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MedKoo Cat#: 466173 | Name: BMS-181184

Description:

WARNING: This product is for research use only, not for human or veterinary use.

BMS-181184 is a novel antifungal and fungicidal agent.

Chemical Structure

BMS-181184
BMS-181184
CAS#139272-69-8

Theoretical Analysis

MedKoo Cat#: 466173

Name: BMS-181184

CAS#: 139272-69-8

Chemical Formula: C39H41NO20

Exact Mass: 843.2222

Molecular Weight: 843.74

Elemental Analysis: C, 55.52; H, 4.90; N, 1.66; O, 37.92

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
BMS-181184; BMS181184; BMS 181184; 3'-Hydroxybenanomicin A; 3' Hydroxybenanomicin A;
IUPAC/Chemical Name
((5S,6S)-5-(((2S,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5,6,8,13-tetrahydrobenzo[a]tetracene-2-carbonyl)-D-serine
InChi Key
AXPBRQZJFXIYTD-XCXKMOQISA-N
InChi Code
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+/m1/s1
SMILES Code
O=C(O)[C@H](NC(C1=C(C)C=C2[C@H](O[C@@H]3O[C@H](C)[C@H](O)[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)[C@@H](O)C5=CC6=C(C(C7=CC(OC)=CC(O)=C7C6=O)=O)C(O)=C5C2=C1O)=O)CO
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 843.74 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Oakley KL, Moore CB, Denning DW. Activity of pradimicin BMS-181184 against Aspergillus spp. Int J Antimicrob Agents. 1999 Aug;12(3):267-9. doi: 10.1016/s0924-8579(99)00072-2. PMID: 10461847. 2: Restrepo MI, Najvar LK, Fothergill AW, Graybill JR. Pradimicin therapy of disseminated Candida tropicalis infection in the mouse. Med Mycol. 1998 Jun;36(3):181-4. PMID: 9776832. 3: Groll AH, Sein T, Petraitis V, Petraitiene R, Callender D, Gonzalez CE, Giri N, Bacher J, Piscitelli S, Walsh TJ. Compartmental pharmacokinetics and tissue drug distribution of the pradimicin derivative BMS 181184 in rabbits. Antimicrob Agents Chemother. 1998 Oct;42(10):2700-5. doi: 10.1128/AAC.42.10.2700. PMID: 9756780; PMCID: PMC105922. 4: Gonzalez CE, Groll AH, Giri N, Shetty D, Al-Mohsen I, Sein T, Feuerstein E, Bacher J, Piscitelli S, Walsh TJ. Antifungal activity of the pradimicin derivative BMS 181184 in the treatment of experimental pulmonary aspergillosis in persistently neutropenic rabbits. Antimicrob Agents Chemother. 1998 Sep;42(9):2399-404. doi: 10.1128/AAC.42.9.2399. PMID: 9736570; PMCID: PMC105840. 5: Karlowsky JA, Zhanel GG, Balko TV, Zelenitsky SA, Kabani AM, Hoban DJ. In vitro antifungal activity of BMS-181184 against systemic isolates of Candida, Cryptococcus, and Blastomyces species. Diagn Microbiol Infect Dis. 1997 Aug;28(4):179-82. doi: 10.1016/s0732-8893(97)00061-8. PMID: 9327245. 6: Fung-Tomc JC, Bonner DP. Recent developments in pradimicin-benanomicin and triazole antibiotics. Expert Opin Investig Drugs. 1997 Feb;6(2):129-45. doi: 10.1517/13543784.6.2.129. PMID: 15989596. 7: Walsh TJ, Giri N. Pradimicins: a novel class of broad-spectrum antifungal compounds. Eur J Clin Microbiol Infect Dis. 1997 Jan;16(1):93-7. doi: 10.1007/BF01575126. PMID: 9063679. 8: Wardle HM, Law D, Denning DW. In vitro activity of BMS-181184 compared with those of fluconazole and amphotericin B against various candida spp. Antimicrob Agents Chemother. 1996 Sep;40(9):2229-31. doi: 10.1128/AAC.40.9.2229. PMID: 8878616; PMCID: PMC163508. 9: Fung-Tomc JC, Minassian B, Huczko E, Kolek B, Bonner DP, Kessler RE. In vitro antifungal and fungicidal spectra of a new pradimicin derivative, BMS-181184. Antimicrob Agents Chemother. 1995 Feb;39(2):295-300. doi: 10.1128/AAC.39.2.295. PMID: 7726485; PMCID: PMC162530. 10: Furumai T, Saitoh K, Kakushima M, Yamamoto S, Suzuki K, Ikeda C, Kobaru S, Hatori M, Oki T. BMS-181184, a new pradimicin derivative. Screening, taxonomy, directed biosynthesis, isolation and characterization. J Antibiot (Tokyo). 1993 Feb;46(2):265-74. doi: 10.7164/antibiotics.46.265. PMID: 8468241. 11: Ueki T, Numata K, Sawada Y, Nakajima T, Fukagawa Y, Oki T. Studies on the mode of antifungal action of pradimicin antibiotics. I. Lectin-mimic binding of BMY-28864 to yeast mannan in the presence of calcium. J Antibiot (Tokyo). 1993 Jan;46(1):149-61. doi: 10.7164/antibiotics.46.149. PMID: 8436548. 12: Oki T, Kakushima M, Hirano M, Takahashi A, Ohta A, Masuyoshi S, Hatori M, Kamei H. In vitro and in vivo antifungal activities of BMS-181184. J Antibiot (Tokyo). 1992 Sep;45(9):1512-7. doi: 10.7164/antibiotics.45.1512. PMID: 1429237. 13: Kondo S, Gomi S, Uotani K, Miyakawa S, Inouye S, Ikeda D, Takeuchi T. New hydroxybenanomicins produced by Actinomadura. Drugs Exp Clin Res. 1992;18(6):217-24. PMID: 1478160.