CYTOCHLOR

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H12ClN3O4
Molecular Weight	261.662
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=C1Cl)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

InChIKey=NGGRGTWYSXYVDK-RRKCRQDMSA-N

InChI=1S/C9H12ClN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB12383
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/record/NCT00521183 | https://www.ncbi.nlm.nih.gov/pubmed/2432451 | https://clinicaltrials.gov/ct2/show/record/NCT00077051 | https://www.ncbi.nlm.nih.gov/pubmed/14751833

Cytochlor is a radio-sensitizing pyrimidine nucleoside with potential antineoplastic activity. Cytochlor is metabolized first to a phosphate derivative, CldCMP, by the enzyme deoxycytidine kinase and then to the active uracyl derivative, CldUMP, by the enzyme dCMP deaminase. CldUMP, the active metabolite, incorporates into DNA and, upon exposure to radiation, induces the formation of uracil radicals and double-strand DNA breaks. Cytochlor has been used in trials studying the treatment of Head and Neck Cancer and Brain and Central Nervous System Tumors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://link.springer.com/chapter/10.1007/978-3-319-13278-5_15	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Brain and central nervous system tumors 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00521183	Primary		Phase I 438	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	DCK 1 cytidine deaminase 1

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
cytidine deaminase 1	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/6291452/	yes [Km 1.1 uM]
DCK 1	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/6291452/	yes [Km 56 uM]

Sourcing

Vendor/Aggregator	ID	URL
BioSynth	W-202328	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-202328
BOC Sciences	32387-56-7	http://www.bocsci.com/description.asp?cas=32387-56-7
eMolecules	29257240	https://orderbb.emolecules.com/search/#?query=29257240
mcule	MCULE-8189824669	https://mcule.com/MCULE-8189824669/
Norris Pharm	NSZB-A194536

PubMed

Title	Date	PubMed
Potent inhibition of HhaI DNA methylase by the aglycon of 2-(1H)-pyrimidinone riboside (zebularine) at the GCGC recognition domain.	2003-12	14751833

Patents

Sample Use Guides

In Vivo Use Guide

Patients receive cytochlor IV (50 mg/m2/day) and tetrahydrouridine (720 mg/m2/day) IV over 5 minutes on 3 days in week 1 and on days 1-5 in weeks 2 and 3.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

CYTOCHLOR

Common Name

English

NSC-371331

Preferred Name

English

5-CHLORODEOXYCYTIDINE

Systematic Name

English

5-CLDC

Common Name

English

CLDC

Common Name

English

5-CHLORO-2'-DEOXYCYTIDINE

Systematic Name

English

CYTIDINE, 5-CHLORO-2'-DEOXY-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C798