Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H11ClN2O4S2 |
| Molecular Weight | 250.724 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(=O)(=O)NN(CCCl)S(C)(=O)=O
InChI
InChIKey=QVKFHBWVOPWLGX-UHFFFAOYSA-N
InChI=1S/C4H11ClN2O4S2/c1-12(8,9)6-7(4-3-5)13(2,10)11/h6H,3-4H2,1-2H3
LAROMUSTINE is a sulfonylhydrazine alkylating agent. It is metabolized to yield a chloroethylating compound (VNP-4090-CE) and a carbamoylating compound (methyl isocyanate). The former is primarily responsible for the antineoplastic effect of LAROMUSTINE. It alkylates the O6 position of guanine, resulting in DNA crosslinking, strand breaks, chromosomal aberrations, and disruption of DNA synthesis. The carbamoylating species contribute to antitumor activity by inhibiting O6-alkylguanine transferase, an enzyme involved with DNA repair. It was studied in the treatment of several types of cancer, however, its development was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential inhibition of cellular glutathione reductase activity by isocyanates generated from the antitumor prodrugs Cloretazine and BCNU. | 2005 May 15 |
|
| Role of O6-alkylguanine-DNA alkyltransferase in the cytotoxic activity of cloretazine. | 2005 Nov |
|
| Phase II study of Cloretazine for the treatment of adults with recurrent glioblastoma multiforme. | 2007 Jan |
|
| Nitric oxide donors attenuate clongenic potential in rat C6 glioma cells treated with alkylating chemotherapeutic agents. | 2007 May 11 |
|
| Gateways to clinical trials. | 2008 May |
|
| Clinical activity of laromustine (Onrigin™) in hematologic malignancies. | 2009 Oct |
|
| An in vitro evaluation of the victim and perpetrator potential of the anticancer agent laromustine (VNP40101M), based on reaction phenotyping and inhibition and induction of cytochrome P450 enzymes. | 2009 Sep |
Patents
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
6ZE344986H
Created by
admin on Sat Dec 16 09:41:43 GMT 2023 , Edited by admin on Sat Dec 16 09:41:43 GMT 2023
|
PRIMARY | |||
|
m6695
Created by
admin on Sat Dec 16 09:41:43 GMT 2023 , Edited by admin on Sat Dec 16 09:41:43 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID70436695
Created by
admin on Sat Dec 16 09:41:43 GMT 2023 , Edited by admin on Sat Dec 16 09:41:43 GMT 2023
|
PRIMARY | |||
|
127792-84-1
Created by
admin on Sat Dec 16 09:41:43 GMT 2023 , Edited by admin on Sat Dec 16 09:41:43 GMT 2023
|
PRIMARY | |||
|
10198873
Created by
admin on Sat Dec 16 09:41:43 GMT 2023 , Edited by admin on Sat Dec 16 09:41:43 GMT 2023
|
PRIMARY |
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
PRODRUG (METABOLITE ACTIVE)
SUBSTANCE RECORD
