Basic information
- CAS
6998-60-3- 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- Molecular formula
- C37H47NO12
- Average molar mass
- 697.8 g/mol
- Monoisotopic mass
- 697.30982594
Overview
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-).
Names & identifiers
- Preferred 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
- English name
- RIFAMYCIN SV
- Molecular formula
- C37H47NO12
- Molecular weight
- 697.77
Names & synonyms
RIFAMYCINRifamycin SVRifamicine SVRifomycin SVRifamicinaRifamycineRifamycinum6998-60-3RifocynRIFOMYCINDU69T8ZZPADTXSID1032014
Show more names
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
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 201 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 3
- Heavy atoms
- 50
- Formal charge
- 0
- Complexity
- 1,330
Experimental & physicochemical properties
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
Physicochemical properties
- Melting point
- 300 ° · 300° (dec 140°)
- alpha
- 20 · D20 -4° (methanol)
- Boiling point
- 701.9 °C · 701.9°C (rough estimate)
- Density
- 1.2275 · 1.2275 (rough estimate)
- refractive index
- 1.535 · 1.5350 (estimate)
- pka
- 5.17 · 5.17±0.70(Predicted)
- FDA UNII
- 69 T8ZZPA · DU69T8ZZPA
Safety & regulation
Hazard information
Other Safety InformationIMAP assessments - Rifamycin: Environment tier I assessment
Toxicology
Hepatotoxicity
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
Safety data
- Toxicity
- LD50 in mice (mg/kg): 550 i.v.; 625 i.p.; 2120 orally (Bergamini, Fowst)
Chemistry & industry
Pharmacology
ATC Code
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
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
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.
Related reactions
4 records
Compound notes
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