CYTARABINE 5'-PHOSPHATE

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 Search

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
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:48:09 GMT 2023` Edited by `admin` on `Sat Dec 16 10:48:09 GMT 2023`
Record UNII	Y73692GHI4
Record Status	`Validated (UNII)`
Record Version

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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