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6998-60-3

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6998-60-3 Usage

Uses

Rifogal (Rifaximin EP Impurity C NA) is a antibacterial drug which functions by inhibiting bacterial RNA polymerase (RNAP), is an important part of the antibacteral armamentarium. Also, it is one of the few drugs in a multidrug regimens for treating lung disease (LD) due to Mycobacterium avium complex (MAC).

Definition

ChEBI: A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.

Pharmaceutical Applications

The simplest rifamycin in clinical use, obtained by elimination of a glycolic moiety from rifamycin B. Formulated as sodium salt for parenteral administration. Also available for topical use. Its activity, general properties and pharmacokinetics are very similar to those of rifamide. It is orally absorbed and excreted mainly in the bile. Intramuscular doses of 250 mg produce mean plasma levels of about 2 mg/L. The plasma half-life is around 2 h.In addition to uses similar to those of rifamide, it is administered topically in surgery and has been proposed for the treatment of synovitis by intra-articular injections. A topical preparation is used for application to wounds and bedsores. Cases of anaphylactic reactions have been reported after local administration of the drug.

Purification Methods

Rifamycin SV gives yellow-orange crystals from Et2O/pet ether or aqueous EtOH, is very soluble in MeOH, EtOH, Me2CO and EtOAc, and is less soluble in Et2O and HCO3-, but slightly soluble in H2O and pet ether. Its UV has max at 223, 314 and 445nm ( 1cm 586, 322 and 204) in phosphatebuffer pH 7. [NMR: Bergamini & Fowst Arzneim.-Forsch 15 951 1965.]

Check Digit Verification of cas no

The CAS Registry Mumber 6998-60-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,9 and 8 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6998-60:
(6*6)+(5*9)+(4*9)+(3*8)+(2*6)+(1*0)=153
153 % 10 = 3
So 6998-60-3 is a valid CAS Registry Number.
InChI:InChI=1/C37H47NO12/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)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1

6998-60-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name rifamycin SV

1.2 Other means of identification

Product number -
Other names RIFAMYCIN SV

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6998-60-3 SDS

6998-60-3Synthetic route

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 0.25h; Ambient temperature;
Conditions
ConditionsYield
With hydrogenchloride; indium In tetrahydrofuran; water
rifamycin SV
6998-60-3

rifamycin SV

4,11-dideoxy-4,11-dihydroxyiminorifamycin S

4,11-dideoxy-4,11-dihydroxyiminorifamycin S

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In methanol85%
N,N-dihydroxymethyltert-butylamine
55686-22-1

N,N-dihydroxymethyltert-butylamine

rifamycin SV
6998-60-3

rifamycin SV

N-tert-1,3-oxazine(5,6-c)rifamycin

N-tert-1,3-oxazine(5,6-c)rifamycin

Conditions
ConditionsYield
With acetic acid In N,N-dimethyl-formamide at 55℃; for 1.5h; Temperature; Molecular sieve; Large scale;84.55%
Conditions
ConditionsYield
With potassium hexacyanoferrate(III) In pyridine
With oxygen; magnesium chloride In water
Conditions
ConditionsYield
With potassium hexacyanoferrate(III)
rifamycin SV
6998-60-3

rifamycin SV

3-Bromrifamycin S
57375-25-4

3-Bromrifamycin S

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide In ethanol
rifamycin SV
6998-60-3

rifamycin SV

3-amino-O1,O4-didehydro-rifamycin
51756-80-0

3-amino-O1,O4-didehydro-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K3Fe(CN)6 / pyridine
2: NH3 / dioxane
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

3-Chlorrifamycin S
57375-24-3

3-Chlorrifamycin S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridinium bromide perbromide / ethanol
2: LiCl / acetone
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

3-cyano-O1,O4-didehydro-rifamycin
57375-26-5

3-cyano-O1,O4-didehydro-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K3Fe(CN)6 / pyridine
2: NH4Cl / dimethylformamide
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

3-cyano-rifamycin
61169-31-1

3-cyano-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K3Fe(CN)6 / pyridine
2: NH4Cl / dimethylformamide
3: ascorbic acid / methanol; H2O
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

3-tert-butylsulfanyl-O1,O4-didehydro-rifamycin
57375-29-8

3-tert-butylsulfanyl-O1,O4-didehydro-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K3Fe(CN)6 / pyridine
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

3-(4'-Phenylbutylamino)rifamycin SV
61169-32-2

3-(4'-Phenylbutylamino)rifamycin SV

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K3Fe(CN)6 / pyridine
3: ascorbic acid / methanol; H2O
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

3-(4-phenyl-butylamino)-O1,O4-didehydro-rifamycin
57375-28-7

3-(4-phenyl-butylamino)-O1,O4-didehydro-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K3Fe(CN)6 / pyridine
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

Rifamycin B
13929-35-6

Rifamycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: magnesium chloride; oxygen / water
2: transketolase Rif15; cytochrome P450 enzyme Rif16; thiamine pyrophosphate; magnesium chloride / aq. buffer / 4 h / 28 °C / pH 7.4 / Enzymatic reaction
3: ferredoxin seFdx; ferredoxin reductasese FdR; NADPH; cytochrome P450 enzyme Rif16 / aq. buffer / 4 h / 28 °C / Enzymatic reaction
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

[39-13C]-rifamycin L

[39-13C]-rifamycin L

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; oxygen / water
2: ATP; hexokinase; phosphoglucose isomerase; transketolase Rif15; thiamine pyrophosphate; magnesium chloride / 16 h / 28 °C / Enzymatic reaction
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

C38(13)CH49NO14

C38(13)CH49NO14

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: magnesium chloride; oxygen / water
2: ATP; hexokinase; phosphoglucose isomerase; transketolase Rif15; thiamine pyrophosphate; magnesium chloride / 16 h / 28 °C / Enzymatic reaction
3: ferredoxin seFdx; ferredoxin reductasese FdR; NADPH; cytochrome P450 enzyme Rif16 / 16 h / 28 °C / Enzymatic reaction
View Scheme
rifamycin SV
6998-60-3

rifamycin SV

rifamycin L

rifamycin L

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; oxygen / water
2: transketolase Rif15; cytochrome P450 enzyme Rif16; thiamine pyrophosphate; magnesium chloride / aq. buffer / 4 h / 28 °C / pH 7.4 / Enzymatic reaction
View Scheme

6998-60-3Relevant articles and documents

3-(SUBSTITUTED ETHYL)-RIFAMYCIN DERIVATIVES USEFUL AS ANTIMICROBIAL AGENTS

-

Page/Page column 15, (2010/03/02)

The present invention is directed to novel 3-(substituted ethyl) rifamycin derivatives, pharmaceutical compositions containing them and the use of said derivatives and pharmaceutical compositions as antimicrobial agents against pathogenic microorganisms, particularly against resistant microbes.

Process for preparing rifamycin derivatives

-

, (2008/06/13)

3-Dialkylaminomethyl derivatives of rifamycin S is provided by reacting rifamycin S with an iminium salt in an organic solvent. This compound is converted to 3-dialkylaminomethyl derivatives by virtue of ascorbic acid.

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