Cytarabine

Details

• Internal ID: fe3a563f-e9dc-44d0-b32c-0af4b204222b
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleosides
• IUPAC Name: 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• InChI: InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
• InChI Key: UHDGCWIWMRVCDJ-CCXZUQQUSA-N
• Popularity: 38,346 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃N₃O₅
• Molecular Weight: 243.22 g/mol
• Exact Mass: 243.08552052 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.56
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 147-94-4
• Ara-C
• Cytosine arabinoside
• Arabinocytidine
• Aracytidine
• Cytarabinoside
• Spongocytidine
• Aracytin
• Cytosar-U
• Depocyt
• Alexan
• Udicil
• Arabitin
• Aracytine
• Cytarabina
• Tarabine
• Arafcyt
• Erpalfa
• Arabinofuranosylcytosine
• 1-beta-D-Arabinofuranosylcytosine
• arabinocytosine
• Cytarabinum
• DepoCyte
• Arabinosylcytosine
• Cytarabin
• Cytosar
• Cytosine beta-D-arabinofuranoside
• Cytosinearabinoside
• Citarabina
• Depocyt (liposomal)
• beta-D-Arabinosylcytosine
• Cytosine arabinofuranoside
• Cytosine beta-D-arabinoside
• 4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
• Cytarabinum [INN-Latin]
• Arabinoside C
• 1beta-D-Arabinosylcytosine
• Citarabina [INN-Spanish]
• Cytosine-1-beta-D-arabinofuranoside
• AraC
• Cytosine arabinose
• 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone
• 1beta-Arabinofuranasylcytosine
• Iretin
• Cytosine 1-beta-D-arabinofuranoside
• 1beta-D-Arabinofuranosylcytosine
• 1-beta-D-Arabinofaranosylcytosine
• beta-Arabinosylcytosine
• Ara-Cytidine
• U 19920A
• Beta-cytosine arabinoside
• Cytosine-beta-arabinoside
• Cytosine-beta-D-arabinofuranoside
• cytarabine liposome
• 1-Arabinofuranosylcytosine
• CHX 3311
• CCRIS 913
• U-19,920
• 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one
• Arabinofuranosyl Cytidine
• Cytosine, 1-beta-D-arabinosyl-
• 1-beta-D-Arabinosylcytosine
• HSDB 3049
• 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
• EINECS 205-705-9
• 1-(arabinofuranosyl)cytosine
• Cyclocide
• Cytosine, 1-beta-D-arabinofuranosyl-
• NSC 287459
• UNII-04079A1RDZ
• 1-beta-arabinofuranosylcytosine
• U-19920
• DTXSID3022877
• CHEBI:28680
• AI3-52329
• 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin
• 04079A1RDZ
• 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-
• CHEMBL803
• NSC-287459
• MK 8242
• 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon
• 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• C9H13N3O5
• DTXCID702877
• 2(1H)-Pyrimidinone, 4-amino-1-.beta.-D-arabinofuranosyl-
• AR3
• Cytonal
• NCI-C04728
• VYXEOS COMPONENT CYTARABINE
• 1-beta-D-arabinofuranosyl-cytosine
• 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine
• AC-1075
• beta-Ara C
• Cytarabine [USAN:USP:INN:BAN:JAN]
• (beta-D-Arabinofuranosyl)cytosine
• NCGC00093356-03
• 2(1H)-Pyrimidinone, 4-amino-1-y-D-arabinofuranosyl- [CAS]
• Cytarbel
• (Arabinofuranosyl)cytosine
• Cytarabinum (INN-Latin)
• MFCD00066487
• Citarabina (INN-Spanish)
• CYTARABINE (MART.)
• CYTARABINE [MART.]
• CYTARABINE (USP-RS)
• CYTARABINE [USP-RS]
• Citozar
• ara-Cytosine
• Cytosine arabinoside (VAN)
• Tarabine PFS
• CYTARABINE (EP MONOGRAPH)
• CYTARABINE (USP IMPURITY)
• CYTARABINE [EP MONOGRAPH]
• CYTARABINE [USP IMPURITY]
• Cytosine-1-beta-arabinofuranoside
• CYTARABINE (USP MONOGRAPH)
• CYTARABINE [USP MONOGRAPH]
• Ara-cell
• Cytarabine (USAN:USP:INN:BAN:JAN)
• cytarabine liposome injection
• Arabinosyl Cytosine
• Cytosine, beta-D-arabinoside
• CAS-147-94-4
• SMR000449317
• Depocyt (TN)
• Arabinoside, Cytosine
• 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Cytosine b-D-arabinofuranoside
• Cytartbine
• Arabine
• 1-.beta.-D-Arabinofuranosylcytosine
• Cytarabine; 4-amino-1-beta-d-arabinofuranosylpyrimidin-2(1H)-one
• SR-01000075773
• NSC287459
• 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon [Czech]
• 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [Czech]
• 1-(beta-d-arabinofuranosyl)cytosine
• 1-.beta.-D-arabinofuranosyl-cytosine
• 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone
• U-19920 A
• cytarabine ocphosphate
• 1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside
• beta -arabinosylcytosine
• CYTARABINE [MI]
• U 19920
• CYTARABINE [INN]
• CYTARABINE [JAN]
• CYTARABINE [HSDB]
• CYTARABINE [USAN]
• beta -cytosine arabinoside
• beta -D-arabinosylcytosine
• Cytosine-beta -arabinoside
• CYTARABINE [VANDF]
• SCHEMBL3140
• 1beta -D-Arabinosylcytosine
• CYTARABINE [WHO-DD]
• CYTARABINE [WHO-IP]
• BIDD:PXR0139
• Lopac0_000316
