2-CHLOROETHYL-3-SARCOSINAMIDE-1-NITROSOUREA

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H11ClN4O3
Molecular Weight	222.63
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2-CHLOROETHYL-3-SARCOSINAMIDE-1-NITROSOUREA

Structure Search

SMILES

CN(CC(N)=O)C(=O)N(CCCl)N=O

InChI

InChIKey=HYHJFNXFVPGMBI-UHFFFAOYSA-N

InChI=1S/C6H11ClN4O3/c1-10(4-5(8)12)6(13)11(9-14)3-2-7/h2-4H2,1H3,(H2,8,12)

HIDE SMILES / InChI

Molecular Formula	C6H11ClN4O3
Molecular Weight	222.63
Charge	0
Count

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

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/sarcnu | https://www.ncbi.nlm.nih.gov/pubmed/11181897 | https://www.ncbi.nlm.nih.gov/pubmed/16034522 | https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=150601

2-chloroethyl-3-sarcosinamide-1-nitrosourea (SarCNU) is an alkylating chloroethylnitrosourea with antineoplastic activity. It is a selective cytotoxin that enters cells via the extraneuronal transporter for monoamine transmitters (EMT). Both in vitro and in vivo studies demonstrated that SarCNU was more effective than BCNU against human gliomas. Selectively accumulating in some tumor cells, SarCNU forms covalent linkages with nucleophilic centers in DNA, causing depurination, base pair miscoding, strand scission, and DNA-DNA cross-linking, which may result in cytotoxicity. SarCNU crosses the blood-brain-tumour-barrier and is taken orally. Phase II trial of SarCNU in malignant glioma revealed unexpected pulmonary toxicity. SarCNU was not FDA approved for orphan indication of malignant glioma.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Both extraneuronal monoamine transporter and O(6)-methylguanine-DNA methyltransferase expression influence the antitumor efficacy of 2-chloroethyl-3-sarcosinamide- 1-nitrosourea in human tumor xenografts.	2001 Mar	11181897
Phase II trial of SarCNU in malignant glioma: unexpected pulmonary toxicity with a novel nitrosourea: a phase II trial of the national cancer institute of canada clinical trials group.	2005 Dec	16034522
SarCNU in recurrent or metastatic colorectal cancer: a phase II study of the National Cancer Institute of Canada Clinical Trials Group.	2006 Jul	16502354

Patents

Sample Use Guides

In Vivo Use Guide

Eighteen patients with recurrent or metastatic colorectal cancer following first-line chemotherapy were treated with SarCNU 860 mg/m2 orally day 1, 5 and 9 every 6 weeks.

Route of Administration: Oral

In Vitro Use Guide

The in vitro myelotoxicity of SarCNU at 1-8 ug/ml was determined in bone marrow cells from normal volunteers in the CFU-C assay.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:51:54 GMT 2023` Edited by `admin` on `Sat Dec 16 05:51:54 GMT 2023`
Record UNII	BHB013S3MO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-CHLOROETHYL-3-SARCOSINAMIDE-1-NITROSOUREA

Common Name

English

2-Chloroethyl-3-sarcosinamide-1-nitrosourea [WHO-DD]

Common Name

English

SARMUSTINE

Brand Name

English

ACETAMIDE, 2-((((2-CHLOROETHYL)NITROSOAMINO)CARBONYL)METHYLAMINO)-

Systematic Name

English

SARCNU

Common Name

English

SARCOSINEAMIDE CHLOROETHYLNITROSOUREA

Systematic Name

English

NSC-364432

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C699