Rifampicin sodiumProduct ingredient for Rifampicin

Name
Rifampicin sodium
Drug Entry
Rifampicin

A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)

Accession Number
DBSALT001014
Structure
Thumb
Synonyms
Not Available
UNII
GPE7477YEK
CAS Number
38776-75-9
Weight
Average: 844.935
Monoisotopic: 844.38706757
Chemical Formula
C43H57N4NaO12
InChI Key
PPGHYTPFGILTSZ-LGIBZRBQSA-M
InChI
InChI=1S/C43H58N4O12.Na/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49;/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55);/q;+1/p-1/b12-11-,19-14-,22-13-,44-20+;/t21-,23+,24+,25+,29-,34-,35+,39+,43-;/m0./s1
IUPAC Name
sodium (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(1E)-[(4-methylpiperazin-1-yl)imino]methyl]-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-27-olate
SMILES
[Na+].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(C)CC1)=C([O-])C4=C3C2=O
ChemSpider
52085882
Predicted Properties
PropertyValueSource
Water Solubility0.0447 mg/mLALOGPS
logP4.15ALOGPS
logP2.95ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)6.8ChemAxon
pKa (Strongest Basic)7.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area222.98 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity236.13 m3·mol-1ChemAxon
Polarizability87.27 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon