rifapentine   Click here for help

GtoPdb Ligand ID: 12014

Synonyms: DL 473 | MDL 473 | Priftin®
Approved drug PDB Ligand
rifapentine is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Rifapentine is a semisynthetic derivative of rifamycin and belongs to the ansamycin group of antibacterial compounds [1]. Rifapentine is on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an oral antituberculosis medication.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 6
Topological polar surface area 220.15
Molecular weight 876.45
XLogP 5.25
No. Lipinski's rules broken 3
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Canonical SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C4CCCC4)c(c(c2c(c3C)O)O)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C
Isomeric SMILES C[C@H]1/C=C/C=C(\C(=O)Nc2c(c(c3c(c2O)c(c(c2c3C(=O)[C@](O2)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N1CCN(CC1)C1CCCC1)/C
InChI InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1998))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
International Nonproprietary Names Click here for help
INN number INN
4765 rifapentine
Synonyms Click here for help
DL 473 | MDL 473 | Priftin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rifapentine
Other databases
CAS Registry No. 61379-65-5 (source: Scifinder)
ChEMBL Ligand CHEMBL1660
DrugBank Ligand DB01201
DrugCentral Ligand 2378
GtoPdb PubChem SID 464244155
PubChem CID 135403821
Search Google for chemical match using the InChIKey WDZCUPBHRAEYDL-GZAUEHORSA-N
Search Google for chemicals with the same backbone WDZCUPBHRAEYDL
Search PubMed clinical trials rifapentine
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Search PubMed titles/abstracts rifapentine
UniChem Compound Search for chemical match using the InChIKey WDZCUPBHRAEYDL-GZAUEHORSA-N
UniChem Connectivity Search for chemical match using the InChIKey WDZCUPBHRAEYDL-GZAUEHORSA-N
Wikipedia Rifapentine