Olivanic acid
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| Category | Antibiotics |
| Catalog number | BBF-03724 |
| CAS | 64761-66-6 |
| Molecular Weight | 270.31 |
| Molecular Formula | C11H14N2O4S |
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Description
Olivanic acid is a β-lactam antibiotic produced by Str. olivaceus. It has anti-gram-positive bacteria and gram-negative bacteria activity, and has the effect of inhibiting β-lactamase.
Specification
| Synonyms | Olivanicacid |
| IUPAC Name | 3-[(E)-2-aminoethenyl]sulfanyl-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| Canonical SMILES | CC(C1C2CC(=C(N2C1=O)C(=O)O)SC=CN)O |
| InChI | InChI=1S/C11H14N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h2-3,5-6,8,14H,4,12H2,1H3,(H,16,17)/b3-2+ |
| InChI Key | HFTVKHFILHLXJF-NSCUHMNNSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Evolution of beta-lactamase inhibitors
G N Rolinson Rev Infect Dis. 1991 Jul-Aug;13 Suppl 9:S727-32. doi: 10.1093/clinids/13.supplement_9.s727.
The production of beta-lactamase is the most important mechanism of bacterial resistance to beta-lactam antibiotics. Attempts to find an inhibitor of beta-lactamase were made as early as the 1940s and 1950s but without success. In the early 1950s, it was found that certain semisynthetic penicillins could function as beta-lactamase inhibitors, but none found a clinical place in this capacity. A program of screening microorganisms for the production of naturally occurring inhibitors was begun in 1967. This process led to the discovery of the olivanic acids and clavulanic acid. Clavulanic acid, formulated with amoxicillin and later with ticarcillin, became available for clinical use in 1981. Since the introduction of clavulanic acid, other beta-lactamase inhibitors have been developed, including sulbactam and tazobactam. It remains to be seen whether these will have any advantage over clavulanate for clinical use.
2. Comparative biological properties of some synthetic olivanic acid analogues
M J Basker, R J Boon, S J Box, A G Brown, P Davis, R J Ponsford, R Southgate, S R Spear J Antibiot (Tokyo). 1983 Oct;36(10):1357-71. doi: 10.7164/antibiotics.36.1357.
A series of olivanic acid/thienamycin analogues have been prepared by total synthesis. Particular attention was given to the effect of the side-chain substituents on the chemical, beta-lactamase and metabolic stability of the final products. All of the compounds possessed a broad and high level of in vitro antibacterial activity against Gram-positive and Gram-negative organisms including beta-lactamase-producing strains. Two derivatives (8c) and (8j) were selected for further evaluation on the basis of in vitro activity, ease of synthesis and stability parameters. The improved metabolic stability of the selected analogues, relative to the naturally-occurring olivanic acid, MM 13902, could be demonstrated in terms of better activity, higher blood levels and improved urinary recovery in in vivo studies in mice.
3. Properties of MM 13902 and other carbapenem antibiotics in vitro and in vivo
M J Basker, R J Boon, S J Box, E A Prestige, G M Smith, S R Spear J Antibiot (Tokyo). 1983 Apr;36(4):416-22. doi: 10.7164/antibiotics.36.416.
The carbapenem antibiotics, which include the olivanic acids and the thienamycins, have a broad-spectrum of antibacterial activity but only thienamycin itself shows appreciable activity against Pseudomonas aeruginosa. The zwitterionic nature of thienamycin was reproduced in the olivanic acid series by preparing the deacetyl derivatives of MM 17880 and MM 22380--compounds NA 26975 and NA 26978. The latter derivative showed antipseudomonas activity and had an antibacterial spectrum similar to thienamycin itself. In contrast the O-sulfated analogue, NA 26975, was no more active than the parent compound against P. aeruginosa. Both deacetyl compounds were more stable than the parent natural products to a mouse kidney enzyme preparation and gave higher urinary recoveries in the mouse. Pharmacokinetic studies with MM 13902 in various animal species showed that the compound was rapidly eliminated from the blood and gave only low urinary recoveries. Similar findings were observed also in human volunteers given MM 13902. The nephrotoxicity reported for thienamycin/MK 0787 in the rabbit was not seen with the olivanic acids MM 13902, MM 17880, MM 22382 and MM 22383 when tested under the same conditions.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
