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MedKoo Cat#: 328101 | Name: Cethromycin

Description:

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

Cethromycin, also known as ABT-773 and A-195773, has a similar mechanism of action to telithromycin with an apparently better safety profile. Cethromycin displays in vitro activity against selected gram-positive, gram-negative, and atypical bacteria. The proposed indication of cethromycin is treatment of mild to moderate community-acquired bacterial pneumonia in patients. Cethromycin has an orphan drug designation for tularemia, plague, and anthrax prophylaxis. Preliminary data on adverse effects suggest that cethromycin is safe and gastrointestinal adverse effects appear to be dose-related.

Chemical Structure

Cethromycin
CAS#205110-48-1

Theoretical Analysis

MedKoo Cat#: 328101

Name: Cethromycin

CAS#: 205110-48-1

Chemical Formula: C42H59N3O10

Exact Mass: 765.4200

Molecular Weight: 765.95

Elemental Analysis: C, 65.86; H, 7.76; N, 5.49; O, 20.89

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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Synonym
Cethromycin; ABT-773; ABT 773; ABT773; A-195773; A 195773; A195773
IUPAC/Chemical Name
(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(((E)-3-(quinolin-3-yl)allyl)oxy)octahydro-2H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetraone
InChi Key
PENDGIOBPJLVBT-ONLVEXIXSA-N
InChi Code
InChI=1S/C42H59N3O10/c1-11-32-42(8)36(44-40(50)55-42)25(4)33(46)23(2)21-41(7,51-18-14-15-28-20-29-16-12-13-17-30(29)43-22-28)37(26(5)34(47)27(6)38(49)53-32)54-39-35(48)31(45(9)10)19-24(3)52-39/h12-17,20,22-27,31-32,35-37,39,48H,11,18-19,21H2,1-10H3,(H,44,50)/b15-14+/t23-,24-,25+,26+,27-,31+,32-,35-,36-,37-,39+,41-,42-/m1/s1
SMILES Code
CC[C@H]1OC([C@@H](C([C@@H]([C@H]([C@@](C[C@H](C([C@@H]([C@H]2NC(O[C@]12C)=O)C)=O)C)(OC/C=C/C3=CN=C(C=CC=C4)C4=C3)C)O[C@@H]5O[C@@H](C[C@H](N(C)C)[C@H]5O)C)C)=O)C)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 765.95 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
1: Liang JH. Introduction of a nitrogen-containing side chain appended on C-10 of cethromycin leads to reduced CYP3A4 inhibition (WO2014049356A1). Expert Opin Ther Pat. 2015 Jan;25(1):119-23. doi: 10.1517/13543776.2014.971754. Epub 2014 Oct 18. Review. PubMed PMID: 25327846. 2: Mansour H, Chahine EB, Karaoui LR, El-Lababidi RM. Cethromycin: a new ketolide antibiotic. Ann Pharmacother. 2013 Mar;47(3):368-79. doi: 10.1345/aph.1R435. Epub 2013 Mar 5. Review. PubMed PMID: 23463743. 3: Park B, Min YH. Inducible expression of erm(B) by the ketolides telithromycin and cethromycin. Int J Antimicrob Agents. 2015 Aug;46(2):226-7. doi: 10.1016/j.ijantimicag.2015.05.001. Epub 2015 Jun 3. PubMed PMID: 26088553. 4: English ML, Fredericks CE, Milanesio NA, Rohowsky N, Xu ZQ, Jenta TR, Flavin MT, Eiznhamer DA. Cethromycin versus clarithromycin for community-acquired pneumonia: comparative efficacy and safety outcomes from two double-blinded, randomized, parallel-group, multicenter, multinational noninferiority studies. Antimicrob Agents Chemother. 2012 Apr;56(4):2037-47. doi: 10.1128/AAC.05596-11. Epub 2012 Jan 30. PubMed PMID: 22290969; PubMed Central PMCID: PMC3318370. 5: Wagh B, Paul T, Debrosse C, Klepacki D, Small MC, Mackerell AD Jr, Andrade RB. Desmethyl Macrolides: Synthesis and Evaluation of 4,8,10-Tridesmethyl Cethromycin. ACS Med Chem Lett. 2013 Nov 14;4(11):1114-1118. PubMed PMID: 24470840; PubMed Central PMCID: PMC3901159. 6: Rosenzweig JA, Brackman SM, Kirtley ML, Sha J, Erova TE, Yeager LA, Peterson JW, Xu ZQ, Chopra AK. Cethromycin-mediated protection against the plague pathogen Yersinia pestis in a rat model of infection and comparison with levofloxacin. Antimicrob Agents Chemother. 2011 Nov;55(11):5034-42. doi: 10.1128/AAC.00632-11. Epub 2011 Aug 22. PubMed PMID: 21859946; PubMed Central PMCID: PMC3195012. 7: Sullivan DJ, Liu Y, Mott BT, Kaludov N, Martinov MN. Discovery of Novel Liver-Stage Antimalarials through Quantum Similarity. PLoS One. 2015 May 7;10(5):e0125593. doi: 10.1371/journal.pone.0125593. eCollection 2015. PubMed PMID: 25951139; PubMed Central PMCID: PMC4423929. 8: Liapikou A, Cilloniz C, Mensa J, Torres A. New antimicrobial approaches to gram positive respiratory infections. Pulm Pharmacol Ther. 2015 Jun;32:137-43. doi: 10.1016/j.pupt.2014.05.003. Epub 2014 May 27. Review. PubMed PMID: 24878422. 9: Krokidis MG, Márquez V, Wilson DN, Kalpaxis DL, Dinos GP. Insights into the mode of action of novel fluoroketolides, potent inhibitors of bacterial protein synthesis. Antimicrob Agents Chemother. 2014;58(1):472-80. doi: 10.1128/AAC.01994-13. Epub 2013 Nov 4. PubMed PMID: 24189263; PubMed Central PMCID: PMC3910732. 10: Georgopapadakou NH. The wobbly status of ketolides: where do we stand? Expert Opin Investig Drugs. 2014 Oct;23(10):1313-9. doi: 10.1517/13543784.2014.954036. Epub 2014 Aug 25. PubMed PMID: 25154307.