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MedKoo Cat#: 573825 | Name: Amoxicillin open ring dimer

Description:

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

Amoxicillin open ring dimer is an impurity of Amoxicillin --- a β-lactam family antibiotic that is commonly used in conjunction with clavulanic acid to the treat bacterial infections.

Chemical Structure

Amoxicillin open ring dimer
Amoxicillin open ring dimer
CAS#73590-06-4 (dimer)

Theoretical Analysis

MedKoo Cat#: 573825

Name: Amoxicillin open ring dimer

CAS#: 73590-06-4 (dimer)

Chemical Formula: C32H36N6Na2O10S2

Exact Mass: 774.1730

Molecular Weight: 774.77

Elemental Analysis: C, 49.61; H, 4.68; N, 10.85; Na, 5.93; O, 20.65; S, 8.28

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Related CAS #
26787-78-0 (anhydrous) 34642-77-8 (sodium) 61336-70-7 (hydrate) 119229-00-4 (embonate) 73590-06-4 (dimer) 26889-93-0 (L-Amoxicillin)
Synonym
Amoxicillin dimer; Amoxicillin open ring dimer; Amoxicillin related compound J
IUPAC/Chemical Name
(2S,5R,6R)-6-((R)-2-((R)-2-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-2-((2R,4S)-4-carboxy-5,5-dimethylthiazolidin-2-yl)acetamido)-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChi Key
GERXQFMVSQUXHT-BOUYBQKTSA-N
InChi Code
InChI=1S/C32H38N6O10S2/c1-31(2)21(29(45)46)37-26(49-31)19(35-23(41)17(33)13-5-9-15(39)10-6-13)25(43)34-18(14-7-11-16(40)12-8-14)24(42)36-20-27(44)38-22(30(47)48)32(3,4)50-28(20)38/h5-12,17-22,26,28,37,39-40H,33H2,1-4H3,(H,34,43)(H,35,41)(H,36,42)(H,45,46)(H,47,48)/t17-,18-,19-,20-,21+,22+,26-,28-/m1/s1
SMILES Code
O=C(O)[C@H](N1C2=O)C(C)(S[C@@]1([C@@H]2NC([C@@H](C3=CC=C(C=C3)O)NC([C@H]([C@H]4SC(C)([C@@H](N4)C(O)=O)C)NC([C@@H](C5=CC=C(C=C5)O)N)=O)=O)=O)[H])C
Appearance
White to Light Yellow Solid
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 774.77 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: Lu CY, Feng CH. Identification of dimer impurities in ampicillin and amoxicillin by capillary LC and tandem mass spectrometry. J Sep Sci. 2007 Feb;30(3):329-32. doi: 10.1002/jssc.200600362. PMID: 17396590. 2: Chong XM, Zou WB, Yao SC, Hu CQ. Rapid Analysis of the Quality of Amoxicillin and Clavulanate Potassium Tablets Using Diffuse Reflectance Near-Infrared Spectroscopy. AAPS PharmSciTech. 2017 May;18(4):1311-1317. doi: 10.1208/s12249-016-0602-3. Epub 2016 Aug 5. PMID: 27495163. 3: Chong XM, Li J, Wang Y, Wang C, Wang LX, Yao SC, Hu CQ. [The control of the critical quality attributes of amoxicillin and clavulanate potassium tablet]. Yao Xue Xue Bao. 2016 Jul;51(7):1121-4. Chinese. PMID: 29897214. 4: Arabski M, Kazmierczak P, Wisniewska-Jarosinska M, Poplawski T, Klupinska G, Chojnacki J, Drzewoski J, Blasiak J. Interaction of amoxicillin with DNA in human lymphocytes and H. pylori-infected and non-infected gastric mucosa cells. Chem Biol Interact. 2005 Feb 28;152(1):13-24. doi: 10.1016/j.cbi.2005.01.004. PMID: 15766919. 5: Grujic S, Vasiljevic T, Lausevic M, Ast T. Study on the formation of an amoxicillin adduct with methanol using electrospray ion trap tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008;22(1):67-74. doi: 10.1002/rcm.3333. PMID: 18050261. 6: Shmakov RG, Prikhodko A, Polushkina E, Shmakova E, Pyregov A, Bychenko V, Priputnevich TV, Dolgushin GO, Yarotskaya E, Pekarev O, Bolibok N, Degtyarev D, Sukhikh GT. Clinical course of novel COVID-19 infection in pregnant women. J Matern Fetal Neonatal Med. 2022 Dec;35(23):4431-4437. doi: 10.1080/14767058.2020.1850683. Epub 2020 Nov 29. PMID: 33249969; PMCID: PMC7711745. 