Rosaramicin stearate | CAS# 51547-64-9 (stearate) | macrolide antibiotic

MedKoo Cat#: 412948 | Name: Rosaramicin stearate

Description:

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

Rosaramicin stearate is a macrolide antibiotic similar to erythromycin. This compound is more effective against Gram-negative bacteria than erythromycin, especially in the prostate where rosamaricin was shown to be more concentrated than erythromycin in dogs. Rosamaricin has antibiotic activity against Neisseria gonorrhoeae, Chlamydia trachomatis, Ureaplasma urealyticum and Mycoplasma hominis. When the drug was compared with penicillin G in the treatment of pneumococcal meningitis in rabbits it was found to be less effective than penicillin G, as measured by bacterial clearance from cerebrospinal fluid and by treatment outcome. No information on the current use of this compound is available.

Chemical Structure

Rosaramicin stearate

CAS#51547-64-9 (stearate)

Theoretical Analysis

MedKoo Cat#: 412948

Name: Rosaramicin stearate

CAS#: 51547-64-9 (stearate)

Chemical Formula: C49H87NO11

Exact Mass: 865.6279

Molecular Weight: 866.23

Elemental Analysis: C, 67.94; H, 10.12; N, 1.62; O, 20.32

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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Related CAS #

60802-40-6 (Na+ Phosphate) 55103-30-5 (butyrate) 35834-26-5 (free base) 51481-64-2 (propionate) 51547-64-9 (stearate)

Synonym

Rosaramicin stearate; Sch14947 Stearate; Sch-14947 Stearate; Sch14947 Stearate

IUPAC/Chemical Name

2-((1S,2R,3R,7R,8S,9S,10R,12R,16S,E)-9-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl)acetaldehyde stearate

InChi Key

NTRKBPHPPMYMKJ-VHXUMFCXSA-N

InChi Code

InChI=1S/C31H51NO9.C18H36O2/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30;1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3;2-17H2,1H3,(H,19,20)/b12-10+;/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+;/m1./s1

SMILES Code

CCCCCCCCCCCCCCCCCC(O)=O.CC[C@H]1OC(C[C@H]([C@@H]([C@H]([C@H](C[C@H](C(/C=C/[C@@]2(O[C@H]2[C@@H]1C)C)=O)C)CC=O)O[C@@H]3O[C@@H](C[C@H](N(C)C)[C@H]3O)C)C)O)=O

