Rosaramicin (free base)

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MedKoo CAT#: 461415

CAS#: 35834-26-5 (free base)

Description: Rosaramicin (free base) is an antibacterial substance that is chemically a lipid-soluble basic macrolide similar to erythromycin but with a better activity against Gram-negative bacteria.

Chemical Structure

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Rosaramicin (free base)
CAS# 35834-26-5 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 461415
Name: Rosaramicin (free base)
CAS#: 35834-26-5 (free base)
Chemical Formula: C31H51NO9
Exact Mass: 581.36
Molecular Weight: 581.740
Elemental Analysis: C, 64.00; H, 8.84; N, 2.41; O, 24.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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; M 4365A2; M-4365A2 M4365A2;

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

InChi Key: IUPCWCLVECYZRV-JZMZINANSA-N

InChi Code: InChI=1S/C31H51NO9/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/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1

SMILES Code: CC[C@@H]1[C@@H](C)[C@H]2[C@@](/C=C/C([C@H](C)C[C@H](CC=O)[C@H](O[C@H]3[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3)[C@@H](C)[C@H](O)CC(O1)=O)=O)(C)O2

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: >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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 581.74 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.