BMS-181184
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03251 |
| CAS | 139272-69-8 |
| Molecular Weight | 843.74 |
| Molecular Formula | C39H41NO20 |
Online Inquiry
Description
BMS-181184 is an antifungal antibiotic produced by Actinomadura sp. AB1236 in a medium containing D-serine or D-cycloserine. It has activity against pathogenic fungi such as yeast, Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus and Trichophyton.
Specification
| Synonyms | D-Serine, N-((5-((6-deoxy-3-O-beta-D-xylopyranosyl-beta-D-galactopyranosyl)oxy)-5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxobenzo(a)naphthacen-2-yl)carbonyl)-, (5S-trans)- |
| IUPAC Name | 2-[[(5S)-5-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carbonyl]amino]-3-hydroxypropanoic acid |
| Canonical SMILES | CC1C(C(C(C(O1)OC2C(C3=CC4=C(C(=C3C5=C2C=C(C(=C5O)C(=O)NC(CO)C(=O)O)C)O)C(=O)C6=C(C4=O)C(=CC(=C6)OC)O)O)O)OC7C(C(C(CO7)O)O)O)O |
| InChI | InChI=1S/C39H41NO20/c1-10-4-16-23(30(49)20(10)36(53)40-17(8-41)37(54)55)22-14(7-15-24(31(22)50)27(46)13-5-12(56-3)6-18(42)21(13)26(15)45)28(47)34(16)59-39-33(52)35(25(44)11(2)58-39)60-38-32(51)29(48)19(43)9-57-38/h4-7,11,17,19,25,28-29,32-35,38-39,41-44,47-52H,8-9H2,1-3H3,(H,40,53)(H,54,55)/t11?,17?,19?,25?,28?,29?,32?,33?,34-,35?,38?,39?/m0/s1 |
| InChI Key | AXPBRQZJFXIYTD-PWEAUJHISA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 218°C(dec.) |
Reference Reading
1. Compartmental pharmacokinetics and tissue drug distribution of the pradimicin derivative BMS 181184 in rabbits
A H Groll, T Sein, V Petraitis, R Petraitiene, D Callender, C E Gonzalez, N Giri, J Bacher, S Piscitelli, T J Walsh Antimicrob Agents Chemother. 1998 Oct;42(10):2700-5. doi: 10.1128/AAC.42.10.2700.
The pharmacokinetics of the antifungal pradimicin derivative BMS 181184 in plasma of normal, catheterized rabbits were characterized after single and multiple daily intravenous administrations of dosages of 10, 25, 50, or 150 mg/kg of body weight, and drug levels in tissues were assessed after multiple dosing. Concentrations of BMS 181184 were determined by a validated high-performance liquid chromatography method, and plasma data were modeled into a two-compartment open model. Across the investigated dosage range, BMS 181184 demonstrated nonlinear, dose-dependent kinetics with enhanced clearance, reciprocal shortening of elimination half-life, and an apparently expanding volume of distribution with increasing dosage. After single-dose administration, the mean peak plasma BMS 181184 concentration (Cmax) ranged from 120 microg/ml at 10 mg/kg to 648 microg/ml at 150 mg/kg; the area under the concentration-time curve from 0 to 24 h (AUC0-24) ranged from 726 to 2,130 microg . h/ml, the volume of distribution ranged from 0.397 to 0.799 liter/kg, and the terminal half-life ranged from 4.99 to 2.31 h, respectively (P < 0.005 to P < 0.001). No drug accumulation in plasma occurred after multiple daily dosing at 10, 25, or 50 mg/kg over 15 days, although mean elimination half-lives were slightly longer. Multiple daily dosing at 150 mg/kg was associated with enhanced total clearance and a significant decrease in AUC0-24 below the values obtained at 50 mg/kg (P < 0.01) and after single-dose administration of the same dosage (P < 0.05). Assessment of tissue BMS 181184 concentrations after multiple dosing over 16 days revealed substantial uptake in the lungs, liver, and spleen and, most notably, dose-dependent accumulation of the drug within the kidneys. These findings are indicative of dose- and time-dependent elimination of BMS 181184 from plasma and renal accumulation of the compound after multiple dosing.
2. Activity of pradimicin BMS-181184 against Aspergillus spp
K L Oakley, C B Moore, D W Denning Int J Antimicrob Agents. 1999 Aug;12(3):267-9. doi: 10.1016/s0924-8579(99)00072-2.
The pradimicins are a new class of antifungal agents with activity against the majority of human fungal pathogens. In this study, the in vitro activity of pradimicin BMS-181184 was investigated against a range of the most common species of Aspergillus. The results were compared with itraconazole and amphotericin B. BMS-181184 was found to be active against most Aspergillus spp., but at higher concentrations than itraconazole and amphotericin B.
3. Antifungal activity of the pradimicin derivative BMS 181184 in the treatment of experimental pulmonary aspergillosis in persistently neutropenic rabbits
C E Gonzalez, A H Groll, N Giri, D Shetty, I Al-Mohsen, T Sein, E Feuerstein, J Bacher, S Piscitelli, T J Walsh Antimicrob Agents Chemother. 1998 Sep;42(9):2399-404. doi: 10.1128/AAC.42.9.2399.
The activity of the pradimicin derivative BMS 181184 was evaluated in a model of invasive pulmonary aspergillosis in persistently neutropenic rabbits and compared with that of amphotericin B deoxycholate. BMS 181184 at total daily doses of 50 and 150 mg/kg of body weight was at least as effective as amphotericin B at 1 mg/kg once a day in conferring survival and had comparable activity in reducing organism-mediated tissue injury and excess lung weight. Although treatment at all dosing regimens of BMS 181184 resulted in significant reductions in fungal tissue burden compared to untreated controls, equivalence to amphotericin B occurred only at the higher dosage level. Similar observations were made in bronchoalveolar lavage fluid cultures obtained postmortem. Monitoring of the animals through ultrafast computerized tomography scan revealed a marked resolution of pulmonary lesions during treatment with BMS 181184. The compound was well tolerated at all dosing regimens, and no toxicity was noted. Pharmacokinetic studies revealed nonlinear drug disposition with increased clearance at higher dosages and some evidence for extravascular drug accumulation. BMS 181184 had excellent activity in the treatment of experimental invasive pulmonary aspergillosis in persistently neutropenic rabbits, thus underscoring the potential of pradimicin derivatives in therapy of invasive aspergillosis in the neutropenic host.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
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 ╳
