Responsive image

Common name


Capecitabine

IUPAC name


pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

SMILES


CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O

Compound class


Antineoplastic Agents; Immunosuppressive Agents; Antimetabolites; Antimetabolites, Antineoplastic; Prodrugs; Antineoplastic and Immunomodulating Agents; Pyrimidine Analogues; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP2C9 Inducers;

Therapeutic area


For the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen. May also be used in combination with docetaxel for the treatment of metastatic breast cancer in patients who have failed to respond to, or recurred or relasped during or following anthracycline-containing chemotherapy. Capecitabine is used alone as an adjuvant therapy following the complete resection of primary tumor in patients with stage III colon cancer when monotherapy with fluroprymidine is preferred. The use or capecitabine in combination regimens for advanced gastric cancer is currently being investigated.

Common name


Capecitabine

IUPAC name


pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

SMILES


CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O

INCHI


InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1

FORMULA


C15H22FN3O6

Responsive image

Common name


Capecitabine

IUPAC name


pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

Molecular weight


359.350

clogP


0.146

clogS


-1.729

HBond Acceptor


7

HBond Donor


3

Total Polar
Surface Area


122.91

Number of Rings


2

Rotatable Bond


7

Drug ID Common name Structure CAS SMILE Frequency
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00053 (2R,3S,4S)-2-methyltetrahydrofuran-3,4-diol Responsive image O1C(C(C(C1)O)O)C 0.0014
FDBF00067 butane Responsive image CCCC 0.0680
FDBF00081 pentane Responsive image CCCCC 0.0316
FDBF00692 methyl carbamate Responsive image O(C(=O)N)C 0.0117
FDBF00808 propyl carbamate Responsive image C(CC)OC(=O)N 0.0017
FDBF00906 ethyl carbamate Responsive image CCOC(=O)N 0.0055
FDBF02504 5-fluoro-1H-pyrimidin-2-one Responsive image Fc1c[nH]c(=O)nc1 0.0003
8 , 1