Cephalexin | CAS#15686-71-2 | Antibiotic

MedKoo Cat#: 317456 | Name: Cephalexin

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Description:

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

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic of the cephalosporin family. It is bactericidal and acts by inhibiting synthesis of the peptidoglycan layer of the bacterial cell wall. As cefalexin closely resembles d-alanyl-d-alanine, an amino acid ending on the peptidoglycan layer of the cell wall, it is able to irreversibly bind to the active site of PBP, which is essential for the synthesis of the cell wall. It is most active against gram-positive cocci, and has moderate activity against some gram-negative bacilli.

Chemical Structure

Cephalexin

CAS#15686-71-2 (free)

Theoretical Analysis

MedKoo Cat#: 317456

Name: Cephalexin

CAS#: 15686-71-2 (free)

Chemical Formula: C16H17N3O4S

Exact Mass: 0.0000

Molecular Weight: 347.89

Elemental Analysis: C, 55.32; H, 4.93; N, 12.10; O, 18.42; S, 9.23

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 650.00	2 Weeks

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Related CAS #

15686-71-2 (free) 23325-78-2 (hydrate) 38932-40-0 (soidum) 105879-42-3 (HCl) 53950-14-4 (lysine)

Synonym

Cefalexin; Cephalexin

IUPAC/Chemical Name

(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key

ZAIPMKNFIOOWCQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)

SMILES Code

CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O

Appearance

Solid powder

Purity

>95% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Cephalexin (Cefalexin) is an antibiotic that can treat a number of bacterial infections.

In vitro activity:

By assessing the bactericidal effects on four bacterial inoculum sizes, it was shown that macrophages can cooperate with cephalexin on inoculum sizes lower than 106 CFU/mL and conversely, protect S. aureus from cephalexin killing activity at the highest inoculum size. Cell analysis by flow cytometry revealed that macrophages were rapidly overwhelmed when exposed to large inoculums. Increasing the initial inoculum size from 105 to 107 CFU/mL increased macrophage death and decreased their ability to kill bacteria from six hours after exposure to bacteria. The addition of cephalexin at 16-fold MIC to 105 and 106 CFU/mL inoculums allowed the macrophages to survive and to maintain their bactericidal activity as if they were exposed to a small bacterial inoculum. However, with the highest inoculum size of 107 CFU/mL, the final bacterial counts in the supernatant were higher with macrophages plus cephalexin than with cephalexin alone. Reference: BMC Vet Res. 2021 Jan 7;17(1):23. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/33413376/

In vivo activity:

The objective of this study was to evaluate the in vivo effects of cephalexin on selection of Escherichia coli resistant to extended-spectrum cephalosporins. A cohort study was conducted on 13 dogs presenting clinical signs of pyoderma and treated with cephalexin and 22 healthy dogs that had not been treated with antibiotics during the previous six months. Selective plating of faeces on MacConkey agar plates containing cefotaxime (CTX) yielded growth of CTX-resistant E. coli for eight of the 13 treated dogs (62%), whereas no growth was observed for any of the control dogs (Fisher exact test, P<0.001). PCR and sequence analysis identified bla(CMY-2) in all eight dogs. PCR-based replicon typing and restriction fragment length polymorphism (RFLP) of E. coli transformants revealed location of bla(CMY-2) on indistinguishable IncI1 plasmids in five of the eight dogs. One representative of these five epidemiologically related IncI1 plasmids was further characterized as sequence type (ST2) by plasmid multilocus sequence typing (pMLST). E. coli from the remaining three dogs harboured bla(CMY-2) on distinct plasmids with non-typeable replicons. A single isolate was classified as an extraintestinal pathogenic E. coli (ExPEC) due to the presence of iutA, papC and sfa/foc. The results provide a strong indication that cephalexin selects for E. coli producing plasmid-borne CMY-2 β-lactamase. The isolation of a specific IncI1 plasmid carrying bla(CMY-2) from five epidemiologically unrelated dogs suggests that cephalexin use may contribute to the spread of this plasmid lineage among Danish dogs. Reference: Vet Microbiol. 2011 Aug 5;151(3-4):404-8. https://linkinghub.elsevier.com/retrieve/pii/S0378-1135(11)00153-2

	Solvent	mg/mL	mM	comments
Solubility
	Water	10.0	28.79

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 347.89 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:

In vitro protocol:

1. Lallemand EA, Zemirline C, Toutain PL, Bousquet-Melou A, Ferran AA, Boullier S. Dynamic interactions between cephalexin and macrophages on different Staphylococcus aureus inoculum sizes: a tripartite in vitro model. BMC Vet Res. 2021 Jan 7;17(1):23. doi: 10.1186/s12917-021-02746-8. PMID: 33413376; PMCID: PMC7792187. 2. Watanabe S, Tsuda M, Terada T, Katsura T, Inui K. Reduced renal clearance of a zwitterionic substrate cephalexin in MATE1-deficient mice. J Pharmacol Exp Ther. 2010 Aug;334(2):651-6. doi: 10.1124/jpet.110.169433. Epub 2010 May 19. PMID: 20484555.

In vivo protocol:

1. Damborg P, Gaustad IB, Olsen JE, Guardabassi L. Selection of CMY-2 producing Escherichia coli in the faecal flora of dogs treated with cephalexin. Vet Microbiol. 2011 Aug 5;151(3-4):404-8. doi: 10.1016/j.vetmic.2011.03.015. Epub 2011 Mar 21. PMID: 21497459.

