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Rifamycin (sodium)

CAT: 0804-HY-B1907-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B1907-01Size:50 mg
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Description
Rifamycin sodium (Rifamycin SV monosodium) is an orally active ansamycin antibiotic. Rifamycin sodium inhibits DNA-dependent RNA synthesis. Rifamycin sodium has antibacterial activity against Mycobacterium tuberculosis. Rifamycin sodium interferes with hepatic bile acid metabolism. Rifamycin sodium has anti-inflammatory effects. Rifamycin sodium can be used in the study of Mycobacterium tuberculosis, Bacteroides fragilis infection, and Lipopolysaccharide -induced inflammation[1][2][3][4][5][6][7][8][9][10][11].
CAS Number
14897-39-3
Product Name Alternative
Rifamycin SV (sodium)
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Antibiotic; Bacterial; DNA/RNA Synthesis
Type
Natural Products
Related Pathways
Anti-infection; Cell Cycle/DNA Damage
Applications
COVID-19-immunoregulation
Field of Research
Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/rifamycin-sodium.html
Purity
99.56
Solubility
DMSO : 175 mg/mL (ultrasonic)
Smiles
O=C1C2=C(C([O-])=CC(NC(/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@H]3C)=O)=C4O)C4=C(O)C(C)=C2O[C@@]1(O/C=C/[C@@H]([C@H]([C@@]3([H])OC(C)=O)C)OC)C.[Na+]
Molecular Formula
C37H46NNaO12
Molecular Weight
719.75
Precautions
H302, H315, H319, H335
References & Citations
[1]Floss HG, et al. Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105 (2) :621-32.|[2]Fattinger K, et al. Rifamycin SV and rifampicin exhibit differential inhibition of the hepatic rat organic anion transporting polypeptides, Oatp1 and Oatp2. Hepatology. 2000 Jul;32 (1) :82-6.|[3]Rosette C, et al. Anti-inflammatory and immunomodulatory activities of rifamycin SV. Int J Antimicrob Agents. 2013 Aug;42 (2) :182-6. |[4]Tsukamura M, et al. Antituberculous Action of Rifamycin SV* In Vitro and In Vivo Studies. The Journal of Antibiotics, Series A, 1962, 15 (5) : 216-224.|[5]Saito K, et al. Rifamycin action on RNA polymerase in antibiotic-tolerant Mycobacterium tuberculosis results in differentially detectable populations. Proc Natl Acad Sci U S A. 2017 Jun 13;114 (24) :E4832-E4840.|[6]Jallouli M, et al. Rifamycin lavage in the treatment of experimental intra-abdominal infection. J Surg Res. 2009 Aug;155 (2) :191-4.|[7]Zhang M, et al. Treatment of tuberculosis with rifamycin-containing regimens in immune-deficient mice. Am J Respir Crit Care Med. 2011 May 1;183 (9) :1254-61.|[8]Omansen TF, et al. High-Dose Rifamycins Enable Shorter Oral Treatment in a Murine Model of Mycobacterium ulcerans Disease. Antimicrob Agents Chemother. 2019 Jan 29;63 (2) :e01478-18.|[9]Özbay C, et al. Ototoxic effect of topical rifamycin SV applied in the middle ear of rats. The Turkish Journal of Ear Nose and Throat, 2017, 27 (1) : 31-38.|[10]Okolicsanyi L, et al. Influence of rifamycin SV on bile acid metabolism in rats. Naunyn Schmiedebergs Arch Pharmacol. 1980 Aug;313 (2) :171-4.|[11]Dijkmans B A C, et al. Efficacy of rifamycin SV and vancomycin against Bacteroides fragilis in vitro and in experimentally infected mice. Current Microbiology, 1985, 12: 53-58.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture)
Scientific Category
Natural Products
Clinical Information
Launched

Chemical Information

Rifamycin Sodium

Rifamycin Sodium is a sodium salt of rifamycin, an antibiotic produced by Streptomyces mediterranei which is used to treat mycobacterium infections.

CAS Number14897-39-3
PubChem CID23702994
IUPAC Namesodium (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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(29),2,4,9,19,21,25,27-octaen-27-olate
Molecular FormulaC37H46NNaO12
Molecular Weight719.7
Topological Polar Surface Area204
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Heavy Atom Count51
Formal Charge0
Complexity1340
SMILES
C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)[O-])/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-NLYBMVFSSA-M
Chemical Structure
2D Structure
2D structure of Rifamycin Sodium
CAS: 14897-39-3
CID: 23702994
Formula: C37H46NNaO12
MW: 719.7
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight719.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Exact Mass719.29177018
Monoisotopic Mass719.29177018
Topological Polar Surface Area204 Ų
Heavy Atom Count51
Formal Charge0
Complexity1340
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes