(7S,9E,11S,12R,13S,14S,15S,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate

• ChemBase ID: 917
• Molecular Formular: C43H58N4O12
• Molecular Mass: 822.94022
• Monoisotopic Mass: 822.40512332
• SMILES: [C@H]1([C@H]([C@H](OC(=O)C)[C@H]([C@@H](OC)/C=C/O[C@]2(Oc3c(c(c4c(c(NC(=O)/C(=C\C=C\[C@@H]([C@H](O)[C@H]1C)C)/C)c(c(c4c3C2=O)O)/C=N/N1CCN(CC1)C)O)O)C)C)C)C)O
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C)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
• InChI: InChI=1S/C43H58N4O12/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)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25-,29-,34-,35-,39+,43-/m0/s1
• InChIKey: JQXXHWHPUNPDRT-DLTKJSJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14S,15S,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14S,15S,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• Brand Name: Archidyn; L-5103 Lepetit; R/AMP; RAMP; Rfamipicin; Rifa; Rifadin; Rifadin IV; Rifadine; Rifagen; Rifaldazin; Rifaldazine; Rifaldin; Rifampicin; Rifampicin SV; Rifamycin; Rifamycin Amp; Rifaprodin; Rifoldin; Rifoldine; Riforal; Rimactan; Rimactane; Rimactin; Rimazid; Rofact; Tubocin
• Synonyms: RFP; Rifampin

Database IDs

• CAS Number: 13292-46-1
• PubChem SID: 160964380
• PubChem CID: 44419043

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8984513
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 1.6852435
• LogD (pH = 7.4): 2.7622907
• Log P: 2.7698967
• Molar Refractivity: 225.5828 cm^3
• Polarizability: 86.47999 Å^3
• Polar Surface Area: 220.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.85
• LOG S: -4.3
• Solubility (Water): 4.13e-02 g/l

PROPERTIES

Physical Property

• Solubility: 1.4 mg/mL
• Hydrophobicity(logP): 2.7

DETAILS

DrugBank - DB01045

• Drug Groups: approved
• Description: 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)
• Indication: For the treatment of Tuberculosis and Tuberculosis-related mycobacterial infections.
• Pharmacology: Rifampin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. Because of rapid emergence of resistant bacteria, use is restricted to treatment of mycobacterial infections and a few other indications. Rifampin is well absorbed when taken orally and is distributed widely in body tissues and fluids, including the CSF. It is metabolized in the liver and eliminated in bile and, to a much lesser extent, in urine, but dose adjustments are unnecessary with renal insufficiency.
• Toxicity: LD₅₀=1570 mg/kg (rat), chronic exposure may cause nausea and vomiting and unconsciousness
• Affected Organisms: Mycobacteria; Various gram-negative and gram-positive eubacteria
• Biotransformation: Primarily hepatic, rapidly deacetylated.
• Absorption: Well absorbed from gastrointestinal tract.
• Half Life: 3.35 (+/- 0.66) hours
• Protein Binding: 89%
• Elimination: Less than 30% of the dose is excreted in the urine as rifampin or metabolites.
• Clearance: * 0.19 +/- 0.06 L/hr/kg [300 mg IV]; * 0.14 +/- 0.03 L/hr/kg [600 mg IV]
• References: Baysarowich J, Koteva K, Hughes DW, Ejim L, Griffiths E, Zhang K, Junop M, Wright GD: Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4886-91. Epub 2008 Mar 18. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Baysarowich J, Koteva K, Hughes DW, Ejim L, Griffiths E, Zhang K, Junop M, Wright GD: Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4886-91. Epub 2008 Mar 18. Pubmed