Rifampicin
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| Category | Antibiotics |
| Catalog number | BBF-04562 |
| CAS | 13292-46-1 |
| Molecular Weight | 822.94 |
| Molecular Formula | C43H58N4O12 |
| Purity | 95% by HPLC |
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Description
It is a semi-synthetic antibiotic of the rifamycin group. It is an inhibitor of bacterial RNA polymerase and has antibacerial activity.
Specification
| Synonyms | Rimactane; 3-[[(4-Methyl-1-piperazin-yl)imino]methyl]rifamycin; Abrifam; Eremfat; Famcin; NSC 113926; Rifa; Rifacap; Rifadin; Rifadine; Rifaldazine; Rifampicin SV; Rifamycin AMP; Rifaprodin; Rifoldin; Riforal; Rimactan; Rimactane; Rimapen; Sinerdol; Tubocin |
| Storage | Store at RT |
| 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)-(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate |
| Canonical SMILES | CC1C=CC=C(C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C=NN5CCN(CC5)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 |
| InChI Key | JQXXHWHPUNPDRT-WLSIYKJHSA-N |
| Source | Semi-synthetic: Amycolatopsis Rifamycinica |
Properties
| Appearance | Brownish-red Crystalline Powder |
| Application | Antibiotics, Antitubercular; enzyme inhibitors; leprostatic agents; nucleic acid synthesis inhibitors |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 1004.42°C at 760 mmHg |
| Melting Point | >180°C (dec.) |
| Flash Point | 561.3±34.3 °C |
| Density | 1.34 g/cm3 |
| Solubility | Soluble in Chloroform, DMSO, Methanol |
| LogP | 2.7 |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Rifampin acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. |
| Toxicity | LD50: 1570 mg/kg (Rat). |
Reference Reading
1.Epidemiological Trends of Drug-Resistant Tuberculosis in China From 2007 to 2014: A Retrospective Study.
He XC1, Zhang XX, Zhao JN, Liu Y, Yu CB, Yang GR, Li HC. Medicine (Baltimore). 2016 Apr;95(15):e3336. doi: 10.1097/MD.0000000000003336.
The emergence and spread of drug-resistant tuberculosis (DR-TB) has become the major concern in global TB control nowadays due to its limited therapy options and high mortality. A comprehensive evaluation for the epidemiological trends of DR-TB in mainland China, of which TB incidences remain high, is essential but lacking. This study aimed to describe the trends of DR-TB overtime, especially multidrug-resistant TB (MDR-TB); and to identify unique characteristics of MDR-TB cases compared with drug-susceptible TB cases in Mainland China.We retrospectively analyzed surveillance data collected from 36 TB prevention and control institutions in Shandong Province, China over an 8-year period. Unique characteristics of MDR-TB were identified; Chi-square test for trends and linear regression were used to assess the changes in proportions of different resistance patterns overtime.The overall MDR rate was 6.2% in our sample population. There were no statistically significant changes in the percentage of drug-susceptible, isoniazid (INH) resistance, ethambutol (EMB) resistance, streptomycin (SM) resistance, and MDR TB during our study period except that the overall rifampin (RFP) resistance and rifampin monoresistance (RMR) increased at a yearly rate of 0.
2.Rifampin phosphotransferase is an unusual antibiotic resistance kinase.
Stogios PJ1, Cox G2, Spanogiannopoulos P2, Pillon MC3, Waglechner N2, Skarina T2, Koteva K2, Guarné A3, Savchenko A1, Wright GD2. Nat Commun. 2016 Apr 22;7:11343. doi: 10.1038/ncomms11343.
Rifampin (RIF) phosphotransferase (RPH) confers antibiotic resistance by conversion of RIF and ATP, to inactive phospho-RIF, AMP and Pi. Here we present the crystal structure of RPH from Listeria monocytogenes (RPH-Lm), which reveals that the enzyme is comprised of three domains: two substrate-binding domains (ATP-grasp and RIF-binding domains); and a smaller phosphate-carrying His swivel domain. Using solution small-angle X-ray scattering and mutagenesis, we reveal a mechanism where the swivel domain transits between the spatially distinct substrate-binding sites during catalysis. RPHs are previously uncharacterized dikinases that are widespread in environmental and pathogenic bacteria. These enzymes are members of a large unexplored group of bacterial enzymes with substrate affinities that have yet to be fully explored. Such an enzymatically complex mechanism of antibiotic resistance augments the spectrum of strategies used by bacteria to evade antimicrobial compounds.
3.A randomized, comparative study of dual therapy (doxycycline-rifampin) versus triple therapy (doxycycline-rifampin-levofloxacin) for treating
Hasanain A1, Mahdy R2, Mohamed A3, Ali M4. Braz J Infect Dis. 2016 Apr 14. pii: S1413-8670(16)30046-0. doi: 10.1016/j.bjid.2016.02.004. [Epub ahead of print]
AIM: The aim of this study was to compare both the efficacy and safety profile of the WHO-recommended, dual therapy (doxycycline-rifampin) to a quinolone-based, triple therapy (doxycycline-rifampin-levofloxacin) for treating acute/subacute brucellosis.
4.[Gene typing and antibiotic resistance of methicillin-resistant Staphylococcus aureus isolated from lower respiratory tract at two hospitals in Shanghai].
Wang R1, Wan HY, Shi GC, Li M, Han LZ, Jin XY, Sun Q, He P, Zhou M. Zhonghua Jie He He Hu Xi Za Zhi. 2016 Apr 12;39(4):286-90. doi: 10.3760/cma.j.issn.1001-0939.2016.04.007.
OBJECTIVE: To study the genotyping characteristics and antibiotic resistance of methicillin-resistant Staphylococcus aureus(MRSA) isolated from lower respiratory tract at 2 different level hospitals in Shanghai.
Spectrum
Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C43H58N4O12
Molecular Weight (Monoisotopic Mass): 822.4051 Da
Molecular Weight (Avergae Mass): 822.9402 Da
Derivative Type: TMS_1_1
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C43H58N4O12
Molecular Weight (Monoisotopic Mass): 822.4051 Da
Molecular Weight (Avergae Mass): 822.9402 Da
Derivative Type: TMS_1_1
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C43H58N4O12
Molecular Weight (Monoisotopic Mass): 822.4051 Da
Molecular Weight (Avergae Mass): 822.9402 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C43H58N4O12
Molecular Weight (Monoisotopic Mass): 822.4051 Da
Molecular Weight (Avergae Mass): 822.9402 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
