Coumamidine γ1
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| Category | Antibiotics |
| Catalog number | BBF-01069 |
| CAS | 121634-35-3 |
| Molecular Weight | 835.82 |
| Molecular Formula | C33H49N13O13 |
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Description
It is produced by the strain of Saccharopolyspora sp. AB 1167L-65. It is a kind of alkaline water-soluble sugar Cinodine antibiotic, which has broad spectrum antibacterial activity and also has effect on pseudomonas aeruginosa.
Specification
| Synonyms | Coumamidine gamma1; Coumamidine gamma(1) |
| IUPAC Name | 6-[6-[[6-[4-[(E)-3-[(3-amino-3-iminopropyl)amino]-3-oxoprop-1-enyl]phenoxy]-5-(diaminomethylideneamino)-4-hydroxy-2-methyloxan-3-yl]carbamoylamino]-5-(carbamoylamino)-4-hydroxyoxan-3-yl]oxy-7-hydroxy-2-oxo-3,3a,5,6,7,7a-hexahydropyrano[2,3-d]imidazole-1-carboxamide |
| Canonical SMILES | CC1C(C(C(C(O1)OC2=CC=C(C=C2)C=CC(=O)NCCC(=N)N)N=C(N)N)O)NC(=O)NC3C(C(C(CO3)OC4COC5C(C4O)N(C(=O)N5)C(=O)N)O)NC(=O)N |
| InChI | InChI=1S/C33H49N13O13/c1-12-19(25(50)21(41-29(36)37)28(57-12)58-14-5-2-13(3-6-14)4-7-18(47)40-9-8-17(34)35)43-32(53)44-26-20(42-30(38)51)23(48)15(10-55-26)59-16-11-56-27-22(24(16)49)46(31(39)52)33(54)45-27/h2-7,12,15-16,19-28,48-50H,8-11H2,1H3,(H3,34,35)(H2,39,52)(H,40,47)(H,45,54)(H4,36,37,41)(H3,38,42,51)(H2,43,44,53)/b7-4+ |
| InChI Key | RALPRAPANVNIPH-QPJJXVBHSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.86 g/cm3 |
| Solubility | Soluble in Ethanol, Water, DMSO |
Reference Reading
1. Coumamidines, new broad spectrum antibiotics of the cinodine type. III. Microbiologic activity of coumamidine gamma 1
P B Fernandes, R N Swanson, D J Hardy, C W Hanson, D McDaniel, J Beyer, R H Chen J Antibiot (Tokyo). 1989 Apr;42(4):538-41. doi: 10.7164/antibiotics.42.538.
The coumamidines are novel antibiotics with activity against a wide spectrum of aerobic Gram-positive and Gram-negative bacteria. All microbiological studies were performed on coumamidine gamma 1. The MIC90s (micrograms/ml) of coumamidine are as follows: Staphylococcus aureus 1.0, Streptococcus pyogenes 8, Enterobacteriaceae 2.0, Pseudomonas aeruginosa 8, Campylobacter jejuni and Campylobacter coli 1, Legionella pneumophila 8, Haemophilus influenzae 0.5, Neisseria gonorrhoeae 0.5. Coumamidine had MICs ranging from 8 to greater 0.5, Neisseria gonorrhoeae 0.5. Coumamidine had MICs ranging from 8 to greater than 64 for most anaerobes, except some Peptostreptococcus strains. The aminoglycoside super-sensitive strain, P. aeruginosa BMH 10, was also super-sensitive to coumamidine (MIC 0.2 micrograms/ml). Coumamidine was rapidly bactericidal for S. aureus. The viable bacterial count in logarithmic phase cultures was reduced to less than 10 cfu within 2 hours after exposure to 4 times the MIC (3.12 micrograms/ml) of coumamidine. The frequency of resistance development was less than 1 X 10(-9) for Escherichia coli and S. aureus when selected at 4 and 8 times the MIC. The Cmax in mouse serum after a single subcutaneous dose of 25 mg/kg of coumamidine was 4.5 micrograms/ml and t1/2 was 1 hour. Coumamidine is stable in serum. In mouse protection tests against S. aureus NCTC 10649 the ED50 was less than 0.6 mg/kg/day when it was administered subcutaneously at 1 and 5 hours after infection. Coumamidine was not absorbed after oral administration. The antibacterial spectrum, bactericidal activity, stability in serum and low frequency of resistance make this an interesting new class of antibiotics.
2. Coumamidines, new broad spectrum antibiotics of the cinodine type. II. Isolation and structural elucidation
R H Chen, D N Whittern, A M Buko, J B McAlpine J Antibiot (Tokyo). 1989 Apr;42(4):533-7. doi: 10.7164/antibiotics.42.533.
Two novel, isomeric compounds, coumamidines gamma 1 and gamma 2, were isolated from fermentations of an actinomycete. The structures were elucidated spectroscopically using 2D NMR correlation experiments and mass spectral data. The coumamidines were found to be close structural relatives of the cinodines (LL-BM123 gamma 1 and gamma 2).
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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 ╳