• MLS000758310
• MLS001066340
• MLS001424023
• 1-beta-D-Arabinosyl-Cytosine
• BIDD:GT0371
• CYTARABINE [EMA EPAR]
• Cytosine, beta -D-arabinoside
• 1beta -Arabinofuranasylcytosine
• Cytarabine (JP17/USP/INN)
• GTPL4827
• 1-ss-D-Arabinofuranosylcytosine
• 2(1H)-Pyrimidinone, 4-amino-1beta-D-arabinofuranosyl-
• CYTARABINE [ORANGE BOOK]
• SCHEMBL22591193
• SCHEMBL23152019
• 1beta -D-Arabinofuranosylcytosine
• BETA-CYTOSINE, ARABINOSIDE
• L01BC01
• Cytosine, 1-beta -D-arabinosyl-
• 1-beta -d-arabinofuranosylcytosine
• 1-beta-D-arabinofuranosyl cytosine
• Cytosine-beta -D-arabinofuranoside
• HMS2051K19
• HMS2090A18
• HMS2230M16
• HMS3713N12
• 1-beta -D-Arabinofaranosylcytosine
• CYTARABINE LIPOSOME [VANDF]
• CYTARABINUM [WHO-IP LATIN]
• BCP02876
• Tox21_111203
• Tox21_301971
• BDBM50087289
• CCG-51297
• s1648
• AKOS007930145
• AKOS015896896
• AM84428
• Cytosine, 1-beta -D-arabinofuranosyl-
• DB00987
• KS-5063
• NC00070
• SDCCGSBI-0050304.P002
• NCGC00093356-04
• NCGC00093356-05
• NCGC00093356-06
• NCGC00093356-19
• NCGC00142483-02
• NCGC00255381-01
• 1(BETA-D-ARABINOFURANOSYL)CYTOSINE
• BA164339
• HY-13605
• SRI-10828-19
• SRI-10828-20
• SRI-10828_24
• WR-28453
• SL-000002
• U 19,920A
• C2035
• SW197450-5
• C02961
• D00168
• EN300-118320
• 1-BETA-D-ARABINOFURANOSYLCYTOSINE; ARA-C
• A808710
• Q180983
• SR-01000721860
• J-520199
• J-700005
• J-700166
• SR-01000075773-3
• SR-01000075773-5
• SR-01000721860-6
• U 19,920
• 1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone
• 2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl
• BRD-K33106058-001-07-7
• BRD-K33106058-003-20-6
• 1-BETA-D-ARABINOSYL-4-AMINO-2(1H)PYRIMIDINONE
• 2(1H)-Pyrimidinone, 4-amino-1beta -D-arabinofuranosyl-
• Cytosine -D-arabinofuranoside;Cytosine Arabinoside;Ara-C
• Z1511499171
• 2(1H)-Pyrimidinone, 4-amino-1-beta -D-arabinofuranosyl-
• Cytarabine, European Pharmacopoeia (EP) Reference Standard
• Cytarabine, United States Pharmacopeia (USP) Reference Standard
• Cytosine beta-D-arabinofuranoside, crystalline, >=90% (HPLC)
• Cytosine beta-D-arabinofuranoside, Vetec(TM) reagent grade, 90%
• Cytarabine, Pharmaceutical Secondary Standard; Certified Reference Material
• 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
• Cytosine -D-arabinofuranoside hydrochloride;Cytosine Arabinoside hydrochloride;Ara-C hydrochloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5214	52.14%
Caco-2	-	0.9072	90.72%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Nucleus	0.4886	48.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9461	94.61%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9797	97.97%
P-glycoprotein inhibitior	-	0.9526	95.26%
P-glycoprotein substrate	-	0.9737	97.37%
CYP3A4 substrate	-	0.6285	62.85%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	-	0.9609	96.09%
CYP2C9 inhibition	-	0.9638	96.38%
CYP2C19 inhibition	-	0.9489	94.89%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	-	0.9543	95.43%
CYP2C8 inhibition	-	0.9860	98.60%
CYP inhibitory promiscuity	-	0.9810	98.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.4707	47.07%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9761	97.61%
Skin irritation	-	0.7802	78.02%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7018	70.18%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	+	0.9502	95.02%
skin sensitisation	-	0.8566	85.66%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.4497	44.97%
Acute Oral Toxicity (c)	III	0.7926	79.26%
Estrogen receptor binding	-	0.5448	54.48%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5416	54.16%
Glucocorticoid receptor binding	+	0.6838	68.38%
Aromatase binding	+	0.5341	53.41%
PPAR gamma	+	0.7112	71.12%
Honey bee toxicity	-	0.9394	93.94%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.9006	90.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5023	Q00987	p53-binding protein Mdm-2	20 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	39.8 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	73.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	96.07%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.60%	96.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	92.18%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	89.22%	98.46%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.92%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.35%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.83%	86.33%

Plants that contains it

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Cross-Links

• PubChem: 6253
• LOTUS: LTS0190344
• wikiData: Q180983