Erythromycin propionate | CAS#134-36-1 | Macrolide antibiotic

MedKoo Cat#: 464339 | Name: Erythromycin propionate

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Description:

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

Erythromycin 2'-propionate is a macrolide antibiotic and an esterified form of erythromycin. It is active against S. aureus when used at a concentration of 1 µg/ml. Erythromycin 2'-propionate (1 mM) inhibits protein synthesis in a cell-free assay.

Chemical Structure

Erythromycin propionate

CAS#134-36-1 (propionate)

Theoretical Analysis

MedKoo Cat#: 464339

Name: Erythromycin propionate

CAS#: 134-36-1 (propionate)

Chemical Formula: C40H71NO14

Exact Mass: 789.4875

Molecular Weight: 790.00

Elemental Analysis: C, 60.82; H, 9.06; N, 1.77; O, 28.35

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	Back order
25mg	USD 750.00	Back order

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Related CAS #

7704-67-8 (thiocyanate) 114-07-8 (free base) 30010-41-4 (aspartate) 14271-02-4 (HCl) 16667-03-1 (glutamate) 3521-62-8 (estolate) 914076-30-5 (ethyl carbonate) 134-36-1 (propionate) 1264-62-6 (ethylsuccinate) 23067-13-2 (Gluceptate)

Synonym

Erythromycin 2'-Propionate; Erythromycin 2' Propionate; Erythromycin propionate; Propionylerythromycin; Erythromycin, 2'-propanoate;

IUPAC/Chemical Name

(2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl propionate

InChi Key

TYQXKHPOXXXCTP-CSLYCKPJSA-N

InChi Code

InChI=1S/C40H71NO14/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-29/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H3/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-/m1/s1

SMILES Code

CCC(O[C@@H]1[C@@H](N(C)C)C[C@@H](C)O[C@H]1O[C@@H]2[C@@H](C)[C@H](O[C@H]3C[C@]([C@@H](O)[C@H](C)O3)(OC)C)[C@@H](C)C(O[C@H](CC)[C@@]([C@H](O)[C@@H](C)C([C@H](C)C[C@@]2(C)O)=O)(C)O)=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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

An antibiotic.

In vitro activity:

The Th17 cells in the CSE-exposed DC/MLR group increased significantly compared with those in the control DC/MLR group (P < 0.05). Moreover, Th17 cells in the CD40-blocked CSE-exposed DC/MLR group and EM-treated CSE-exposed DC/MLR group were reduced compared with those in the CSE-exposed DC/MLR group (P < 0.05). Thus, these findings suggested that EM suppressed the CSE-exposed DC-mediated polarization of CD4+ T cells into Th17 cells and that this effect may be mediated through inhibition of the CD40/CD40L pathway. Reference: J Immunol Res. 2020; 2020: 1387952. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7201779/

In vivo activity:

Additionally, the ERM (erythromycin) treatment significantly reduced bone loss compared to the PC and JSM treatment groups (Figure 1b,c). Compared to the EtOH group, ERM, JSM, and PC treatment significantly decreased the gene expression of Nfatc1 and RANK, which are osteoclast differentiation-related factors in the gingiva (Figure 2a,b). Furthermore, ERM and JSM treatment significantly downregulated the expression of bone resorption activity-related factors (Acp5, Ctsk) (Figure 2c,d). Interestingly, ERM treatment significantly upregulated Del1 expression, compared to the EtOH group (Figure 2e). Reference: Antibiotics (Basel). 2021 Mar; 10(3): 312. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8002756/

Preparing Stock Solutions

The following data is based on the product molecular weight 790.00 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

Formulation protocol:

1. Liu J, Zhong X, He Z, Zhang J, Bai J, Liu G, Liang Y, Ya L, Qin X. Erythromycin Suppresses the Cigarette Smoke Extract-Exposed Dendritic Cell-Mediated Polarization of CD4+ T Cells into Th17 Cells. J Immunol Res. 2020 Jan 21;2020:1387952. doi: 10.1155/2020/1387952. PMID: 32411785; PMCID: PMC7201779. 2. Zhang H, Qiu SL, Tang QY, Zhou X, Zhang JQ, He ZY, Bai J, Li MH, Deng JM, Liang Y, Zhong XN. Erythromycin suppresses neutrophil extracellular traps in smoking-related chronic pulmonary inflammation. Cell Death Dis. 2019 Sep 12;10(9):678. doi: 10.1038/s41419-019-1909-2. PMID: 31515489; PMCID: PMC6742640. 3. Tamura H, Maekawa T, Domon H, Hiyoshi T, Hirayama S, Isono T, Sasagawa K, Yonezawa D, Takahashi N, Oda M, Maeda T, Tabeta K, Terao Y. Effects of Erythromycin on Osteoclasts and Bone Resorption via DEL-1 Induction in Mice. Antibiotics (Basel). 2021 Mar 17;10(3):312. doi: 10.3390/antibiotics10030312. PMID: 33803007; PMCID: PMC8002756. 4. Maekawa T, Tamura H, Domon H, Hiyoshi T, Isono T, Yonezawa D, Hayashi N, Takahashi N, Tabeta K, Maeda T, Oda M, Ziogas A, Alexaki VI, Chavakis T, Terao Y, Hajishengallis G. Erythromycin inhibits neutrophilic inflammation and mucosal disease by upregulating DEL-1. JCI Insight. 2020 Aug 6;5(15):e136706. doi: 10.1172/jci.insight.136706. PMID: 32603314; PMCID: PMC7455085.

In vitro protocol:

In vivo protocol:

1. Tamura H, Maekawa T, Domon H, Hiyoshi T, Hirayama S, Isono T, Sasagawa K, Yonezawa D, Takahashi N, Oda M, Maeda T, Tabeta K, Terao Y. Effects of Erythromycin on Osteoclasts and Bone Resorption via DEL-1 Induction in Mice. Antibiotics (Basel). 2021 Mar 17;10(3):312. doi: 10.3390/antibiotics10030312. PMID: 33803007; PMCID: PMC8002756. 2. Maekawa T, Tamura H, Domon H, Hiyoshi T, Isono T, Yonezawa D, Hayashi N, Takahashi N, Tabeta K, Maeda T, Oda M, Ziogas A, Alexaki VI, Chavakis T, Terao Y, Hajishengallis G. Erythromycin inhibits neutrophilic inflammation and mucosal disease by upregulating DEL-1. JCI Insight. 2020 Aug 6;5(15):e136706. doi: 10.1172/jci.insight.136706. PMID: 32603314; PMCID: PMC7455085.

1: Wiegand RG, Chun AH. Serum protein binding of erythromycin and erythromycin 2'-propionate ester. J Pharm Sci. 1972 Mar;61(3):425-8. doi: 10.1002/jps.2600610322. PMID: 5062519.