(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编号: 72799
• 分子式: C43H58N4O12
• 平均质量: 822.94022
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: 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
• 别名: Rifadin; Rimactane; Rifampicin; Rifampin; Rifaldazine; Rifampicin

登记号

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

理论计算性质

• Acid pKa: 6.8984513
• 质子受体: 14
• 质子供体: 6
• LogD (pH = 5.5): 1.6852435
• LogD (pH = 7.4): 2.7622907
• Log P: 2.7698967
• 摩尔折射率: 225.5828 cm^3
• 极化性: 86.47999 Å^3
• 极化表面积: 220.15 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

安全信息

• 保存条件: -20°C

药理学性质

• 生物活性机理: Inhibits DNA dependent RNA polymerase activity in susceptible cells; RNA polymerase inhibitor

产品相关信息

• 成盐信息: Free Base
• 生物来源: Prod. from Streptomyces mediterranei
• 应用领域: Antibiotic; Antileprotic; Possesses antibacterial and antitubercular props.

详细说明

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]

参考文献

• http://en.wikipedia.org/wiki/Rifampicin
• Gadret, M. et al., Acta Cryst. B, 1975, 31, 1454, (cryst struct)
• Gallo, E.G. et al., Anal. Profiles Drug Subst., 1976, 5, 467, (rev, synth, anal)
• Girling, D.T. et al., J. Antimicrob. Chemother., 1977, 3, 115, (tox, rev)
• 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