Rifapentine hydrochlorideProduct ingredient for Rifapentine

Name
Rifapentine hydrochloride
Drug Entry
Rifapentine

Rifapentine is an antibiotic drug used in the treatment of tuberculosis. It inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme.

Accession Number
DBSALT002329
Structure
Synonyms
Not Available
UNII
5915QBW8LA
CAS Number
127923-87-9
Weight
Average: 913.5
Monoisotopic: 912.4287512
Chemical Formula
C47H65ClN4O12
InChI Key
YAXMCEWRTZAGIM-ZYFLDTFVSA-N
InChI
InChI=1S/C47H64N4O12.ClH/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);1H/b13-12-,22-17-,25-14-,48-23+;/t24-,26+,27+,28+,33-,38-,39+,43+,47-;/m0./s1
IUPAC Name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(1E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate hydrochloride
SMILES
Cl.CO[C@H]1\C=C/O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(NC(=O)\C(C)=C/C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C(\C=N\N1CCN(CC1)C1CCCC1)=C(O)C4=C3C2=O
ChemSpider
52085314
Predicted Properties
PropertyValueSource
Water Solubility0.0213 mg/mLALOGPS
logP4.83ALOGPS
logP3.7Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.99Chemaxon
pKa (Strongest Basic)7.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area220.15 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity242 m3·mol-1Chemaxon
Polarizability94.73 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon