Cephalexin

Identification

Summary

Cephalexin is a first generation cephalosporin used to treat certain susceptible bacterial infections.

Brand Names

Keflex

Generic Name

Cephalexin

DrugBank Accession Number

DB00567

Background

Cephalexin is the first of the first generation cephalosporins.^7,8 This antibiotic contains a beta lactam and a dihydrothiazide.⁷ Cephalexin is used to treat a number of susceptible bacterial infections through inhibition of cell wall synthesis.^9,Label Cephalexin was approved by the FDA on 4 January 1971.¹²

Type

Small Molecule

Groups

Approved, Investigational, Vet approved

Structure

Similar Structures

Weight: Average: 347.389
Monoisotopic: 347.093976737
Chemical Formula: C₁₆H₁₇N₃O₄S

Synonyms

(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
7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanic acid
7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid
Anhydrous cefalexin
Anhydrous cephalexin
Cefalexin
Cefalexin anhydrous
Cefalexina
Céfalexine
Cefalexinum
Cephalexin anhydrous

External IDs

LILLY-66873
S-6437

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Pharmacology

Indication

Cephalexin is indicated for the treatment of certain infections caused by susceptible bacteria.^Label,13,14 These infections include respiratory tract infections, otitis media, skin and skin structure infections, bone infections, and genitourinary tract infections.^Label,13,14

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Associated Conditions

Indication Type	Indication	Approval Level
Treatment of	Bone infection	••••••••••••
Treatment of	Genitourinary tract infection	••••••••••••
Treatment of	Otitis media	••••••••••••
Treatment of	Respiratory tract infection	••••••••••••
Treatment of	Respiratory tract infections	••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic.^7,8 It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations.^Label It is effective against most gram-positive bacteria through its inihibition of the cross linking reaction between N-acetyl muramicacid and N-acetylglucosamine in the cell wall, leading to cell lysis.⁹

Mechanism of action

Cephalexin is a first generation cephalosporin antibiotic.^7,8 Cephalosporins contain a beta lactam and dihydrothiazide.⁷ Unlike penicillins, cephalosprins are more resistant to the action of beta lactamase.⁷ Cephalexin inhibits bacterial cell wall synthesis, leading breakdown and eventualy cell death.^Label

Target	Actions	Organism
APenicillin-binding protein 3	inhibitor	Streptococcus pneumoniae
APenicillin-binding protein 2a	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1b	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1A	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Absorption

Well absorbed from the upper gastrointestinal tract with nearly 100% oral bioavailability.^3,4 Cephalexin is not absorbed in the stomach but is absorbed in the upper intestine.⁵

Patients taking 250mg of cephalexin reach a maximum plasma concentration of 7.7mcg/mL and patients taking 500mg reach 12.3mcg/mL.¹

Volume of distribution

5.2-5.8L.⁶

Protein binding

Cephalexin is 10-15% bound to serum proteins^Label,13 including serum albumin.¹⁰

Metabolism

Cephalexin is not metabolized in the body.^{2,Label,13,14}

Route of elimination

Cephalexin is over 90% excreted in the urine after 6 hours¹ by glomerular filtration and tubular secretion^Label,13,14 with a mean urinary recovery of 99.3%.³ Cephalexin is unchanged in the urine.^1,2,3

Half-life

The half life of cephalexin is 49.5 minutes in a fasted state and 76.5 minutes with food though these times were not significantly different in the study.³

Clearance

Clearance from one subject was 376mL/min.³

Adverse Effects

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Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.^Label An overdose is generally managed through supportive treatment as diuresis, dialysis, hemodialysis, and charcoal hemoperfusion are not well studied in this case.^Label

The oral median lethal dose of cephalexin in rats is >5000 mg/kg. The oral LD50 in a monkey is >1g/kg and the lowest dose causing a toxic effect in humans is 14mg/kg.^MSDS

Cephalexin has not been shown to be harmful in pregnancy and is not associated with teratogeniticy.^Label Cephalexin is present in breast milk, though infants may be exposed to <1% of the dose given to the mother.^Label The effects of breast milk exposure to cephalexin have not been established and so caution must be exercised and the risk and benefit of cephalexin use in breastfeeding must be weighed.^Label

Cephalexin has not been studied for carcinogenicity or mutagenicity.^Label Cephalexin has no affect on fertility in rats.^Label

Pathways

Not Available

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Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Cephalexin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Cephalexin can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Cephalexin can be increased when combined with Abatacept.
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Cephalexin.
Abemaciclib	The excretion of Abemaciclib can be decreased when combined with Cephalexin.

Food Interactions

Take with or without food.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Cefalexin hydrochloride	6VJE5G3D98	105879-42-3	YHJDZIQOCSDIQU-OEDJVVDHSA-N
Cefalexin monohydrate	OBN7UDS42Y	23325-78-2	AVGYWQBCYZHHPN-CYJZLJNKSA-N
Cefalexin sodium	F78YJG0WXK	38932-40-0	NZDYPHVJLWMLJI-CYJZLJNKSA-M

Product Images

International/Other Brands

Alcephin (Alembic) / Alexin (Dabur) / Alsporin (Renata) / Cefadin (Life) / Cefalin (BioFemme) / Ceforal (Teva) / Cefovit (Vitamed) / Celexin (Atlantic) / Cephin (General Drugs House) / Ceporexin (Investi) / Felexin (Remedica) / Ibilex (Alphapharm) / Keforal (Saiph) / L-Keflex (Shionogi Seiyaku) / Larixin (Taisho Yakuhin) / Lonflex (Union) / Madlexin (Meiji) / Nufex (General Pharma) / Oriphex (Maydsm Trading) / Ospexin (Sandoz) / Palitrex (Galenika) / Pyassan (Sanofi) / Sanaxin (Sandoz) / Sencephalin (Takeda Pharmaceutical) / Sepexin (Hetero) / Servispor (Sandoz) / Sialexin (Siam Bheasach) / Sporicef (Ranbaxy) / Sporidex (Ranbaxy) / Syncl (Asahi Kasei Pharma) / Tepaxin (Takeda) / Uphalexin (CCM) / Voxxim (Roddensers) / Winlex (Winston)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Asn-cephalexin	Powder, for suspension	125 mg / 5 mL	Oral	Ascend Laboratories Ltd	Not applicable	Not applicable
Asn-cephalexin	Powder, for suspension	250 mg / 5 mL	Oral	Ascend Laboratories Ltd	Not applicable	Not applicable
Cephalexin	Capsule	750 mg/1	Oral	Fera Pharmaceuticals, LLC	2017-06-02	2021-12-31
Cephalexin	Tablet	500 mg	Oral	Sanis Health Inc	2022-05-31	Not applicable
Cephalexin	Tablet	250 mg	Oral	Sanis Health Inc	2022-05-31	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-cephalex	Tablet	250 mg	Oral	Apotex Corporation	1988-12-31	Not applicable
Apo-cephalex	Tablet	500 mg	Oral	Apotex Corporation	1988-12-31	Not applicable
Auro-cephalexin	Powder, for suspension	125 mg / 5 mL	Oral	Auro Pharma Inc	2020-07-23	Not applicable
Auro-cephalexin	Tablet	250 mg	Oral	Auro Pharma Inc	2018-07-30	Not applicable
Auro-cephalexin	Powder, for suspension	250 mg / 5 mL	Oral	Auro Pharma Inc	2020-07-23	Not applicable

Chemical Identifiers

UNII: 5SFF1W6677
CAS number: 15686-71-2
InChI Key: ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
InChI: 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)/t10-,11-,15-/m1/s1
IUPAC Name: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES: [H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O

References

Synthesis Reference

Peter Faarup, "Method of preparing a sparingly soluble complex of cephalexin." U.S. Patent US4003896, issued May, 1975.

US4003896

General References

Thornhill TS, Levison ME, Johnson WD, Kaye D: In vitro antimicrobial activity and human pharmacology of cephalexin, a new orally absorbed cephalosporin C antibiotic. Appl Microbiol. 1969 Mar;17(3):457-61. [Article]
Sullivan HR, Billings RE, McMahon RE: Metabolism of cephalexin-14C in mice and in rats. J Antibiot (Tokyo). 1969 May;22(5):195-200. [Article]
Gower PE, Dash CH: Cephalexin: human studies of absorption and excretion of a new cephalosporin antibiotic. Br J Pharmacol. 1969 Nov;37(3):738-47. doi: 10.1111/j.1476-5381.1969.tb08513.x. [Article]
Henning C, Kallings LO, Lidman K, Sterner G: Studies of absorption, excretion, antibacterial and clinical effect of cephalexin. Scand J Infect Dis. 1970;2(2):131-8. [Article]
Griffith RS: The pharmacology of cephalexin. Postgrad Med J. 1983;59 Suppl 5:16-27. [Article]
Pfeffer M, Jackson A, Ximenes J, de Menezes JP: Comparative human oral clinical pharmacology of cefadroxil, cephalexin, and cephradine. Antimicrob Agents Chemother. 1977 Feb;11(2):331-8. doi: 10.1128/aac.11.2.331. [Article]
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. [Article]
Sader HS, Jacobs MR, Fritsche TR: Review of the spectrum and potency of orally administered cephalosporins and amoxicillin/clavulanate. Diagn Microbiol Infect Dis. 2007 Mar;57(3 Suppl):5S-12S. doi: 10.1016/j.diagmicrobio.2006.12.014. Epub 2007 Feb 9. [Article]
Fisher JF, Meroueh SO, Mobashery S: Bacterial resistance to beta-lactam antibiotics: compelling opportunism, compelling opportunity. Chem Rev. 2005 Feb;105(2):395-424. doi: 10.1021/cr030102i. [Article]
Nerli B, Romanini D, Pico G: Structural specificity requirements in the binding of beta lactam antibiotics to human serum albumin. Chem Biol Interact. 1997 May 2;104(2-3):179-202. [Article]
Cephalexin Product Monograph [Link]
FDA Approved Drug Products: Cephalexin Oral Capsule [Link]
FDA Approved Drug Products: Cephalexin Oral Suspension [Link]
FDA Approved Drug Products: Cephalexin Oral Tablet [Link]

External Links

Human Metabolome Database: HMDB0014707
KEGG Drug: D00263
KEGG Compound: C06895
PubChem Compound: 27447
PubChem Substance: 46506749
ChemSpider: 25541
BindingDB: 50139896
RxNav: 1299782
ChEBI: 3534
ChEMBL: CHEMBL1727
ZINC: ZINC000003830500
Therapeutic Targets Database: DAP000437
PharmGKB: PA448883
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Cefalexin

FDA label

Download (133 KB)

MSDS

Download (25.4 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Arrhythmia	2
4	Completed	Prevention	Urinary Tract Infections, Recurrent	1
4	Completed	Treatment	Abscesses / Folliculitis / Infection caused by staphylococci / Staphylococcal Skin Infections	1
4	Completed	Treatment	Cellulitis	1
4	Completed	Treatment	Clean Laceration / Hand Laceration / No Bone Involved / Tendon Involved	1

Pharmacoeconomics

Manufacturers

Acs dobfar info sa
Apothecon inc div bristol myers squibb
Aurobindo pharma ltd inc
Barr laboratories inc
Belcher pharmaceuticals inc
Hikma pharmaceuticals
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Lupin ltd
Orchid healthcare
Purepac pharmaceutical co
Ranbaxy laboratories ltd
Jerome stevens pharmaceuticals inc
Sun pharmaceutical industries ltd
Teva pharmaceuticals usa inc
Yoshitomi pharmaceutical industries ltd
Yung shin pharmaceutical industrial co ltd
Middlebrook pharmaceuticals inc
Vitarine pharmaceuticals inc
Lex pharmaceuticals inc
Eli lilly and co

Packagers

Advanced Pharmaceutical Services Inc.
Aidarex Pharmacuticals LLC
Altura Pharmaceuticals Inc.
Amkas Laboratories Inc.
A-S Medication Solutions LLC
Aurobindo Pharma Ltd.
Bryant Ranch Prepack
Cardinal Health
Carlisle Laboratories Inc.
Carlsbad Technology Inc.
Central Texas Community Health Centers
Ceph International Corp.
Comprehensive Consultant Services Inc.
Darby Dental Supply Co. Inc.
DAVA Pharmaceuticals
Dispensing Solutions
Diversified Healthcare Services Inc.
Dorx LLC
Eli Lilly & Co.
Gen Source Rx
Golden State Medical Supply Inc.
H.J. Harkins Co. Inc.
Innoviant Pharmacy Inc.
Institut Biochemique SA
International Ethical Labs Inc.
Jazeera Pharmaceutical Industries
Keltman Pharmaceuticals Inc.
Levista Inc.
Liberty Pharmaceuticals
Lupin Pharmaceuticals Inc.
Major Pharmaceuticals
Medvantx Inc.
Middlebrook Pharmaceuticals
Murfreesboro Pharmaceutical Nursing Supply
Northstar Rx LLC
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Patheon Inc.
Patient First Corp.
PD-Rx Pharmaceuticals Inc.
Pharmaceutical Utilization Management Program VA Inc.
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Prescript Pharmaceuticals
Qualitest
Ranbaxy Laboratories
Rebel Distributors Corp.
Redpharm Drug
Stat Rx Usa
Stat Scripts LLC
Sun Pharmaceutical Industries Ltd.
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Vedco Inc.
West-Ward Pharmaceuticals
World Gen LLC
Yung Shin Pharmaceutical Industry Ltd.

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral	1 g
Capsule	Oral	500.000 mg
Suspension
Tablet	Oral
Syrup	Oral
Suspension	Oral
Tablet	Oral	526.04 mg
Capsule, coated	Oral	500 mg
Capsule, coated	Oral	525.76 mg
Powder, for suspension	Oral	2.5 g
Suspension	Oral	5 g
Tablet	Oral	1 mg
Powder, for solution	Oral	5.2576 g
Tablet	Oral	500.000 mg
Powder, for suspension	Oral
Capsule, coated	Oral	50000000 mg
Capsule	Oral	250.000 mg
Granule, for suspension	Oral	125 mg/5ml
Tablet, film coated	Oral	1000 MG
For suspension	Oral	125 mg/5mL
For suspension	Oral	250 mg/5mL
Powder, for suspension	Oral	125 mg/5mL
Powder, for suspension	Oral	250 mg/5mL
Tablet	Oral	250 mg/1
Tablet	Oral	500 mg/1
Suspension	Oral	125 mg/5mL
Suspension	Oral	250 mg/5mL
Tablet, film coated	Oral
Capsule	Oral	250 MG
Suspension	Oral	5 %
Syrup	Oral	10 %
Syrup	Oral	5 %
Tablet	Oral	1 g
Tablet	Oral	1.000 g
Tablet, coated	Oral	1 G
Powder, for suspension	Oral	250 mg
Capsule, coated	Oral	250 mg
Powder, for solution	Oral	500000 g
Powder, for suspension	Oral	5300 mg/100ml
Capsule	Oral	250 mg/1
Capsule	Oral	333 mg/1
Capsule	Oral	500 mg/1
Capsule	Oral	750 mg/1
Granule, for suspension	Oral
Powder, for suspension	Oral	125 mg / 5 mL
Powder, for suspension	Oral	250 mg / 5 mL
Tablet, coated	Oral	1000 mg
Tablet, film coated	Oral	500 mg
Solution / drops	Oral	100 MG/ML
Powder, for suspension	Oral	5 g
Tablet, film coated	Oral	1 gr
Capsule	Oral
Suspension	Oral
Suspension	Oral	5.000 g
Suspension	Oral	2.500 g
Tablet	Oral	250 mg
Tablet	Oral	500 mg
Capsule	Oral
Granule, for suspension	Oral	250 mg/5ml
Tablet	Oral	1000 mg
Granule	Oral	276.03 mg
Granule	Oral	5 g
Capsule, coated	Oral	0.5 g
Tablet, soluble	Oral	125 mg/1
Tablet, soluble	Oral	250 mg/1
Tablet	Oral
Suspension	Oral	125 mg / 5 mL
Suspension	Oral	250 mg / 5 mL
Powder		250 mg/5ml
Tablet, extended release	Oral	750 mg
Tablet, film coated	Oral	250 mg
Tablet, coated	Oral	500 mg
Tablet, coated	Oral	250 mg
Powder, for suspension	Oral	500 mg/5ml
Capsule	Oral	500 mg

Prices

Unit description	Cost	Unit
Cephalexin 250 mg/5ml Suspension 200ml Bottle	32.76USD	bottle
Cephalexin 250 mg/5ml Suspension 100ml Bottle	19.66USD	bottle
Cephalexin 125 mg/5ml Suspension 200ml Bottle	16.39USD	bottle
Cephalexin 125 mg/5ml Suspension 100ml Bottle	15.99USD	bottle
Keflex 500 mg capsule	5.75USD	capsule
Keflex 500 mg pulvule	4.99USD	each
Keflex 750 mg capsule	3.34USD	capsule
Cephalexin 500 mg tablet	2.25USD	tablet
Keflex 250 mg capsule	2.2USD	capsule
Keflex 250 mg pulvule	1.85USD	each
Cephalexin 500 mg capsule	1.4USD	capsule
Cephalexin 250 mg tablet	1.17USD	tablet
Cephalexin 250 mg capsule	0.72USD	capsule
Apo-Cephalex 500 mg Tablet	0.47USD	tablet
Novo-Lexin 500 mg Capsule	0.47USD	capsule
Novo-Lexin 500 mg Tablet	0.47USD	tablet
Nu-Cephalex 500 mg Tablet	0.47USD	tablet
Apo-Cephalex 250 mg Tablet	0.24USD	tablet
Novo-Lexin 250 mg Capsule	0.24USD	capsule
Novo-Lexin 250 mg Tablet	0.24USD	tablet
Nu-Cephalex 250 mg Tablet	0.24USD	tablet
Novo-Lexin 50 mg/ml Suspension	0.14USD	ml
Novo-Lexin 25 mg/ml Suspension	0.09USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	326.8 °C	http://www.chemspider.com/Chemical-Structure.25541.html
boiling point (°C)	727.4	http://www.chemspider.com/Chemical-Structure.25541.html
water solubility	10mg/mL	http://www.chemspider.com/Chemical-Structure.25541.html
logP	0.65	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.297 mg/mL	ALOGPS
logP	0.55	ALOGPS
logP	-2.1	Chemaxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.26	Chemaxon
pKa (Strongest Basic)	7.23	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	112.73 Å²	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	88.97 m³·mol^-1	Chemaxon
Polarizability	32.52 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.7537
Blood Brain Barrier	-	0.996
Caco-2 permeable	-	0.8956
P-glycoprotein substrate	Substrate	0.786
P-glycoprotein inhibitor I	Non-inhibitor	0.9033
P-glycoprotein inhibitor II	Non-inhibitor	0.9921
Renal organic cation transporter	Non-inhibitor	0.9485
CYP450 2C9 substrate	Non-substrate	0.8011
CYP450 2D6 substrate	Non-substrate	0.8308
CYP450 3A4 substrate	Non-substrate	0.5289
CYP450 1A2 substrate	Non-inhibitor	0.9242
CYP450 2C9 inhibitor	Non-inhibitor	0.9251
CYP450 2D6 inhibitor	Non-inhibitor	0.9359
CYP450 2C19 inhibitor	Non-inhibitor	0.922
CYP450 3A4 inhibitor	Non-inhibitor	0.831
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9303
Ames test	Non AMES toxic	0.6834
Carcinogenicity	Non-carcinogens	0.8861
Biodegradation	Not ready biodegradable	0.9812
Rat acute toxicity	1.2715 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9971
hERG inhibition (predictor II)	Non-inhibitor	0.8686

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-0900000000-268bac07b4777b149217
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0ab9-0900000000-e1976a2fc84f1a3ef783
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-053s-0904000000-31572235000f1be84e04
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001r-4922000000-f91e593d765e1ee6f381
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1930000000-b993c679de8cad6c6a87
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1945000000-a1c3d53b3bf453dca01c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1921000000-58cd0524920e8ad40125
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0zfu-5920000000-df6deb0a1e4cc6c3b9a4
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	181.5579472	predicted	DarkChem Lite v0.1.0
[M-H]-	182.1370472	predicted	DarkChem Lite v0.1.0
[M-H]-	177.76091	predicted	DeepCCS 1.0 (2019)
[M+H]+	180.9790472	predicted	DarkChem Lite v0.1.0
[M+H]+	181.0009472	predicted	DarkChem Lite v0.1.0
[M+H]+	180.11891	predicted	DeepCCS 1.0 (2019)
[M+Na]+	180.6759472	predicted	DarkChem Lite v0.1.0
[M+Na]+	186.81802	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Penicillin-binding protein 3

Kind: Protein
Organism: Streptococcus pneumoniae
Pharmacological action: Yes
Actions: Inhibitor

