(7S,9E,11S,12R,13S,14R,15R,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: 72799
• Molecular Formular: C43H58N4O12
• Molecular Mass: 822.94022
• Monoisotopic Mass: 822.40512332
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H]([C@H](/C=C/O[C@]2(Oc3c(c(c4c(c(NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]1C)O)C)/C)c(c(c4c3C2=O)O)/C=N/N1CCN(CC1)C)O)O)C)C)OC)C)OC(=O)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-WLSIYKJHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,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; (7S,9E,11S,12R,13S,14R,15R,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,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• IUPAC Traditional name: rifampicin; (7S,9E,11S,12R,13S,14R,15R,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,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• Synonyms: Rifadin; Rimactane; Rifampicin; Rifampin; Rifaldazine; Rifampicin

Database IDs

• CAS Number: 13292-46-1
• PubChem SID: 162037720
• PubChem CID: 5381226

CALCULATED PROPERTIES

• 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

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: Inhibits DNA dependent RNA polymerase activity in susceptible cells; RNA polymerase inhibitor

Product Information

• Salt Data: Free Base
• Biological Source: Prod. from Streptomyces mediterranei
• Application(s): Antibiotic; Antileprotic; Possesses antibacterial and antitubercular props.

DETAILS

Selleck Chemicals - S1764

Research Area: Infection
Biological Activity:
Rifampin (Rifadin, Rimactane) is a bactericidal antibiotic agent of the rifamycin group. It is a semisynthetic compound derived from Amycolatopsis rifamycinica. RRifampicin is typically used to treat Mycobacterium infections, including tuberculosis and leprosy.With multidrug therapy used as the standard treatment of leprosy, Rifampin is always used in combination with dapsone and clofazimine to avoid eliciting agent resistance. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Rifampicin
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• Gallo, E.G. et al., Anal. Profiles Drug Subst., 1976, 5, 467, (rev, synth, anal)
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• IARC Monog., 1980, 24, 243; Suppl. 7, 71, (rev)
• Sensi, P., Chron. Drug Discovery, 1982, 1, 201, (rev)
• Sensi, P., Rev. Infect. Dis., (Suppl. 3), 1983, 5, 402, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 8227, (synonyms)
• Taguchi, M. et al., Chem. Pharm. Bull., 1988, 36, 4157, (pmr, cmr)
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 937
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 197
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, RKP000