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MedKoo Cat#: 317605 | Name: Dicloxacillin

Description:

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

Dicloxacillin (INN) is a narrow-spectrum β-Lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin binds to penicillin binding proteins (PBP) located on the inner membrane of the bacterial cell wall. It also inhibits the cross-linkage of peptidoglycan, a critical component of bacterial cell walls. This leads to the inhibition of bacterial cell wall synthesis and eventually causes cell lysis. Dicloxacillin is available under a variety of trade names including Diclocil (BMS). (Source: https://en.wikipedia.org/wiki/Dicloxacillin).

Chemical Structure

Dicloxacillin
CAS#3116-76-5 (free acid)

Theoretical Analysis

MedKoo Cat#: 317605

Name: Dicloxacillin

CAS#: 3116-76-5 (free acid)

Chemical Formula: C19H17Cl2N3O5S

Exact Mass: 469.0266

Molecular Weight: 470.33

Elemental Analysis: C, 48.52; H, 3.64; Cl, 15.08; N, 8.93; O, 17.01; S, 6.82

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 #
3116-76-5 (free acid) 13412-64-1 (sodium hydrate)
Synonym
Dicloxacillin; Dicloxacilina; Dicloxacilline; Dicloxacillinum; Dicloxacycline; Dynapen; Diclocil;
IUPAC/Chemical Name
(2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChi Key
YFAGHNZHGGCZAX-JKIFEVAISA-N
InChi Code
InChI=1S/C19H17Cl2N3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
SMILES Code
CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=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
Soluble in DMSO, not in water
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 470.33 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: Wu G, Zheng Y, Zhou H, Hu X, Liu J, Zhai Y, Zhu M, Wu L, Shentu J. Safety and pharmacokinetics of dicloxacillin in healthy Chinese volunteers following single and multiple oral doses. Drug Des Devel Ther. 2015 Oct 16;9:5687-95. doi: 10.2147/DDDT.S92117. eCollection 2015. PubMed PMID: 26527863; PubMed Central PMCID: PMC4621192. 2: Stenger M, Hendel K, Bollen P, Licht PB, Kolmos HJ, Klitgaard JK. Assessments of Thioridazine as a Helper Compound to Dicloxacillin against Methicillin-Resistant Staphylococcus aureus: In Vivo Trials in a Mouse Peritonitis Model. PLoS One. 2015 Aug 12;10(8):e0135571. doi: 10.1371/journal.pone.0135571. eCollection 2015. PubMed PMID: 26267376; PubMed Central PMCID: PMC4534400. 3: Pottegård A, Henriksen DP, Madsen KG, Hellfritzsch M, Damkier P, Stage TB. Change in International Normalized Ratio Among Patients Treated With Dicloxacillin and Vitamin K Antagonists. JAMA. 2015 Jul 21;314(3):296-7. doi: 10.1001/jama.2015.6669. PubMed PMID: 26197191. 4: Villegas-Guzman P, Silva-Agredo J, González-Gómez D, Giraldo-Aguirre AL, Flórez-Acosta O, Torres-Palma RA. Evaluation of water matrix effects, experimental parameters, and the degradation pathway during the TiO2 photocatalytical treatment of the antibiotic dicloxacillin. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2015;50(1):40-8. doi: 10.1080/10934529.2015.964606. PubMed PMID: 25438130. 5: Bhinge SD, Malipatil SM, Sonawane LV. Bioanalytical method development and validation for simultaneous estimation of cefixime and dicloxacillin by RP-HPLC in human plasma. Acta Chim Slov. 2014;61(3):580-6. PubMed PMID: 25286213. 6: Villegas-Guzman P, Silva-Agredo J, Giraldo-Aguirre AL, Flórez-Acosta O, Petrier C, Torres-Palma RA. Enhancement and inhibition effects of water matrices during the sonochemical degradation of the antibiotic dicloxacillin. Ultrason Sonochem. 2015 Jan;22:211-9. doi: 10.1016/j.ultsonch.2014.07.006. Epub 2014 Jul 14. PubMed PMID: 25069890. 7: Poulsen MØ, Schøler L, Nielsen A, Skov MN, Kolmos HJ, Kallipolitis BH, Olsen A, Klitgaard JK. Combination therapy with thioridazine and dicloxacillin combats meticillin-resistant Staphylococcus aureus infection in Caenorhabditis elegans. J Med Microbiol. 2014 Sep;63(Pt 9):1174-80. doi: 10.1099/jmm.0.071837-0. Epub 2014 Jun 9. PubMed PMID: 24913562. 8: Rasmussen JB, Knudsen JD, Arpi M, Schønheyder HC, Benfield T, Ostergaard C. Relative efficacy of cefuroxime versus dicloxacillin as definitive antimicrobial therapy in methicillin-susceptible Staphylococcus aureus bacteraemia: a propensity-score adjusted retrospective cohort study. J Antimicrob Chemother. 2014 Feb;69(2):506-14. doi: 10.1093/jac/dkt375. Epub 2013 Sep 26. PubMed PMID: 24078468. 9: Acharya DR, Patel DB. Development and Validation of RP-HPLC Method for Simultaneous Estimation of Cefpodoxime Proxetil and Dicloxacillin Sodium in Tablets. Indian J Pharm Sci. 2013 Jan;75(1):31-5. doi: 10.4103/0250-474X.113538. PubMed PMID: 23901158; PubMed Central PMCID: PMC3719147. 10: Nissen JL, Skov R, Knudsen JD, Ostergaard C, Schønheyder HC, Frimodt-Møller N, Benfield T. Effectiveness of penicillin, dicloxacillin and cefuroxime for penicillin-susceptible Staphylococcus aureus bacteraemia: a retrospective, propensity-score-adjusted case-control and cohort analysis. J Antimicrob Chemother. 2013 Aug;68(8):1894-900. doi: 10.1093/jac/dkt108. Epub 2013 Apr 18. PubMed PMID: 23599360.

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