
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

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 |
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C(C)C | 0.2412 |
FDBF00053 | (2R,3S,4S)-2-methyltetrahydrofuran-3,4-diol |
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O1C(C(C(C1)O)O)C | 0.0014 |
FDBF00067 | butane |
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CCCC | 0.0680 |
FDBF00081 | pentane |
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CCCCC | 0.0316 |
FDBF00692 | methyl carbamate |
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O(C(=O)N)C | 0.0117 |
FDBF00808 | propyl carbamate |
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C(CC)OC(=O)N | 0.0017 |
FDBF00906 | ethyl carbamate |
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CCOC(=O)N | 0.0055 |
FDBF02504 | 5-fluoro-1H-pyrimidin-2-one |
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Fc1c[nH]c(=O)nc1 | 0.0003 |