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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 of CYTARABINE OCFOSFATE

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Starasid

Approved Use

cytarabine ocfosfate is used clinically in Japan for the treatment of leukemia or myelodysplastic syndrome.

Launch Date

1992
Primary
Starasid

Approved Use

cytarabine ocfosfate is used clinically in Japan for the treatment of leukemia or myelodysplastic syndrome.

Launch Date

1992
PubMed

PubMed

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

Sample Use Guides

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
  • Download
Name Type Language
CYTARABINE OCFOSFATE
WHO-DD  
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
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
EVMPD
SUB16415MIG
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
FDA UNII
3I7U8R8NWC
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
PUBCHEM
23671562
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
CAS
65093-40-5
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
DRUG CENTRAL
771
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
SMS_ID
100000089536
Created by admin on Fri Dec 15 19:42:28 GMT 2023 , Edited by admin on Fri Dec 15 19:42:28 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY