Capecitabine

An orally administered fluoropyrimidine anticancer agent used in the treatment of colorectal, breast, gastric, and other selected cancers. Capecitabine undergoes enzymatic conversion to 5-fluorouracil (5-FU), which is further metabolized to active nucleotides that inhibit thymidylate synthase and interfere with DNA and RNA synthesis. Its activation pathway involves carboxylesterase, cytidine deaminase, and thymidine phosphorylase

CAS Number: 154361-50-9

Molecular Mass: 359.35 g/mol

Formula: C₁₅H₂₂FN₃O₆

Smiles: CCCCCOC(=O)Nc1nc(=O)n([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)cc1F

Synonymes:

Capecitabine, CAPECITABINE, 154361-50-9, Xeloda, Capecitibine, Capiibine, Captabin, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine, capecitabina, Capecytabine, Capecitabine Sun, Capecitabine Teva, Capecitabine Medac, Capecitabine Accord, capecitabinum, Capecitabin, Ecansya, Ro 09-1978/000, N(4)-Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine, Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate, 5'-Deoxy-5-fluoro-N-((pentyloxy)carbonyl)cytidine, DTXSID3046451, Ro-091978000, 6804DJ8Z9U, NSC-759853, (1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester, Carbamic acid, (1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-, pentyl ester, DTXCID1026451, CHEBI:31348, RO-09-1978000, Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate, pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate, NSC712807, Pentyl (1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate, pentyl N-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate, Capecitabine 150mg, Capecitabine 500mg, RefChem:56770, Capecitabine Tablets, 150 mg, Capecitabine Tablets, 500 mg, L01BC06, 5'-Deoxy-5-fluoro-N-((pentyloxy)carbonyl)-cytidine, Ro 09-1978, Pentyl (1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate, pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate, Cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-, Caxeta, Xabine, Capecitabine [USAN], Ro-09-1978-000, 5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine, Capecitabine (Xeloda), SMR002530052, Xeloda (TN), CAS-154361-50-9, Cytidine, 5'-deoxy-5-fluoro-N-((pentyloxy)carbonyl)-, R340, Capecitabine?, UNII-6804DJ8Z9U, Capecitabine CRS, HSDB 7656, Capecitabine, API, NCGC00164569-01, Capecitabine [USAN:USP:INN:BAN], RG-340, Ro-09-1978, Capecitabine (Standard), CAPECITABINE [MI], R-340, CAPECITABINE [INN], CAPECITABINE [JAN], CAPECITABINE [HSDB], Xelox component capecitabine, SCHEMBL8153, CAPECITABINE [VANDF], CHEMBL1773, CAPECITABINE [MART.], MLS003915642, MLS004774137, CAPECITABINE [USP-RS], CAPECITABINE [WHO-DD], Capecitabine (JAN/USP/INN), GTPL6799, orb1308702, orb3141267, CAPECITABINE [EMA EPAR], Capecitabine - Bio-X trade mark, Capecitabine, analytical standard, HY-B0016R, Capecitabine, >=98% (HPLC), EX-A835, CAPECITABINE [ORANGE BOOK], GLXC-03327, CAPECITABINE [EP MONOGRAPH], CAPECITABINE [USP IMPURITY], HY-B0016, MSK10360, XELIRI COMPONENT CAPECITIBINE, CAPECITABINE [USP MONOGRAPH], Tox21_112198, EBC-07649, s1156, AKOS015920130, Tox21_112198_1, BS-1000, CCG-264841, CS-0768, DB01101, ND09160, NSC 759853, NCGC00164569-02, NCGC00164569-05, NCGC00164569-11, BC164277, BP-58647, pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-2-oxo-pyrimidin-4-yl]carbamate, NS00000464, D01223, n4-pentyloxycarbonyl-5'-deoxy-5-fluorocytidine, AB01274776-01, AB01274776-02, AB01274776_04, 5-Fluoro-N4-(pentyloxycarbonyl)-5'-deoxycytidine, F048966, F404586, Q420207, SR-01000931255, SR-01000931255-3, BRD-K61192372-001-05-5, BRD-K61192372-001-08-9, Z1501480421, Capecitabine, European Pharmacopoeia (EP) Reference Standard, Capecitabine, United States Pharmacopeia (USP) Reference Standard, Capecitabine, Pharmaceutical Secondary Standard, Certified Reference Material, [1-(5-Deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl] carbamic a cid pentyl ester, 5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine, pentyl (1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate, 958887-39-3, CARBAMIC ACID, (1-(5-DEOXY-.BETA.-D-RIBOFURANOSYL)-5-FLUORO-1,2-DIHYDRO-2-OXO-4-PYRIMIDINYL)-, PENTYL ESTER, pentyl 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate, PENTYL 1-(5-DEOXY-.BETA.-D-RIBOFURANOSYL)-5-FLUORO-1,2-DIHYDRO-2-OXO-4-PYRIMIDINECARBAMATE

Bioactivity: Antineoplastic antimetabolite; fluoropyrimidine prodrug of 5-fluorouracil

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.1	-	8.38	[69]
1-Butanol	283.03	-	12.0	[69]
1-Butanol	288.02	-	17.8	[69]
1-Butanol	293.53	-	28.0	[69]
1-Butanol	298.0	-	41.86	[69]
1-Butanol	303.15	-	63.2	[69]
1-Butanol	308.25	-	94.74	[69]
1-Butanol	312.35	-	140.2	[69]
1-Butanol	317.4	-	206.0	[69]
1-Butanol	322.49	-	318.0	[69]
1-Hexanol	278.1	-	5.26	[69]
1-Hexanol	284.33	-	8.44	[69]
1-Hexanol	287.97	-	11.0	[69]
1-Hexanol	293.85	-	17.0	[69]
1-Hexanol	297.6	-	23.0	[69]
1-Hexanol	303.55	-	36.12	[69]
1-Hexanol	308.55	-	50.01	[69]
1-Hexanol	313.15	-	69.87	[69]
1-Hexanol	317.75	-	97.05	[69]
1-Hexanol	322.25	-	135.6	[69]
1-Octanol	278.65	-	5.09	[69]
1-Octanol	283.0	-	6.9	[69]
1-Octanol	287.98	-	9.2	[69]
1-Octanol	292.95	-	12.6	[69]
1-Octanol	298.35	-	17.4	[69]
1-Octanol	302.94	-	23.0	[69]
1-Octanol	307.5	-	29.85	[69]
1-Octanol	312.35	-	39.42	[69]
1-Octanol	317.05	-	51.55	[69]
1-Octanol	322.05	-	70.3	[69]
1-Pentanol	278.2	-	6.7	[69]
1-Pentanol	282.97	-	10.4	[69]
1-Pentanol	288.26	-	17.1	[69]
1-Pentanol	292.64	-	23.8	[69]
1-Pentanol	297.33	-	33.76	[69]
1-Pentanol	302.27	-	48.8	[69]
1-Pentanol	307.06	-	68.63	[69]
1-Pentanol	312.04	-	98.19	[69]
1-Pentanol	316.78	-	136.8	[69]
1-Pentanol	321.47	-	190.2	[69]
1-Propanol	278.0	-	11.7	[69]
1-Propanol	283.06	-	18.0	[69]
1-Propanol	287.98	-	26.7	[69]
1-Propanol	292.87	-	42.7	[69]
1-Propanol	297.33	-	64.01	[69]
1-Propanol	302.29	-	99.65	[69]
1-Propanol	307.07	-	151.1	[69]
1-Propanol	312.14	-	232.9	[69]
1-Propanol	316.88	-	345.9	[69]
1-Propanol	321.47	-	516.9	[69]
2-Butanol	278.15	-	4.0	[69]
2-Butanol	283.17	-	6.33	[69]
2-Butanol	288.13	-	10.2	[69]
2-Butanol	293.35	-	16.9	[69]
2-Butanol	298.44	-	25.4	[69]
2-Butanol	302.9	-	36.3	[69]
2-Butanol	307.65	-	54.6	[69]
2-Butanol	312.44	-	80.93	[69]
2-Butanol	317.25	-	118.2	[69]
2-Butanol	321.9	-	169.4	[69]
Ethanol	278.25	-	62.6	[69]
Ethanol	282.86	-	77.57	[69]
Ethanol	287.85	-	107.0	[69]
Ethanol	292.84	-	156.0	[69]
Ethanol	297.75	-	224.2	[69]
Ethanol	302.55	-	307.0	[69]
Ethanol	307.25	-	439.5	[69]
Ethanol	312.14	-	620.4	[69]
Ethanol	317.35	-	872.7	[69]
Ethanol	322.13	-	1186.0	[69]
Ethyl acetate	278.15	-	11.0	[70]
Ethyl acetate	283.15	-	14.6	[70]
Ethyl acetate	288.15	-	19.3	[70]
Ethyl acetate	293.15	-	25.09	[70]
Ethyl acetate	298.15	-	33.84	[70]
Ethyl acetate	303.15	-	41.04	[70]
Ethyl acetate	308.15	-	54.42	[70]
