ChemicalBook CAS DataBase List 14897-39-3

14897-39-3

Name	Rifamycin Sodium
CAS	14897-39-3
EINECS(EC#)	238-965-7
Molecular Formula	C37H46NNaO12
MDL Number	MFCD00056847
Molecular Weight	719.75
MOL File	14897-39-3.mol

Synonyms

Rifamycin SV s RIFAMYCIN SODIUM Rifamycinsodiumsal RIFAMYCIN SV-SODIUM Rifamycin sodium CRS RIFAMPICIN SV SODIUM rifamycin sodium salt Rifamycin Na USP/EP/BP Rifamycin SV Monosodium RIFAMYCIN,MONOSODIUMSALT RIFAMYCIN SV SODIUM SALT Rifamycin Sodium USP/EP/BP RifaMycin SV MonosodiuM salt RifaMycin, sodiuM salt (1:1) Rifamycin SV sodium, >=900 IU/mg RIFAMYCIN SV SODIUM SALT HEXAHYDRATE Rifamycin SV hexahydrate sodium salt Rifamycin SV Sodium Salt (Rifaximin EP Impurity C Sodium Salt) 5,6,9,17,19,21-Hexahydroxy-23-Methoxy-2,4,12,16,18,20,22-heptaMethyl- 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate, monosodium salt (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-21-(Acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione sodium salt

Chemical Properties

Melting point	>215°C (dec.)
storage temp.	-20°C Freezer
solubility	ethanol: soluble50mg/mL
form	powder
color	Dark Red
Water Solubility	Soluble in water, alcohol and dimethyl sulfoxide.
Merck	13,8302
InChIKey	DJAAUWJRMPPGDA-HSBICLRHNA-N
SMILES	[Na+].CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)cc([O-])c4c3C2=O

Safety Data

Safety Statements	22-24/25 less more
WGK Germany	3
RTECS	KD1922500
F	8-10-23
Storage Class	11 - Combustible Solids

Raw materials And Preparation Products

Hazard Information

Chemical Properties

Dark Red Solid

Uses

Semi-synthetic antibiotic derived from Rifamycin S. Antibacterial. Potency >900 units (dry basis).

Biological Activity

Rifamycin SV inhibits selective (E. coliB. subtilis) bacterial DNA-dependent RNA polymerase by binding to the polymerase β-subunita mechanism similar to rifabutin. It acts as a selective cytochrome P450 3A4 inducer. It is active against Gram-positive bacteria and is moderately active against Gram-negative organisms.

in vivo

Rifamycin (5 mg/day; s.c.; 3 days a week) sodium is effective in mice infected with M. tuberculosis, significantly reducing the number of viable bacteria in the body^[4].
Rifamycin (12.5-25 mg/kg; peritoneal lavage) sodium can improve the survival rate of rats with experimental intraperitoneal infection and significantly reduce the number of intraperitoneal bacteria and adhesion formation^[6].
Rifamycin (5-40 mg/kg; esophageal gavage; once a day, 5 days a week; 4 weeks) sodium shortens oral treatment duration in a mouse model of Mycobacterium ulcerans disease^[8].
Rifamycin (0.1 mL; intraaural administration; twice daily; 10 days) sodium does not cause hearing loss in adult or weanling rats^[9].
Rifamycin (1 mg i.v. bolus followed by 4 mg i.v. infusion; 70 min) sodium interferes with three major steps of Bile acid metabolism in rats with intravenous Sodium cholate (HY-N0324A) infusion, resulting in a significant decrease in bile acid uptake and excretion^[10].
Rifamycin (10-160 mg/kg; s.c.; single dose) sodium is approximately 11 times less effective than Metronidazole (HY-B0318) in a mouse Bacteroides fragilis thigh infection model^[11].

Animal Model:	Male Wistar rats (weight 200-250 g), cecal ligation puncture (CLP)-induced intra-abdominal infection model^[6]
Dosage:	25 mg/kg, 12.5 mg/kg
Administration:	Peritoneal lavage
Result:	Improved survival from 50% in the control group to 91.7% in the 25 mg/kg group and 100% in the 12.5 mg/kg group. Significantly reduced adhesion formation. Showed a greater reduction in bacterial counts in peritoneal fluid (25 mg/kg).

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