FLUROCITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H10FN3O4
Molecular Weight	243.1918
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=NC(=N)C(F)=C[N@]3[C@]1([H])O[C@H](CO)[C@H]2O

InChI

InChIKey=PAYBYKKERMGTSS-MNCSTQPFSA-N

InChI=1S/C9H10FN3O4/c10-3-1-13-8-6(5(15)4(2-14)16-8)17-9(13)12-7(3)11/h1,4-6,8,11,14-15H,2H2/t4-,5-,6+,8-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1149046
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/348088

Flurocitabine is an anti-metabolite that was developed by Hoffmann-La Roche for the treatment of cancer. The drug is metabolized to 2 biologically active substances, AFC (1-beta-D-arabinofuranosyl-5-fluorocytosine) and AFU (arabinofuranosyl-5-fluorouracil). Flurocitabine was tested against stomach cancer, pancreatic cancer, small cell lung cancer and AML, however, the development was terminated in the early phases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA polymerase 2 Target ID: DNA polymerase Sources: http://link.springer.com/chapter/10.1007%2F978-1-4613-4352-3_67	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/93030	Primary	Phase II 1132	Unknown Approved Use Unknown
Pancreatic cancer 97 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6159121	Primary	Phase II 1132	Unknown Approved Use Unknown
Acute non-lymphocytic leukemia 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6170414	Primary	Phase I 428	Unknown Approved Use Unknown
Small-cell lung cancer 41 Sources: http://ascopubs.org/doi/pdf/10.1200/jco.1992.10.3.484	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
BOC Sciences	37717-21-8	http://www.bocsci.com/description.asp?cas=37717-21-8
Compound Cloud	3034016
eMolecules	110015564	https://orderbb.emolecules.com/search/#?query=110015564

PubMed

Title	Date	PubMed
Physiological disposition of 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine in humans.	1975 Sep	1149046
Comparative ultrastructure of submaxillary salivary glands from mice treated with cytosine arabinoside, cyclocytidine, and anhydro-ara-5-fluorocytidine.	1976 Jul	64296
Phase I study of weekly administration of anhydroara-5-fluorocytidine (NSC-166641).	1976 Mar	1260783
Phase II study of anhydro-ara-5-fluorocytidine in adenocarcinoma of gastrointestinal tract, epidermoid carcinoma of lung, head and neck, breast carcinoma and small cell anaplastic carcinoma of lung. A study report of the E.O.R.T.C. early clinical trial cooperative group.	1978 Feb	75105
Phase I and II clinical study of anhydro-ara-5-fluorocytosine (AAFC) and ICRF-159 combination in adenocarcinoma of digestive origin.	1978 Winter	93030
Anhydro-ara-5-fluorocytidine (AAFC) in gastrointestinal cancer. A phase II study.	1980	6159121

Patents

Sample Use Guides

In Vivo Use Guide

The maximum tolerated dose is 650 mg/m2 I.V. weekly (stomach cancer). In acute nonlymphocytic leukemia the dose is 800 mg/m2 (600mg/m2 in children) given every 12 hours until marrow hypocellularity is achieved. In Small-Cell Lung Cancer the dose is 15-20 mg/m2 IV given daily for 5 days every 3 weeks or 33-40 mg/m2 IV given weekly.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

FLUROCITABINE

Official Name

English

(2R,3R,3AS,9AR)-7-FLUORO-2,3,3A,9A-TETRAHYDRO-3-HYDROXY-6-IMINO-6H-FURO(2',3':4,5)OXAZOLO(3,2-A)PYRIMIDINE-2-METHANOL

Common Name

English

CYCLO FC

Common Name

English

6H-FURO(2',3';4,5)OXAZOLO(3,2-A)PYRIMIDINE-2-METHANOL, 7-FLUORO-2,3,3A,9A-TETRAHYDRO-3-HYDROXY-6-IMINO-, (2R-(2.ALPHA.,3.BETA.,3A.BETA.,9A.BETA.))-

Common Name

English

5-FLUOROCYCLOCYTIDINE

Common Name

English

AAFC

Common Name

English

FLUROCITABINE [USAN]

Common Name

English

flurocitabine [INN]

Common Name

English

RO-210702

Code

English

6H-FURO(2',3':4,5)OXAZOLO(3,2-A)PYRIMIDINE-2-METHANOL, 7-FLUORO-2,3,3A,9A-TETRAHYDRO-3-HYDROXY-6-IMINO-, (2R,3R,3AS,9AR)-

Systematic Name

English

2,2'-ANHYDRO-5-FLUORO-1-.BETA.-D-ARABINOFURANOSYLCYTOSINE

Common Name

English

ANHYDRO-ARABINOSYL-5-FLUORO-CYTOSINE

Common Name

English

5'-FLUOROCYCLOCYTIDINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557