Synonym
Propionylmaridomycin; Propionylmaridomycin I;
IUPAC/Chemical Name
(1R,3R,7R,8R,9S,10R,12R,13S,16R,E)-9-(((2R,3S,4S,5R,6R)-4-(dimethylamino)-3-hydroxy-5-(((2S,4S,5S,6S)-4-hydroxy-4,6-dimethyl-5-((3-methylbutanoyl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-8-methoxy-3,12-dimethyl-5-oxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-ene-7,13-diyl dipropionate
InChi Key
YOEZGCFEDPFSHG-IHBICIFHSA-N
InChi Code
InChI=1S/C46H75NO17/c1-13-34(49)60-30-15-16-31-32(59-31)21-26(6)56-37(52)22-33(61-35(50)14-2)43(55-12)42(29(17-18-48)20-25(30)5)64-45-40(53)39(47(10)11)41(27(7)58-45)63-38-23-46(9,54)44(28(8)57-38)62-36(51)19-24(3)4/h15-16,18,24-33,38-45,53-54H,13-14,17,19-23H2,1-12H3/b16-15+/t25-,26-,27-,28+,29+,30-,31-,32-,33-,38+,39+,40+,41+,42+,43-,44+,45-,46+/m1/s1
SMILES Code
C[C@@H]([C@H](OC(CC(C)C)=O)[C@@](C)(O)C1)O[C@H]1O[C@@H]2[C@H]([C@H](O)[C@H](O[C@@H]2C)O[C@@H]3[C@H](OC)[C@H](OC(CC)=O)CC(O[C@H](C)C[C@@H]4[C@H](O4)/C=C/[C@H]([C@H](C)C[C@@H]3CC=O)OC(CC)=O)=O)N(C)C
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
914.09
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.
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: Matsuzawa T, Kondo T, Kita Y. Studies on the absorption, distribution, metabolism, and excretion of propionylmaridomycin in rats. Antimicrob Agents Chemother. 1974 Dec;6(6):685-90. PubMed PMID: 4451342; PubMed Central PMCID: PMC444720.
2: Kondo M, Oishi T, Tsuchiya K, Goto S, Kuwahara S. Maridomycin, a new macrolide antibiotic. In vitro antibacterial activity of 9-propionylmaridomycin. Antimicrob Agents Chemother. 1973 Aug;4(2):149-55. PubMed PMID: 4790935; PubMed Central PMCID: PMC444520.
3: Kondo M, Ishifuji K, Tsuchiya K, Goto S, Kuwahara S. Maridomycin, a new macrolide antibiotic: in vivo antibacterial activity of 9-propionylmaridomycin. Antimicrob Agents Chemother. 1973 Aug;4(2):156-9. PubMed PMID: 4790936; PubMed Central PMCID: PMC444521.
4: Katsu M, Fujimoro I, Shimada S, Fujii T, Matsumoto K. [Effect of propionylmaridomycin in respiratory infections - a double blind study]. Kansenshogaku Zasshi. 1974 Sep;48(9):357-68. Japanese. PubMed PMID: 4218863.
5: Kunishige N, Kawamura K, Muroi M, Kishi T. Maridomycin, a new macrolide antibiotic. XII. A simple quantitative analysis of 9-propionylmaridomycin components. Chem Pharm Bull (Tokyo). 1975 Dec;23(12):3075-80. PubMed PMID: 1218448.
6: Muroi M, Izawa M, Kishi T. Maridomycin, a new macrolide antibiotic. 8. Isolation and structures of metabolites of 9-propionylmaridomycin. J Antibiot (Tokyo). 1974 Jun;27(6):449-59. PubMed PMID: 4853097.
7: Ono H, Harada S, Kishi T. Maridomycin, a new macrolide antibiotic. VII. Incorporation of labeled precursors into maridomycin and preparation of 14C-labeled 9-propionylmaridomycin. J Antibiot (Tokyo). 1974 Jun;27(6):442-8. PubMed PMID: 4853096.
8: Harada S, Muroi M, Kondo M, Tsuchiya K, Matsuzawa T. Chemical modification of maridomycin, a new macrolide antibiotic. Antimicrob Agents Chemother. 1973 Aug;4(2):140-8. PubMed PMID: 4790934; PubMed Central PMCID: PMC444519.
9: Kondo K. Analytical studies of maridomycin. II. Separation of 9-propionylmaridomycins by thin-layer chromatography. J Chromatogr. 1979 Feb 1;169:337-42. PubMed PMID: 536424.