Midecamycin acetate | CAS# 55881-07-7 | Antibiotic

MedKoo Cat#: 571498 | Name: Midecamycin acetate

Description:

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

Midecamycin acetate is a broad spectrum antibiotic active against Gram positive and some Gram negative strains. It can protect against effects of systemic and local infections.

Chemical Structure

Midecamycin acetate

CAS#55881-07-7 (acetate)

Theoretical Analysis

MedKoo Cat#: 571498

Name: Midecamycin acetate

CAS#: 55881-07-7 (acetate)

Chemical Formula: C45H71NO17

Exact Mass: 897.4722

Molecular Weight: 898.05

Elemental Analysis: C, 60.19; H, 7.97; N, 1.56; O, 30.29

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 #

55881-07-7 (acetate) 35457-80-8 (free base)

Synonym

Midecamycin acetate

IUPAC/Chemical Name

(2S,3S,4R,6S)-4-acetoxy-6-(((2R,3S,4R,5R,6S)-6-(((4R,5S,6S,7R,9R,10R,11E,13Z,16R)-10-acetoxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-(propionyloxy)oxacyclohexadeca-11,13-dien-6-yl)oxy)-4-(dimethylamino)-5-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2,4-dimethyltetrahydro-2H-pyran-3-yl propionate

InChi Key

GQNZGCARKRHPOH-YBODMYFASA-N

InChi Code

InChI=1S/C45H71NO17/c1-13-34(50)59-33-23-36(52)55-26(4)18-16-15-17-19-32(58-29(7)48)25(3)22-31(20-21-47)41(42(33)54-12)62-44-39(53)38(46(10)11)40(27(5)57-44)61-37-24-45(9,63-30(8)49)43(28(6)56-37)60-35(51)14-2/h15-17,19,21,25-28,31-33,37-44,53H,13-14,18,20,22-24H2,1-12H3/b16-15-,19-17+/t25-,26-,27-,28+,31+,32+,33-,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1

