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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H14N3O8P
Molecular Weight 323.1965
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTARABINE 5'-PHOSPHATE

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]2O

InChI

InChIKey=IERHLVCPSMICTF-CCXZUQQUSA-N
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1

HIDE SMILES / InChI
Molecular Formula C9H14N3O8P
Molecular Weight 323.1965
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Starasid

Approved Use

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

Launch Date

7.2308163E11
Primary
Approved
8429
Starasid

Approved Use

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

Launch Date

7.2308163E11
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

Patents

20040092476
5
20040192651
5
20070037774
5
20090209481
5
7148349
5
7151092
5
7498320
5
7553826
5
8063025
5
US4812560
5
US5049663
5
US5512298
5

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 Sat Dec 16 10:48:09 UTC 2023
Edited
by admin
on Sat Dec 16 10:48:09 UTC 2023
Record UNII
Y73692GHI4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYTARABINE 5'-PHOSPHATE
Common Name English
1-.BETA.-D-ARABINOFURANOSYLCYTOSINE 5'-PHOSPHATE
Systematic Name English
PHOSPHORIC ACID MONO-((2R,3S,4S,5R)-5-(4-AMINO-2-OXO-2H-PYRIMIDIN-1-YL)-3,4-DIHYDROXY-TETRAHYDRO-FURAN-2-YLMETHYL) ESTER
Systematic Name English
NSC-99445
Code English
ARA-5'-CMP
Common Name English
1-.BETA.-D-ARABINOFURANOSYLCYTOSINE 5'-MONOPHOSPHATE
Systematic Name English
((2R,3S,4S,5R)-5-(4-AMINO-2-OXOPYRIMIDIN-1-YL)-3,4-DIHYDROXYOXOLAN-2-YL)METHYL DIHYDROGEN PHOSPHATE
Systematic Name English
ARABINOSYLCYTOSINE 5'-MONOPHOSPHATE
Common Name English
CYTOSINE, 1-.BETA.-D-ARABINOFURANOSYL-, 5'-(DIHYDROGEN PHOSPHATE)
Systematic Name English
CYTOSINE ARABINOSIDE 5'-PHOSPHATE
Common Name English
ARACYTIDINE 5'-PHOSPHATE
Common Name English
4-AMINO-1-(5-O-PHOSPHONO-.BETA.-D-ARABINOFURANOSYL)-2(1H)-PYRIMIDINONE
Systematic Name English
ARACMP
Common Name English
((2R,3S,4S,5R)-5-(4-AMINO-2-OXOPYRIMIDIN-1(2H)-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YL)METHYL DIHYDROGEN PHOSPHATE
Systematic Name English
Ara-cytidine monophosphate
Common Name English
ARACYTIDINE 5'-MONOPHOSPHATE
Common Name English
CYTOSINE ARABINOSIDE MONOPHOSPHATE
Common Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-(5-O-PHOSPHONO-.BETA.-D-ARABINOFURANOSYL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID60221012
Created by admin on Sat Dec 16 10:48:09 UTC 2023 , Edited by admin on Sat Dec 16 10:48:09 UTC 2023
PRIMARY
DRUG BANK
DB02456
Created by admin on Sat Dec 16 10:48:09 UTC 2023 , Edited by admin on Sat Dec 16 10:48:09 UTC 2023
PRIMARY
CAS
7075-11-8
Created by admin on Sat Dec 16 10:48:09 UTC 2023 , Edited by admin on Sat Dec 16 10:48:09 UTC 2023
PRIMARY
NSC
99445
Created by admin on Sat Dec 16 10:48:09 UTC 2023 , Edited by admin on Sat Dec 16 10:48:09 UTC 2023
PRIMARY
FDA UNII
Y73692GHI4
Created by admin on Sat Dec 16 10:48:09 UTC 2023 , Edited by admin on Sat Dec 16 10:48:09 UTC 2023
PRIMARY
PUBCHEM
65177
Created by admin on Sat Dec 16 10:48:09 UTC 2023 , Edited by admin on Sat Dec 16 10:48:09 UTC 2023
PRIMARY
Related Record Type Details
Structure of CYTARABINE
PARENT -> METABOLITE
PLASMA
Structure of MB-07133
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of CYTARABINE 5'-PHOSPHATE
ACTIVE MOIETY
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