Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00416
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| Drug Name |
Cytarabine
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| Synonyms |
(beta-D-Arabinofuranosyl)cytosine; 1-.beta.-D-arabinofuranosyl-cytosine; 1-Arabinofuranosylcytosine; 1-beta-D-Arabinofaranosylcytosine; 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone; 1-beta-D-Arabinofuranosylcytosine; 1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside; 1-beta-D-Arabinosylcytosine; 1beta-Arabinofuranasylcytosine; 1beta-D-Arabinofuranosylcytosine; 1beta-D-Arabinosylcytosine; 2(1H)-Pyrimidinone, 4-amino-1-D-arabinofuranosyl-[CAS]; 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin; 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin [Czech]; 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine; 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone; 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon; 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinon [Czech]; 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone; 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one; 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one; AR3; Alexan; Ara-C; Ara-C, Cytosine Arabinoside, Cytosar-U, Cytarabine; Ara-Cytidine; AraC; Arabinocytidine; Arabinofuranosylcytosine; Arabinosyl Cytosine; Arabinosylcytosine; Arabitin; Aracytidine; Aracytin; Aracytine; Arafcyt; BTB15125; Beta-Ara C; Beta-Arabinosylcytosine; Beta-D-Arabinosylcytosine; Beta-cytosine arabinoside; CHX 3311; CYTARABINE (SEE ALSO CYTARABINE HYDROCHLORIDE 69-74-9); Citarabina; Citarabina [INN-Spanish]; Cytarabin; Cytarabina; Cytarabine (JP15/USP/INN); Cytarabine [USAN:INN:BAN:JAN]; Cytarabine liposome injection; Cytarabinoside; Cytarabinum; Cytarabinum [INN-Latin]; Cytarbel; Cytonal; Cytosar; Cytosar-U; Cytosar-U (TN); Cytosine 1-beta-D-arabinofuranoside; Cytosine arabinofuranoside; Cytosine arabinose; Cytosine arabinoside; Cytosine arabinoside (VAN); Cytosine beta-D-arabinofuranoside; Cytosine beta-D-arabinofuranoside hydrochloride; Cytosine beta-D-arabinoside; Cytosine, beta-D-arabinoside; Cytosine-1-beta-D-arabinofuranoside; Cytosine-beta-D-arabinofuranoside; Cytosine-beta-arabinoside; Cytosinearabinoside; DepoCyte; Depocyt; Depocyt (TN); Depocyt (liposomal); Erpalfa; Intrathecal (injected into the spinal fluid) DepoCyt; Intrathecal cytarabine (also known as ara-C); Iretin; Spongocytidine; Tarabine; U 19920A; U-19,920; U-19920; Udicil
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| Drug Type |
Small molecular drug
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| Indication | Acute lymphoblastic leukemia [ICD11:2B33.0] | Approved | [1] | |||
| Chronic myelogenous leukemia [ICD11:2A20.0] | Approved | [1] | ||||
| Acute myeloid leukemia [ICD11:2A60] | Approved | [1] | ||||
| Therapeutic Class |
Anticancer Agents
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| Structure |
|
 |
||||
| 3D MOL | 2D MOL | |||||
| Formula |
C9H13N3O5
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| Canonical SMILES |
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
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| 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
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| InChIKey |
UHDGCWIWMRVCDJ-CCXZUQQUSA-N
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| CAS Number |
CAS 147-94-4
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| Pharmaceutical Properties | Molecular Weight | 243.22 | Topological Polar Surface Area | 129 | ||
| Heavy Atom Count | 17 | Rotatable Bond Count | 2 | |||
| Hydrogen Bond Donor Count | 4 | Hydrogen Bond Acceptor Count | 5 | |||
| XLogP |
-2.1
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| PubChem CID | ||||||
| PubChem SID |
103210760
,103986361
,104253284
,104311532
,11528303
,11533128
,117529237
,118048876
,12146044
,124648720
,124757405
,124799562
,14774115
,15196510
,24858315
,24892435
,26527898
,26719755
,29215144
,29225249
,3260118
,46386862
,46505879
,47193873
,47573376
,48415837
,49831046
,50105698
,53787662
,56310997
,56311029
,56312269
,56312943
,56313129
,56313612
,5877
,598052
,76890970
,7847236
,7885952
,7979015
,8153933
,829245
,83110442
,87558791
,90341066
,92308449
,92309014
,93166529
,93167157
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| ChEBI ID |
ChEBI:28680
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | 1-Oct | Transporter Info | Organic cation transporter 1 | Substrate | [2] | |
| CNT1 | Transporter Info | Concentrative nucleoside transporter 1 | Substrate | [3] | ||
| ENT1 | Transporter Info | Equilibrative nucleoside transporter 1 | Substrate | [3] | ||
| ENT2 | Transporter Info | Equilibrative nucleoside transporter 2 | Substrate | [3] | ||
| OCTN1 | Transporter Info | Organic cation/carnitine transporter 1 | Substrate | [4] | ||
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [5] | ||
| References | ||||||
| 1 | Cytarabine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | |||||
| 3 | FLT3 is implicated in cytarabine transport by human equilibrative nucleoside transporter 1 in pediatric acute leukemia. Oncotarget. 2016 Aug 2;7(31):49786-49799. | |||||
| 4 | OCTN1 Is a High-Affinity Carrier of Nucleoside Analogues. Cancer Res. 2017 Apr 15;77(8):2102-2111. | |||||
| 5 | Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64. | |||||
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