sodium (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-27-olate

• ChemBase编号: 132533
• 分子式: C37H46NNaO12
• 平均质量: 719.75041
• 单一同位素质量: 719.2917702
• SMILES: Cc1c(c2c3c(cc(c2O)NC(=O)/C(=C\C=C/[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]([C@H](/C=C\O[C@@]2(C(=O)c3c1O2)C)OC)C)OC(=O)C)C)O)C)O)C)/C)[O-])O.[Na+]
• Canonical SMILES: CO[C@H]1/C=C\O[C@@]2(C)Oc3c(C2=O)c2c([O-])cc(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.[Na+]
• InChI: InChI=1S/C37H47NO12.Na/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41;/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46);/q;+1/p-1/b11-10-,14-13-,17-12-;/t16-,18+,19+,20+,25-,29-,30+,33+,37-;/m0./s1
• InChIKey: YVOFSHPIJOYKSH-DITFEXNXSA-M

名称和登记号

名称

• IUPAC标准名: sodium (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-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,^2^8]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-27-olate
• IUPAC传统名: sodium (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-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,^2^8]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-27-olate
• 别名: 利福霉素 SV 钠盐; Rifamycin SV sodium salt

登记号

• CAS号: 14897-39-3
• EC号: 238-965-7
• PubChem SID: 162226810
• PubChem CID: 71308574

理论计算性质

• Acid pKa: 7.0917516
• 质子受体: 11
• 质子供体: 5
• LogD (pH = 5.5): 4.1634398
• LogD (pH = 7.4): 3.6780498
• Log P: 4.1743436
• 摩尔折射率: 198.3485 cm^3
• 极化性: 72.22435 Å^3
• 极化表面积: 204.14 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

分子性质

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 药效: ≥900 units (dry basis)

详细说明

Sigma Aldrich - R8626

Application
Rifamycin SV is a broad-spectrum semisynthetic antimicrobial agent of the rifamycin group. It is used to study potential genes, such as rif15 and rif16, which may be involved in the conversion of rifamycin SV into rifamycin B1. It is a potential treatment for traveler’s diarrhea (TD), Clostridium difficile-associated disease (CDAD) and rheumatoid knee synovitis2,3. It is used in electron spin resonance studies4.
Biochem/physiol Actions
Rifamycin SV inhibits selective (E. coli, B. subtilis) bacterial DNA-dependent RNA polymerase by binding to the polymerase β-subunit, a mechanism similar to rifabutin. It acts as a selective cytochrome P450 3A4 inducer. It has limited oral absorption that is active against Gram-positive bacteria and is moderately active against Gram-negative organisms2.