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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

Molecular Formula	C27H49N3O8P
Molecular Weight	574.667
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
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

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:42:28 GMT 2023` Edited by `admin` on `Fri Dec 15 19:42:28 GMT 2023`
Record UNII	3I7U8R8NWC
Record Status	`Validated (UNII)`
Record Version

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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