SMILES Code

O=CC[C@H]([C@@H]([C@@H](OC)[C@H](OC(CC)=O)C1)O[C@H]2[C@H](O)[C@@H](N(C)C)[C@@H]([C@@H](C)O2)O[C@H]3C[C@](OC(C)=O)(C)[C@H]([C@H](C)O3)OC(CC)=O)C[C@@H](C)[C@@H](OC(C)=O)/C=C/C=C\C[C@@H](C)OC1=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 898.05 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: Yoshida T, Watanabe T, Shomura T, Someya S, Okamoto R, Ishihara S, Miyauchi K, Kazuno Y. Bacteriological evaluation of midecamycin acetate and its metabolites. Jpn J Antibiot. 1982 Jun;35(6):1462-74. PubMed PMID: 6982352. 2: Sifrim D, Matsuo H, Janssens J, Vantrappen G. Comparison of the effects of midecamycin acetate and azithromycin on gastrointestinal motility in man. Drugs Exp Clin Res. 1994;20(3):121-6. PubMed PMID: 7956719. 3: Sifrim D, Janssens J, Vantrappen G. Effect of midecamycin acetate on gastrointestinal motility in humans. Int J Clin Pharmacol Res. 1992;12(2):71-9. PubMed PMID: 1428301. 4: Motohiro T, Tanaka K, Koga T, Shimada Y, Tomita N, Sakata Y, Fujimoto T, Nishiyama T, Nakajima T, Ishimoto K, Tominaga K, Yamashita F, Yukizane S, Suzuki K, Takajo N, Araki H, Kawano Y, Matsuura S, Imai S, Yuasa T, Tanaka Y, Tsugawa S, Nagayama K, Yamamoto M, Komatsu Y, Tanaka C, Matsuyama M, Koga T, Shiotsuki K, Kinoshita S, Haraguchi K, Matsuo H, Imuta F, Ohta M, Kubota K, Ichikawa K, Harada Y, Nakamura M. [Effect of midecamycin acetate on intestinal bacterial flora of children, and results of clinical study on midecamycin acetate in the treatment of mycoplasma pneumonia]. Jpn J Antibiot. 1982 Nov;35(11):2491-529. Japanese. PubMed PMID: 6763083. 5: Sifrim D, Janssens J, Vantrappen G. Comparison of the effects of midecamycin acetate and clarithromycin on gastrointestinal motility in man. Drugs Exp Clin Res. 1992;18(8):337-42. PubMed PMID: 1292916. 6: Morikawa K, Oseko F, Morikawa S, Iwamoto K. Immunomodulatory effects of three macrolides, midecamycin acetate, josamycin, and clarithromycin, on human T-lymphocyte function in vitro. Antimicrob Agents Chemother. 1994 Nov;38(11):2643-7. PubMed PMID: 7532933; PubMed Central PMCID: PMC188255. 7: Wan H, Zhao F, Zeng B. Direct electrochemistry and voltammetric determination of midecamycin at a multi-walled carbon nanotube coated gold electrode. Colloids Surf B Biointerfaces. 2011 Aug 1;86(1):247-50. doi: 10.1016/j.colsurfb.2011.03.037. Epub 2011 Apr 12. PubMed PMID: 21543194. 8: Mayama T, Maruyama K, Nakazawa T, Iida M. A survey of the side effects of midecamycin acetate (Miocamycin) dry syrup after marketing. Int J Clin Pharmacol Ther Toxicol. 1990 Jun;28(6):245-50. PubMed PMID: 2376425. 9: Motohiro T, Tanaka K, Koga T, Shimada Y, Tomita N, Sakata Y, Fujimoto T, Nishiyama T, Nakajima T, Ishimoto K, Tominaga K, Yamashita F, Watari H, Takajo N, Araki H, Kawano Y, Imai S, Yuasa T, Tanaka Y, Tsugawa S, Nagayama K, Yamamoto M, Komatsu R, Tanaka C, Yukizane S, Haraguchi K, Matsuo H, Ohta M, Kubota K, Shibuya Y, Oki S. [Clinical effect of midecamycin acetate on whooping cough]. Jpn J Antibiot. 1982 Aug;35(8):2022-33. Japanese. PubMed PMID: 6759695. 10: Soejima R, Niki Y, Hino J, Kishimoto T, Nakagawa Y, Sumi M, Saito A, Nakayama I, Tomizawa M, Hiraga Y, et al. [Double-blind comparative study of roxithromycin (RU 28965) and midecamycin acetate (MOM) in the treatment of pneumonia]. Kansenshogaku Zasshi. 1989 May;63(5):501-29. Japanese. PubMed PMID: 2506305. 11: Deguchi K, Yokota N, Koguchi M, Nakane Y, Fukushima Y, Fukayama S, Ishihara R, Oda S, Tanaka S, Sato K, et al. [Annual changes in susceptibility of clinical isolates to midecamycin acetate]. Jpn J Antibiot. 1990 Aug;43(8):1341-52. Japanese. PubMed PMID: 2283704. 12: Ma C, Wu L, Dai J, Zhou H, Li J, Sun X, Zhang K, Xia H, Wang Y. [Acylation specificity of midecamycin 3-O-acyltransferase within Streptomyces spiramyceticus F21]. Sheng Wu Gong Cheng Xue Bao. 2008 Dec;24(12):2086-92. Chinese. PubMed PMID: 19306580. 13: Deguchi K, Yokota N, Tanaka S, Fukayama S, Nishimura Y, Yoshihara H, Oda S, Matsumoto Y, Ikegami R, Sato K, et al. [Midecamycin acetate-susceptibility of clinical isolates from dental and oral surgical infections]. Jpn J Antibiot. 1986 Oct;39(10):2595-600. Japanese. PubMed PMID: 3643285. 14: Yokota M, Takeda U, Odaki M, Sasaki H, Niizato T, Kawaoto H, Watanabe H, Ishiwatari N, Koeda T. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miokamycin). Part II-1. Subacute toxicity in rats. Jpn J Antibiot. 1984 Jul;37(7):1321-32. PubMed PMID: 6333528. 15: Yokota M, Takeda U, Odaki M, Sasaki H, Kawaoto H, Itoh T, Koeda T. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miokamycin). Part I-1. Acute toxicity in mice. Jpn J Antibiot. 1984 Jul;37(7):1313-6. PubMed PMID: 6333526. 16: Yokota M, Takeda U, Odaki M, Sasaki H, Niizato T, Kawaoto H, Kumagai K, Suzuki H, Hayasaka H, Suzuki M, et al. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miokamycin). Part II-2. Subacute toxicity in rabbits. Jpn J Antibiot. 1984 Jul;37(7):1333-54. PubMed PMID: 6333529. 17: Yokota M, Takeda U, Odaki M, Sasaki H, Niizato T, Kawaoto H, Watanabe H, Itoh T, Ishiwatari N, Koeda T. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miokamycin). Part III-1. Chronic toxicity in rats. Jpn J Antibiot. 1984 Jul;37(7):1355-75. PubMed PMID: 6333530. 18: Yokota M, Takeda U, Odaki M, Sasaki H, Kawaoto H, Itoh T, Koeda T. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miocamycin). Part IV-4. Toxicity of metabolites of miocamycin: acute toxicity of Mb2 in mice. Jpn J Antibiot. 1984 Aug;37(8):1507-9. PubMed PMID: 6334174. 19: Yokota M, Takeda U, Odaki M, Sasaki H, Niizato T, Kawaoto H, Kumagai K, Suzuki H, Suzuki M, Sugiyama N, et al. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miokamycin). Part III-4. Chronic toxicity in beagle dogs: 26-week-treatment in male dogs. Jpn J Antibiot. 1984 Jul;37(7):1399-416. PubMed PMID: 6333533. 20: Yokota M, Takeda U, Odaki M, Sasaki H, Niizato T, Kawaoto H, Watanabe H, Ishiwatari N, Hayasaka H, Koeda T. Toxicological studies on a new macrolide antibiotic, midecamycin acetate (miocamycin). Part IV-12. Toxicity of metabolites of miocamycin: subacute toxicity of Mb12 in rats. Jpn J Antibiot. 1984 Aug;37(8):1552-64. PubMed PMID: 6334182.