cells in G2/M phase in selected human tumor cell lines. It protects cardiomyocytes from the cardiotoxicity induced by prolonged doxorubicin treatment. It’s indicated for treatment malignant lymphoma, is also used in adult T-cell leukemia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1654204	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malignant lymphoma 10 Sources: http://www.anticancer-drug.net/plant_alkaloids/sobuzoxane.htm	Primary		Approved 8583	Perazorin Approved Use malignant lymphoma, is also used in adult T-cell leukemia.
T-cell leukemia 1 Sources: http://www.anticancer-drug.net/plant_alkaloids/sobuzoxane.htm	Primary		Approved 8583	Perazorin Approved Use malignant lymphoma, is also used in adult T-cell leukemia.

C_max

Value	Dose	Analyte	Population
2.7 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	600 mg/m² single, oral dose: 600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.47 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	750 mg/m² single, oral dose: 750 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
7.42 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1500 mg/m² single, oral dose: 1500 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.15 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	200 mg/m² 1 times / day multiple, oral dose: 200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.93 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	270 mg/m² 1 times / day multiple, oral dose: 270 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.38 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	560 mg/m² 1 times / day multiple, oral dose: 560 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6.16 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	800 mg/m² 1 times / day multiple, oral dose: 800 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
11.46 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1000 mg/m² 1 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.41 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1200 mg/m² 1 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
20.59 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	600 mg/m² single, oral dose: 600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
35.46 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	750 mg/m² single, oral dose: 750 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
61.85 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1500 mg/m² single, oral dose: 1500 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
9.37 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	200 mg/m² 1 times / day multiple, oral dose: 200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.31 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	270 mg/m² 1 times / day multiple, oral dose: 270 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6.84 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	320 mg/m² 1 times / day multiple, oral dose: 320 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
66.04 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	560 mg/m² 1 times / day multiple, oral dose: 560 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
51.64 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	800 mg/m² 1 times / day multiple, oral dose: 800 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
74 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1000 mg/m² 1 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
62.81 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1200 mg/m² 1 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4.58 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	600 mg/m² single, oral dose: 600 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
5.28 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	750 mg/m² single, oral dose: 750 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.99 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1500 mg/m² single, oral dose: 1500 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.99 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	200 mg/m² 1 times / day multiple, oral dose: 200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.6 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	270 mg/m² 1 times / day multiple, oral dose: 270 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
7.56 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	560 mg/m² 1 times / day multiple, oral dose: 560 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.15 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	800 mg/m² 1 times / day multiple, oral dose: 800 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.64 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1000 mg/m² 1 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.47 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=24	1200 mg/m² 1 times / day multiple, oral dose: 1200 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)ETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
98% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/380101_4291004C1030_1_A01_1F.pdf#page=25			SOBUZOXANE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
1400 mg 2 times / day multiple, oral Highest studied dose Dose: 1400 mg, 2 times / day Route: oral Route: multiple Dose: 1400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8384067/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8384067/	Sources: https://pubmed.ncbi.nlm.nih.gov/8384067/
800 mg/m2 2 times / day multiple, oral RP2D Dose: 800 mg/m2, 2 times / day Route: oral Route: multiple Dose: 800 mg/m2, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/	Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/
800 mg/m2 1 times / day multiple, oral Studied dose Dose: 800 mg/m2, 1 times / day Route: oral Route: multiple Dose: 800 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/	Disc. AE: Leukopenia... AEs leading to discontinuation/dose reduction: Leukopenia (grade 3, 100%) Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/

AEs

AE	Significance	Dose	Population
Leukopenia	grade 3, 100% Disc. AE	800 mg/m2 1 times / day multiple, oral Studied dose Dose: 800 mg/m2, 1 times / day Route: oral Route: multiple Dose: 800 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2369134/

PubMed

Title	Date	PubMed
Medicinal chemistry of probimane and MST-16: comparison of anticancer effects between bisdioxopiperazines.	2006-07	16848748
MST-16, a novel derivative of bis(2,6-dioxopiperazine), synergistically enhances the antitumor effects of anthracyclines.	1998	9685054

Patents

Sample Use Guides

In Vivo Use Guide

1600 mg/m2 a day for 5-7 days at intervals of 2-3 weeks

Route of Administration: Oral

In Vitro Use Guide

IC50 against HeLa cell line of MST-16 (SOBUZOXANE) was 26.4 uM. MST-16 affecting chromosome segregation and leading also to cell G2/ M phase arrests, which finally reduces cell division rates

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:36 GMT 2025`
Record UNII	R1308VH37P
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SOBUZOXANE

Official Name

English

SOBUZOXANE [JAN]

Preferred Name

English

SOBUZOXANE [MART.]

Common Name

English

sobuzoxane [INN]

Common Name

English

SOBUZOXANE [MI]

Common Name

English

Sobuzoxane [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1968