CYTARABINE OCFOSFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H49N3O8P.Na
Molecular Weight	597.6568
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCCCCCCCCCCCCCCCCCOP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N2C=CC(N)=NC2=O

InChI

InChIKey=JOJYUFGTMHSFEE-YONYXQDTSA-M

InChI=1S/C27H50N3O8P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-36-39(34,35)37-21-22-24(31)25(32)26(38-22)30-19-18-23(28)29-27(30)33;/h18-19,22,24-26,31-32H,2-17,20-21H2,1H3,(H,34,35)(H2,28,29,33);/q;+1/p-1/t22-,24-,25+,26-;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8379682

Cytarabine ocfosfate (commercial name: Starasid) is a prodrug having stearyl group attached to phosphoric acid at 5' position of arabinose moiety of cytosine arabinoside (Ara-C). This drug is given orally. The mode of action is in the inhibition of DNA synthesis after conversion to Ara-CTP as in Ara-C. The drug is metabolized in the liver, producing the intermediate metabolite, C-C3PCA which is converted to Ara-C gradually. This property results in the maintenance of relatively long time the blood Ara-C levels. This was proved to be active clinically against acute leukemia and MDS.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA polymerase (alpha/delta/epsilon) 5 Target ID: CHEMBL2363042 Sources: http://www.rxlist.com/cytarabine-drug.htm \| http://www.bccancer.bc.ca/drug-database-site/Drug%20Index/Cytarabine_monograph_1May2014.pdf \| http://www.nature.com/leu/journal/v15/n6/full/2402114a.html	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8379682 http://adisinsight.springer.com/drugs/800000884 https://www.ncbi.nlm.nih.gov/pubmed/12162758	Primary		Approved 8429	Starasid Approved Use cytarabine ocfosfate is used clinically in Japan for the treatment of leukemia or myelodysplastic syndrome. Launch Date 1992
Myelodysplastic syndromes 58 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8379682 http://adisinsight.springer.com/drugs/800000884 https://www.ncbi.nlm.nih.gov/pubmed/12162758	Primary		Approved 8429	Starasid Approved Use cytarabine ocfosfate is used clinically in Japan for the treatment of leukemia or myelodysplastic syndrome. Launch Date 1992

PubMed

Title	Date	PubMed
[A new antileukemic drug, cytarabine ocfosfate].	1993 Sep	8379682
Response to cytarabine ocfosfate (YNK01) in a patient with chronic lymphocytic leukemia refractory to treatment with chlorambucil/prednisone, fludarabine, and prednimustine/mitoxantrone.	1996 Oct	8890711
[Late phase II study of YNK-01 (an oral prodrug of cytarabine) for hepatocellular carcinoma].	1998 Oct	9797816

Patents

Sample Use Guides

In Vivo Use Guide

For adult acute non-lymphatic leukemia: In general, for adults, take 2-6 capsules (100-300mg of the active ingredient anhydride) in 1-3 divided doses a day after meal. For myelodysplastic syndrome: In general, for adults, take 2-4 capsules (100-200mg of the active ingredient anhydride) in 1-3 divided doses a day after meal, for 2 to 3 weeks every day, then discontinue the medication for 2-3 weeks and repeat this schedule. The dosage may be adjusted according to your disease or symptoms.Strictly follow the instructions.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

CYTARABINE OCFOSFATE

Common Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-1-(5-O-(HYDROXY(OCTADECYLOXY)PHOSPHINYL)-.BETA.-D-ARABINOFURANOSYL)-, SODIUM SALT (1:1)

Systematic Name

English

Cytarabine ocfosfate [WHO-DD]

Common Name

English

CYTARABINE OCFOSPHATE

Common Name

English

FOSTEABINE SODIUM

Common Name

English

Code System Code Type Description

MESH

C061162