General Function: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function: Not Available
Gene Name: pbp3
Uniprot ID: Q75Y35
Uniprot Name: Penicillin-binding protein 3
Molecular Weight: 45209.84 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]

Details2. Penicillin-binding protein 2a

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Transferase activity, transferring acyl groups
Specific Function: Not Available
Gene Name: pbp2a
Uniprot ID: Q8DNB6
Uniprot Name: Penicillin-binding protein 2a
Molecular Weight: 80797.94 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
Mitsuoka K, Kato Y, Kubo Y, Tsuji A: Functional expression of stereoselective metabolism of cephalexin by exogenous transfection of oligopeptide transporter PEPT1. Drug Metab Dispos. 2007 Mar;35(3):356-62. Epub 2006 Dec 1. [Article]

Details3. Penicillin-binding protein 1b

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Transferase activity, transferring acyl groups
Specific Function: Not Available
Gene Name: pbp1b
Uniprot ID: Q7CRA4
Uniprot Name: Penicillin-binding protein 1b
Molecular Weight: 89479.92 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]

Details4. Penicillin-binding protein 2B

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Not Available
Specific Function: Penicillin binding
Gene Name: penA
Uniprot ID: P0A3M6
Uniprot Name: Penicillin-binding protein 2B
Molecular Weight: 73872.305 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]

Details5. Penicillin-binding protein 1A

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Penicillin binding
Specific Function: Cell wall formation.
Gene Name: pbpA
Uniprot ID: Q8DR59
Uniprot Name: Penicillin-binding protein 1A
Molecular Weight: 79700.9 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
Nerli B, Romanini D, Pico G: Structural specificity requirements in the binding of beta lactam antibiotics to human serum albumin. Chem Biol Interact. 1997 May 2;104(2-3):179-202. [Article]

Transporters

Details1. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	13700000	N/A	N/A	A16247
Ki (nM)	14400000	N/A	N/A	A16239
Ki (nM)	14000000	N/A	N/A	A18341

Details2. Solute carrier family 15 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name: SLC15A1
Uniprot ID: P46059
Uniprot Name: Solute carrier family 15 member 1
Molecular Weight: 78805.265 Da

References

Liang R, Fei YJ, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH: Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization. J Biol Chem. 1995 Mar 24;270(12):6456-63. [Article]
Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [Article]
Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [Article]
Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [Article]
Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [Article]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [Article]
Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A: The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine. J Pharm Pharmacol. 1997 Aug;49(8):796-801. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	75000	N/A	N/A	A18355

Details3. Solute carrier family 15 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Peptide:proton symporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name: SLC15A2
Uniprot ID: Q16348
Uniprot Name: Solute carrier family 15 member 2
Molecular Weight: 81782.77 Da

References

Liu W, Liang R, Ramamoorthy S, Fei YJ, Ganapathy ME, Hediger MA, Ganapathy V, Leibach FH: Molecular cloning of PEPT 2, a new member of the H+/peptide cotransporter family, from human kidney. Biochim Biophys Acta. 1995 May 4;1235(2):461-6. [Article]
Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [Article]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]

Details4. Solute carrier family 22 member 6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name: SLC22A6
Uniprot ID: Q4U2R8
Uniprot Name: Solute carrier family 22 member 6
Molecular Weight: 61815.78 Da

References

Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [Article]

Details5. Multidrug and toxin extrusion protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Monovalent cation:proton antiporter activity
Specific Function: Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name: SLC47A1
Uniprot ID: Q96FL8
Uniprot Name: Multidrug and toxin extrusion protein 1
Molecular Weight: 61921.585 Da

References

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. [Article]
Motohashi H, Inui K: Organic cation transporter OCTs (SLC22) and MATEs (SLC47) in the human kidney. AAPS J. 2013 Apr;15(2):581-8. doi: 10.1208/s12248-013-9465-7. Epub 2013 Feb 22. [Article]

Details6. Solute carrier family 22 member 8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name: SLC22A8
Uniprot ID: Q8TCC7
Uniprot Name: Solute carrier family 22 member 8
Molecular Weight: 59855.585 Da

References

Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Cephalexin

Identification

Structure for Cephalexin (DB00567)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

References

Carriers

References

Transporters

References

References

References

References

References

References