Ethyl acetate	313.15	-	69.2	[70]
Ethyl acetate	318.15	-	86.02	[70]
Ethyl acetate	323.15	-	109.3	[70]
Ethylene Glycol	278.65	-	66.0	[69]
Ethylene Glycol	283.15	-	82.1	[69]
Ethylene Glycol	287.95	-	112.0	[69]
Ethylene Glycol	293.0	-	138.0	[69]
Ethylene Glycol	297.95	-	176.3	[69]
Ethylene Glycol	302.95	-	230.9	[69]
Ethylene Glycol	307.65	-	291.8	[69]
Ethylene Glycol	312.1	-	362.8	[69]
Ethylene Glycol	316.85	-	449.3	[69]
Ethylene Glycol	322.25	-	608.1	[69]
Heptanol	278.0	-	4.65	[69]
Heptanol	283.15	-	6.43	[69]
Heptanol	288.33	-	9.23	[69]
Heptanol	292.53	-	12.0	[69]
Heptanol	297.63	-	16.6	[69]
Heptanol	303.3	-	23.4	[69]
Heptanol	308.35	-	32.02	[69]
Heptanol	313.25	-	43.2	[69]
Heptanol	318.05	-	57.51	[69]
Heptanol	322.85	-	76.32	[69]
Isoamyl Alcohol	278.25	-	9.05	[69]
Isoamyl Alcohol	282.97	-	12.7	[69]
Isoamyl Alcohol	288.76	-	19.0	[69]
Isoamyl Alcohol	292.64	-	24.6	[69]
Isoamyl Alcohol	297.33	-	33.83	[69]
Isoamyl Alcohol	302.27	-	46.73	[69]
Isoamyl Alcohol	307.06	-	64.02	[69]
Isoamyl Alcohol	312.04	-	88.81	[69]
Isoamyl Alcohol	316.78	-	120.7	[69]
Isoamyl Alcohol	321.47	-	163.5	[69]
Isobutanol	278.26	-	4.74	[69]
Isobutanol	283.15	-	7.08	[69]
Isobutanol	288.1	-	11.4	[69]
Isobutanol	293.38	-	18.0	[69]
Isobutanol	298.02	-	27.0	[69]
Isobutanol	302.85	-	41.65	[69]
Isobutanol	307.4	-	60.75	[69]
Isobutanol	312.25	-	90.61	[69]
Isobutanol	316.95	-	132.0	[69]
Isobutanol	321.95	-	195.5	[69]
Isopropanol	277.98	-	5.26	[69]
Isopropanol	283.49	-	7.61	[69]
Isopropanol	288.07	-	11.4	[69]
Isopropanol	293.16	-	17.4	[69]
Isopropanol	297.34	-	24.9	[69]
Isopropanol	302.29	-	37.0	[69]
Isopropanol	307.07	-	53.8	[69]
Isopropanol	312.14	-	79.5	[69]
Isopropanol	316.88	-	112.9	[69]
Isopropanol	321.47	-	160.0	[69]
Water	278.25	-	18.0	[69]
Water	283.2	-	20.0	[69]
Water	288.3	-	20.0	[69]
Water	293.25	-	21.9	[69]
Water	298.25	-	23.9	[69]
Water	302.8	-	25.8	[69]
Water	308.0	-	27.7	[69]
Water	312.95	-	29.7	[69]
Water	317.65	-	31.7	[69]
Water	322.75	-	33.6	[69]
tert-Butanol	299.65	-	29.7	[69]
tert-Butanol	302.75	-	36.5	[69]
tert-Butanol	307.43	-	52.68	[69]
tert-Butanol	312.2	-	75.37	[69]
tert-Butanol	317.04	-	111.7	[69]
tert-Butanol	321.65	-	161.7	[69]

Molecule 3D descriptors

Descriptor	Value
PMI1	810.2326
PMI2	6906.3996
PMI3	7399.9666
NPR1	0.1095
NPR2	0.9333
RadiusOfGyration	4.5862
InertialShapeFactor	0.0012
Eccentricity	0.9940
Asphericity	0.7075
SpherocityIndex	0.0860
PBF	0.7316