7: De Pourcq P, Hoebus J, Roets E, Hoogmartens J, Vanderhaeghe H. Quantitative determination of amoxicillin and its decomposition products by high-performance liquid chromatography. J Chromatogr. 1985 Mar 15;321(2):441-9. doi: 10.1016/s0021-9673(01)90462-5. PMID: 3988846. 8: Weisnicht AM, Byrne R, Henkel EB, Harding SA, Kostelyna SP, Schady D, Lai J, Stubbs LA. Recurrent Rash in an 11-Year-Old Boy With Pericardial and Pleural Effusions. Pediatrics. 2022 Nov 1;150(5):e2021055524. doi: 10.1542/peds.2021-055524. PMID: 36305212. 9: Szabó L, Tóth T, Rácz G, Takács E, Wojnárovits L. Drugs with susceptible sites for free radical induced oxidative transformations: the case of a penicillin. Free Radic Res. 2016;50(1):26-38. doi: 10.3109/10715762.2015.1100729. Epub 2015 Nov 11. PMID: 26431250. 10: Nandy P, Santra RC, Lahiri D, Nag M, Das S. In Situ Reactivity of Electrochemically Generated Nitro Radical Anion on Tinidazole and Its Monomeric and Dimeric CuII Complexes on Model Biological Targets with Relative Manifestation of Preventing Bacterial Biofilm Formation. ACS Omega. 2022 Mar 1;7(10):8268-8280. doi: 10.1021/acsomega.1c04822. PMID: 35309450; PMCID: PMC8928527. 11: Chaput C, Ecobichon C, Pouradier N, Rousselle JC, Namane A, Boneca IG. Role of the N-Acetylmuramoyl-l-Alanyl Amidase, AmiA, of Helicobacter pylori in Peptidoglycan Metabolism, Daughter Cell Separation, and Virulence. Microb Drug Resist. 2016 Sep;22(6):477-86. doi: 10.1089/mdr.2016.0070. Epub 2016 Jul 22. PMID: 27447281; PMCID: PMC5036311. 12: Di Rocco M, Moloney M, O'Beirne T, Earley S, Berendsen B, Furey A, Danaher M. Development and validation of a quantitative confirmatory method for 30 β-lactam antibiotics in bovine muscle using liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A. 2017 Jun 2;1500:121-135. doi: 10.1016/j.chroma.2017.04.022. Epub 2017 Apr 12. PMID: 28449875. 13: Meziane-Cherif D, Lambert T, Dupêchez M, Courvalin P, Galimand M. Genetic and biochemical characterization of OXA-63, a new class D beta-lactamase from Brachyspira pilosicoli BM4442. Antimicrob Agents Chemother. 2008 Apr;52(4):1264-8. doi: 10.1128/AAC.00684-07. Epub 2008 Jan 22. PMID: 18212108; PMCID: PMC2292554. 14: Lu YH, Yen HW, Lin TH, Huang CH, Lee KT, Wang WM, Wu DC, Voon WC, Lai WT, Sheu SH. Changes of coronary risk factors after eradication of Helicobacter pylori infection. Kaohsiung J Med Sci. 2002 Jun;18(6):266-72. PMID: 12355926. 15: Bundgaard H. Polymerization of penicillins. II. Kinetics and mechanism of dimerization and self-catalyzed hydrolysis of amoxycillin in aqueous solution. Acta Pharm Suec. 1977;14(1):47-66. PMID: 16434. 16: Connor SC, Everett JR, Jennings KR, Nicholson JK, Woodnutt G. High resolution 1H NMR spectroscopic studies of the metabolism and excretion of ampicillin in rats and amoxycillin in rats and man. J Pharm Pharmacol. 1994 Feb;46(2):128-34. doi: 10.1111/j.2042-7158.1994.tb03755.x. PMID: 8021801. 17: Markiewicz H, Krumrych W, Gehrke M. The effect of supportive E. coli mastitis treatment on PMN chemiluminescence and subpopulations of T lymphocytes. Pol J Vet Sci. 2013;16(4):671-7. doi: 10.2478/pjvs-2013-0095. PMID: 24597301. 18: Rodriguez WJ, Khan WH, Sait T, Chhabra OP, Guarinello A, Smith AW, Ahmad S. Sultamicillin (sulbactam/ampicillin) versus amoxycillin in the treatment of acute otitis media in children. J Int Med Res. 1990;18 Suppl 4:78D-84D. PMID: 2282972. 19: Bundgaard H. Polymerization of penicillins. III. Structural effects influencing rate of dimerization of amino-penicillins in aqueous solution. Acta Pharm Suec. 1977;14(1):67-80. PMID: 16435.