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

Soluble in DMSO

Shelf Life

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 866.23 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: Massa T, Davis GJ, Schiavo D, Sinha DP, Szot RJ, Black HE, Schwartz E. Tapetal changes in beagle dogs. II. Ocular changes after intravenous administration of a macrolide antibiotic--rosaramicin. Toxicol Appl Pharmacol. 1984 Feb;72(2):195-200. PubMed PMID: 6695372. 2: Funaishi K, Kawamura K, Satoh F, Hiramatsu M, Hagiwara M, Okanish M. New analogues of rosaramicin isolated from a Micromonospora strain. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties. J Antibiot (Tokyo). 1990 Aug;43(8):938-47. PubMed PMID: 2088343. 3: Baughn RE, Musher DM, Adams CB, Knox JM. Evaluation of rosaramicin phosphate in treatment of experimental syphilis in rabbits. Antimicrob Agents Chemother. 1981 Jan;19(1):117-21. PubMed PMID: 7018381; PubMed Central PMCID: PMC181368. 4: Robson HG, Shah PP, Lalonde RG, Hayes L, Senikas VM. Comparison of rosaramicin and erythromycin stearate for treatment of cervical infection with Chlamydia trachomatis. Sex Transm Dis. 1983 Jul-Sep;10(3):130-4. PubMed PMID: 6648747. 5: Darne JF, Ridgway GL, Oriel JD. Rosaramicin and tetracycline in the treatment of non-gonococcal urethritis. A comparison of clinical and microbiological results. Br J Vener Dis. 1982 Apr;58(2):117-20. PubMed PMID: 7039760; PubMed Central PMCID: PMC1046020. 6: Lin CC, Kim HK, Marco A, Radwanski E, Symchowicz S. Pharmacokinetics and metabolism of [14C]rosaramicin in dogs. Antimicrob Agents Chemother. 1986 May;29(5):753-6. PubMed PMID: 3729339; PubMed Central PMCID: PMC284148. 7: Lin CC, Chung M, Gural R, Schuessler D, Kim HK, Radwanski E, Marco A, DiGiore C, Symchowicz S. Pharmacokinetics and metabolism of rosaramicin in humans. Antimicrob Agents Chemother. 1984 Oct;26(4):522-6. PubMed PMID: 6517543; PubMed Central PMCID: PMC179957. 8: Nolan CM, Monson TP, Ulmer WC Jr. Rosaramicin versus penicillin G in experimental Pneumococcal meningitis. Antimicrob Agents Chemother. 1979 Dec;16(6):776-80. PubMed PMID: 43705; PubMed Central PMCID: PMC352952. 9: Lin C, Kim H, Schuessler D, Oden E, Symchowicz S. High-pressure liquid chromatographic method for determination of rosaramicin in humans. Antimicrob Agents Chemother. 1980 Nov;18(5):780-3. PubMed PMID: 7447432; PubMed Central PMCID: PMC284091. 10: Smith JA, Isaac-Renton JL, Jellett JF, Chow AW, Ngui-Yen J. Inhibitory and lethal activities of rosaramicin, erythromycin, and clindamycin against Campylobacter fetus subsp jejuni and intestinalis. Am J Vet Res. 1983 Aug;44(8):1605-6. PubMed PMID: 6625312. 11: Batteiger BE, Zwickl BE, French ML, Jones RB. Women at risk for gonorrhea: comparison of rosaramicin and ampicillin plus probenecid in the eradication of Neisseria gonorrhoeae, Chlamydia trachomatis and genital mycoplasmas. Sex Transm Dis. 1985 Jan-Mar;12(1):1-4. PubMed PMID: 3890223. 12: Nakajima S, Kojiri K, Morishima H, Okanishi M. New analogs of rosaramicin isolated from a Micromonospora strain. II. Structure determination. J Antibiot (Tokyo). 1990 Aug;43(8):1006-9. PubMed PMID: 2211347. 13: Puar MS, Schumacher D, Mollitor T, Rosenkrantz B, Jaret RS, McPhail AT. Solid state thermal degradation products of rosaramicin. J Antibiot (Tokyo). 1992 Sep;45(9):1540-3. PubMed PMID: 1429241. 14: Lin C, Puar MS, Schuessler D, Prananik BN, Symchowicz S. Isolation and identification of a metabolite of rosaramicin in human urine. Drug Metab Dispos. 1984 Jan-Feb;12(1):51-6. PubMed PMID: 6141912. 15: Smith TF. In vitro susceptibility of Ureaplasma urealyticum to rosaramicin. Antimicrob Agents Chemother. 1979 Jul;16(1):106-8. PubMed PMID: 475368; PubMed Central PMCID: PMC352799. 16: Juvakoski T, Allgulander C, Lassus A. Rosaramicin and tetracycline treatment in Chlamydia trachomatis-positive and -negative nongonococcal urethritis. Sex Transm Dis. 1981 Jan-Mar;8(1):12-5. PubMed PMID: 7221804. 17: Stoehr GP, Juhl RP, Veals J, Symchowicz S, Gural R, Lin C, McDonald RH. The excretion of rosaramicin in breast milk. J Clin Pharmacol. 1985 Mar;25(2):89-94. PubMed PMID: 3988965. 18: Landesman SH, Cummings M, Gruarin A, Bernheimer H. Susceptibility of multiply antibiotic-resistant pneumococci to the new beta-lactam drugs and rosaramicin. Antimicrob Agents Chemother. 1981 Apr;19(4):675-7. PubMed PMID: 7247389; PubMed Central PMCID: PMC181500. 19: Bowie WR. In vitro activity of rosaramicin against Chlamydia trachomatis. Antimicrob Agents Chemother. 1980 Dec;18(6):978-9. PubMed PMID: 7235684; PubMed Central PMCID: PMC353001. 20: Ahonkhai VI, Cherubin CE, Sierra MF, Bokkenheuser VD, Shulman MA, Mosenthal AC. In vitro susceptibility of Campylobacter fetus subsp. jejuni to N-formimidoyl thienamycin, rosaramicin, cefoperazone, and other antimicrobial agents. Antimicrob Agents Chemother. 1981 Dec;20(6):850-1. PubMed PMID: 6459767; PubMed Central PMCID: PMC181813.