1: Kanan M, Atif S, Mohammed F, Balahmar Y, Adawi Y, AlSaleem R, Farhan A, Alghoribi M, Mohammed S, Alshanbari R, Fahad M, Kallab R, Mohammed R, Alassaf D, Hazza A. A Systematic Review on the Clinical Pharmacokinetics of Cephalexin in Healthy and Diseased Populations. Antibiotics (Basel). 2023 Sep 3;12(9):1402. doi: 10.3390/antibiotics12091402. PMID: 37760698; PMCID: PMC10526061. 2: Gan A, Delgado L, Swafford K, Brown D, Soneji M. Hemorrhagic Cystitis Due to Cephalexin and Review of the Literature. Clin Pediatr (Phila). 2024 Mar;63(3):423-427. doi: 10.1177/00099228231175473. Epub 2023 May 19. PMID: 37208912; PMCID: PMC10893768. 3: Yu D, Bio LL. Shedding Light on Amoxicillin, Amoxicillin-clavulanate, and Cephalexin Dosing in Children from a Pharmacist's Perspective. J Pediatric Infect Dis Soc. 2022 Dec 28;11(12):594-602. doi: 10.1093/jpids/piac105. PMID: 36112500. 4: Cárdenas Sierra RS, Zúñiga-Benítez H, Peñuela GA. Elimination of cephalexin and doxycycline under low frequency ultrasound. Ultrason Sonochem. 2021 Nov;79:105777. doi: 10.1016/j.ultsonch.2021.105777. Epub 2021 Oct 7. PMID: 34649167; PMCID: PMC8517921. 5: Ali Noman E, Al-Gheethi A, Saphira Radin Mohamed RM, Talip BA, Hossain MS, Ali Hamood Altowayti W, Ismail N. Sustainable approaches for removal of cephalexin antibiotic from non-clinical environments: A critical review. J Hazard Mater. 2021 Sep 5;417:126040. doi: 10.1016/j.jhazmat.2021.126040. Epub 2021 May 8. PMID: 34000703. 6: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Cephalexin. 2021 Jan 18. PMID: 30000547. 7: Nguyen HM, Graber CJ. A Critical Review of Cephalexin and Cefadroxil for the Treatment of Acute Uncomplicated Lower Urinary Tract Infection in the Era of "Bad Bugs, Few Drugs". Int J Antimicrob Agents. 2020 Oct;56(4):106085. doi: 10.1016/j.ijantimicag.2020.106085. Epub 2020 Jul 10. PMID: 32659466. 8: Spelber D, Lahijani S. Neurosyphilis Presenting as Mania and Psychosis After Incidental Treatment With Cephalexin: A Case Report and Literature Review of Jarisch-Herxheimer Reactions. Psychosomatics. 2020 Mar-Apr;61(2):177-180. doi: 10.1016/j.psym.2019.06.001. Epub 2019 Jun 19. PMID: 31331661. 9: Miller LG. Cephalexin plus trimethoprim-sulfamethoxazole was not superior to cephalexin alone for the treatment of outpatient non-purulent cellulitis. Evid Based Med. 2017 Dec;22(6):213. doi: 10.1136/ebmed-2017-110796. Epub 2017 Nov 10. PMID: 29127212. 10: Patel R, Amber KT. Thrombotic thrombocytopenic purpura in a postoperative patient taking cephalexin responding to plasmapheresis: A case report and review of cephalosporin-induced TTP. J Clin Apher. 2016 Oct;31(5):473-5. doi: 10.1002/jca.21420. Epub 2015 Aug 14. PMID: 26274019. 11: McCloskey GL, Massa MC. Cephalexin rash in infectious mononucleosis. Cutis. 1997 May;59(5):251-4. PMID: 9169264. 12: Murray KM, Camp MS. Cephalexin-induced Stevens-Johnson syndrome. Ann Pharmacother. 1992 Oct;26(10):1230-3. doi: 10.1177/106002809202601006. PMID: 1421644. 13: Tanrisever B, Santella PJ. Cefadroxil. A review of its antibacterial, pharmacokinetic and therapeutic properties in comparison with cephalexin and cephradine. Drugs. 1986;32 Suppl 3:1-16. doi: 10.2165/00003495-198600323-00003. PMID: 3542485. 14: Polastri F, Ruffino S, Benech A, Tarello F, Manzon W, Giordano M. Valutazioni sull'impiego della cefalexina monoidrato nella profilassi postoperatoria in chirurgia orale [Evaluation of the use of cephalexin monohydrate in postoperative prophylaxis in oral surgery]. Minerva Stomatol. 1983 Jul-Aug;32(4):617-21. Italian. PMID: 6358852. 15: Jones RN, Preston DA. The antimicrobial activity of cephalexin against old and new pathogens. Postgrad Med J. 1983;59 Suppl 5:9-15. PMID: 6364091. 16: Derrick CW Jr, Reilly K. The role of cephalexin in the treatment of skin and soft-tissue infections. Postgrad Med J. 1983;59 Suppl 5:43-6. PMID: 6364089. 17: Raff MJ. Cephalexin in lower respiratory tract infections. Postgrad Med J. 1983;59 Suppl 5:32-9. PMID: 6364088. 18: Disney FA. Cephalexin in the treatment of upper respiratory tract infections. Postgrad Med J. 1983;59 Suppl 5:28-31. PMID: 6364087. 19: Griffith RS. The pharmacology of cephalexin. Postgrad Med J. 1983;59 Suppl 5:16-27. PMID: 6364086. 20: Speight TM, Brogden RN, Avery GS. Cephalexin: a review of its antibacterial, pharmacological and therapeutic properties. Drugs. 1972;3(1):9-78. doi: 10.2165/00003495-197203010-00002. PMID: 4559812.