PIPOSULFAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H22N2O8S2
Molecular Weight	386.442
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(=O)(=O)OCCC(=O)N1CCN(CC1)C(=O)CCOS(C)(=O)=O

InChI

InChIKey=NUKCGLDCWQXYOQ-UHFFFAOYSA-N

InChI=1S/C12H22N2O8S2/c1-23(17,18)21-9-3-11(15)13-5-7-14(8-6-13)12(16)4-10-22-24(2,19)20/h3-10H2,1-2H3

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5338383 | https://www.ncbi.nlm.nih.gov/pubmed/5556760 | https://www.drugfuture.com/chemdata/piposulfan.html

Piponulfan is neutral, difunctional alkylating derivative of piperazine. This agent was studied for their antineoplastic activity. Piposulfan has been found to be active against the following mouse tumors: sarcoma 180, carcinoma 755, and leukemia 1210. In patients with polycythemia piposulfan produced a response rate similar to that seen with pipobroman, busulfan, and triethylene melamine. However, piposulfan produces noticeably less toxicity than standard recommended doses of either busulfan or triethylene melamine. Various degrees of therapeutie remissions were seen in patients with malignant lymphomas, acute and chronic leukemia, multiple myeloma, adenocarcinomas, epidermoid carcinomas, and various types of sarcomas. The most common adverse reactions to piposulfan involved the hematopoietic (bone marrow depression) and gastrointestinal organs.

Originator

Approval Year

PubMed

Title	Date	PubMed
Midwest cooperative group evaluation of piposulfan (A-20968) in cancer.	1967 May-Jun	5338383
The treatment of lepromatous leprosy and erythema nodosum leprosum with the cytostatic drugs Ancyte and Vercyte.	1967 Oct	6073259
[Effect of piposulfan (ancyte) in malignant lymphomas and solid tumors].	1968	4914032
Effect of piposulfan (NSC-47774) on malignant lymphomas and solid tumors.	1968 Apr	5244316
Treatment of chronic granulocytic leukemia with piposulfan (NSC-47774).	1969 Apr	5256921
Effects of piposulfan (Ancyte) on protein and DNA synthesis in Ehrlich ascites carcinoma.	1971 Jun 8	5556760
[Novel Bis-sulfonic Acid Esters with Cytostatic Activity (author's transl)].	1976	191037
Formulation and antitumor activity evaluation of nanocrystalline suspensions of poorly soluble anticancer drugs.	1996 Feb	8932448
Treatment of human prostate tumors PC-3 and TSU-PR1 with standard and investigational agents in SCID mice.	1997	9220288

Patents

Sample Use Guides

In Vivo Use Guide

Single dose - 200 mg/kg

Route of Administration: Intraperitoneal

Name

Type

Language

PIPOSULFAN

Official Name

English

A-20968

Code

English

ANCYTE

Brand Name

English

1,4-Dihydracryloylpiperazine dimethanesulfonate (ester)

Common Name

English

PIPERAZINE, 1,4-BIS(3-((METHYLSULFONYL)OXY)-1-OXOPROPYL)-

Systematic Name

English

PIPOSULFAN [MI]

Common Name

English

PIPOSULFAN [USAN]

Common Name

English

piposulfan [INN]

Common Name

English

1,4-DIHYDRACRYLOYLPIPERAZINE DIMETHANESULPHONATE (ESTER)

Common Name

English

NSC-47774

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C222