Rifamycin

HCID 6324616CAS 6998-60-3

Grundinformationen

Standard-SMILES
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)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
InChIKey
HJYYPODYNSCCOU-ODRIEIDWSA-N
Summenformel
C37H47NO12
Durchschnittliche Molmasse
697,8 g/mol
Monoisotopische Masse
697,30982594

Überblick

Rifamycin SV is a member of the class of rifamycins that exhibits antibiotic and antitubercular properties. It has a role as an antitubercular agent, an antimicrobial agent and a bacterial metabolite. It is a lactam, a polyphenol, a member of rifamycins, an organic heterotetracyclic compound, an acetate ester, a macrocycle and a cyclic ketal. It is a conjugate acid of a rifamycin SV(1-).

Namen und Bezeichner

Bevorzugter Name
Rifamycin
IUPAC
[(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-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
Lokaler Name
Rifamycin
Englischer Name
RIFAMYCIN SV
Summenformel
C37H47NO12
Molmasse
697.77

Namen und Synonyme

RIFAMYCINRifamycin SVRifamicine SVRifomycin SVRifamicinaRifamycineRifamycinum6998-60-3RifocynRIFOMYCINDU69T8ZZPADTXSID1032014
Weitere Namen anzeigen
rifocinrifamicinesvRIFAMYCIN INNRifamycin S-NaRifamycin (9CI)RIFAMYCIN SV USP/EP/BPRifaximin EP Impurity CRifaximin impurity C (EP)
[(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-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] acetateCHEBI:29673Rifamycin SV, an antibiotic produced by certain strains of Streptomyces mediterranei, or the same substance produced by any other meansRifamycine Chibret5,6,9,17,19,21-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 21-acetate((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-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(7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-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^(5,28))triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate(7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-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^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate

Datenbank-Bezeichner

CAS
6998-60-3
PubChem CID
6324616
DTXSID
DTXSID1032014
ChEMBL
CHEMBL437765
ChEBI
CHEBI:29673
UNII
DU69T8ZZPA
EC Number
230-273-3

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,9
Polarare Oberfläche (TPSA)
201 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
12
Frei drehbare Bindungen
3
Schwere Atome
50

Experimentelle und physikochemische Eigenschaften

LipidsPolyketides [PK] -> Ansamycins and related polyketides [PK05]
SolubilityInsoluble
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Gastrointestinal Agents; Rifamycins
Endocrine DisruptorsPotential endocrine disrupting compound
Dissociation Constants1.8

Physikochemische Eigenschaften

Schmelzpunkt
300 ° · 300° (dec 140°)
Siedepunkt
701.9 °C · 701.9°C (rough estimate)
Dichte
1.2275 · 1.2275 (rough estimate)
Brechungsindex
1.535 · 1.5350 (estimate)
pka
5.17 · 5.17±0.70(Predicted)

Sicherheit und Regulatorisches

Gefahrenhinweise

Other Safety InformationIMAP assessments - Rifamycin: Environment tier I assessment

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

In prelicensure controlled trials in patients with traveler’s diarrhea, rates of serum ALT elevations were similar in subjects treated with rifamycin compared to placebo or comparator agent (ciprofloxacin) and no participants developed clinically apparent liver injury. Since its approval, there have been no published reports of hepatotoxicity attributed to rifamycin. Because of its minimal absorption rifamycin is considered unlikely to cause liver injury.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Toxizität
LD50 in mice (mg/kg): 550 i.v.; 625 i.p.; 2120 orally (Bergamini, Fowst)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 6 Einträge

J04AB03

A - Alimentary tract and metabolism

S - Sensory organs

S - Sensory organs

J - Antiinfectives for systemic use

D - Dermatologicals

Protein BindingThe protein binding of rifamycin is of about 80-95%.
Pharmacodynamics · 1 Eintrag

Rifamycin is known to be effective against Gram-positive and Gram-negative pathogens and mycobacteria. It is very effective against _E. coli_ reporting a MIC90 of 64-128 mcg/ml without showing cross-resistance with other antimicrobial agents. The specific indication of rifamycin is extremely important as ther were previous reports that indicated a high risk factor in the generation of resistant _E. coli_ strains in patients with inflammatory bowel disease. In clinical trials, rifamycin was tested in a randomized clinical trial of travellers' coming from Mexico and Guatemala. In this trial, rifamycin was proven to significantly reduce the symptoms of travellers' diarrhea.

Mechanism of Action · 1 Eintrag

Rifamycins, as well as all the other members of this group, present an antibacterial mechanism of action related to the inhibition of RNA synthesis. This mechanism of action is done by the strong binding to the DNA-dependent RNA polymerase of prokaryotes. The inhibition of the RNA synthesis is thought to be related with the initiation phase of the process and to involve stacking interactions between the naphthalene ring and the aromatic moiety in the polymerase. As well, it has been suggested that the presence of zinc atoms in the polymerase allows for the binding of phenolic -OH groups of the naphthalene ring. In eukaryotic cells, the binding is significantly reduced making them at least 100 to 10,000 times less sensitive to the action of rifamycins. The members of the rifamycin family present the same mechanism of action and the structural modifications are usually related to pharmacokinetic properties as well as to the interaction with eukaryotic cells.

Biological Half-LifeThe reported half-life when a dose of 250 mg of rifamycin was administered is 3 h.
Metabolism/MetabolitesWhen absorbed, rifamycin is mainly metabolzied in hepatocytes and intestinal microsomes to a 25-deacetyl metabolite.
Anwendungen · 1 Eintrag

VerwendenRifogal (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).

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Anbieter50 Anbieter

江苏艾康生物医药研发有限公司025-58851090 19370895928 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]

Ergänzende Hinweise

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

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