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Details

Stereochemistry ACHIRAL
Molecular Formula C6H14ClN3O5S2
Molecular Weight 307.775
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAROMUSTINE

SMILES

CNC(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O

InChI

InChIKey=PVCULFYROUOVGJ-UHFFFAOYSA-N
InChI=1S/C6H14ClN3O5S2/c1-8-6(11)10(17(3,14)15)9(5-4-7)16(2,12)13/h4-5H2,1-3H3,(H,8,11)

HIDE SMILES / InChI
Molecular Formula C6H14ClN3O5S2
Molecular Weight 307.775
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Toxicological evaluation of 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-(methylaminocarbonyl)hydrazine (VNP40101M), a novel alkylating agent with potential antitumor activity, with intravenous administration in rats and dogs.
2002 Jan-Feb
Differential inhibition of cellular glutathione reductase activity by isocyanates generated from the antitumor prodrugs Cloretazine and BCNU.
2005 May 15
A phase II study of cloretazine (VNP40101M), a novel sulfonylhydrazine alkylating agent, in patients with very high risk relapsed acute myeloid leukemia.
2006 Dec
Activity of VNP40101M (Cloretazine) in the treatment of CNS tumor xenografts in athymic mice.
2007 Jul
Anti-tumor efficacy of Cloretazine (VNP40101M) alone and in combination with fludarabine in murine tumor and human xenograft tumor models.
2007 Jun
Advances in the management of AML in the elderly.
2007 Mar
Phase I trial of VNP40101M (Cloretazine) in children with recurrent brain tumors: a pediatric brain tumor consortium study.
2008 Feb 15
Acute myeloid leukemia in the elderly: conventional and novel treatment approaches.
2008 Jul
Gateways to clinical trials.
2008 May
Lethality to leukemia cell lines of DNA interstrand cross-links generated by Cloretazine derived alkylating species.
2008 Oct
Gateways to clinical trials.
2009 Apr
Gateways to clinical trials.
2009 May
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
Novel therapies for myelodysplastic syndromes.
2010 Apr
Phase I study of temozolomide and laromustine (VNP40101M) in patients with relapsed or refractory leukemia.
2010 Jun
Patents

Patents

05256820
2
05637619
2
08026395
3
20040121940
2
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:49:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:23 GMT 2023
Record UNII
14J2G0U3NQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAROMUSTINE
DASH   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
CLORETAZINE
Brand Name English
ONRIGIN
Brand Name English
LAROMUSTINE [MART.]
Common Name English
NSC-734246
Code English
VNP40101M
Code English
laromustine [INN]
Common Name English
Laromustine [WHO-DD]
Common Name English
VNP-40101M
Code English
LAROMUSTIN
Common Name English
LAROMUSTINE [USAN]
Common Name English
LAROMUSTINE [MI]
Common Name English
2-(2-CHLOROETHYL)-N-METHYL-1,2-BIS(METHYLSULFONYL)HYDRAZINECARBOXAMIDE
Systematic Name English
1,2-BIS(METHYLSULFONYL)-1-(2-CHLOROETHYL)-2-((METHYLAMINO)CARBONYL)HYDRAZINE
Systematic Name English
101M
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 424014
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
FDA ORPHAN DRUG 194104
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
EU-Orphan Drug EU/3/05/332
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
NCI_THESAURUS C1590
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
NCI_THESAURUS C2134
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
Code System Code Type Description
INN
8936
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
CAS
173424-77-6
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
SMS_ID
100000124522
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
MESH
C483604
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
EVMPD
SUB32202
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
FDA UNII
14J2G0U3NQ
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
NCI_THESAURUS
C2653
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
MERCK INDEX
m6695
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB05817
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
PUBCHEM
3081349
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
USAN
SS-85
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID30169614
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
NSC
734246
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL167691
Created by admin on Fri Dec 15 15:49:23 GMT 2023 , Edited by admin on Fri Dec 15 15:49:23 GMT 2023
PRIMARY
Related Record Type Details
Structure of S-(N-METHYLCARBAMOYL)GLUTATHIONE
METABOLITE -> PARENT
Structure of S-(N-METHYLCARBAMOYL)-L-CYSTEINE
METABOLITE -> PARENT
Structure of N-ACETYL-S-(2-(METHYLSULFONYL)ETHYL)-L-CYSTEINE
METABOLITE -> PARENT
Structure of N-ACETYL-S-(2-(2-(METHYLSULFONYL)HYDRAZINYLIDENE)ETHYL)-L-CYSTEINE
METABOLITE -> PARENT
Structure of VNP-4090CE
METABOLITE ACTIVE -> PRODRUG
Structure of L-.GAMMA.-GLUTAMYL-S-(2-(2-(METHYLSULFONYL)HYDRAZINYLIDENE)ETHYL)-L-CYSTEINYL-GLYCINE
METABOLITE -> PARENT
Structure of S-(2-(METHYLSULFONYL)ETHYL)GLUTATHIONE
METABOLITE -> PARENT
IN-VITRO
Structure of S-(2-(METHYLSULFONYL)ETHYL)-L-CYSTEINE
METABOLITE -> PARENT
Structure of N-ACETYL-S-((METHYLAMINO)CARBONYL)-L-CYSTEINE
METABOLITE -> PARENT
Related Record Type Details
Structure of VNP-4090CE
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