cefalexin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 571 15686-71-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefalexin hydrochloride
  • cephalexin
  • cefalexin
  • cephacillin
  • cephalexin anhydrous
  • cephalexin hydrochloride
  • cephalexin hydrate
  • cefalexin HCl
  • cephalexin HCl
A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.
  • Molecular weight: 347.39
  • Formula: C16H17N3O4S
  • CLOGP: -1.84
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 112.73
  • ALOGS: -3.07
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 12 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 91 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 192.00 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.21 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.85 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.57 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 4, 1971 FDA SHIONOGI INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 1125.50 10.75 1117 32970 242708 46409267
Type IV hypersensitivity reaction 182.46 10.75 69 34018 2471 46649504
Cellulitis 118.28 10.75 196 33891 70092 46581883
Injury 113.40 10.75 150 33937 43877 46608098
Urinary tract infection 72.84 10.75 336 33751 219930 46432045
Drug ineffective 67.08 10.75 262 33825 677576 45974399
Emotional distress 58.97 10.75 91 33996 30616 46621359
Loss of employment 58.56 10.75 25 34062 1231 46650744
Rheumatoid arthritis 56.82 10.75 55 34032 240160 46411815
Cholecystitis chronic 55.25 10.75 52 34035 10447 46641528
Deep vein thrombosis 54.11 10.75 154 33933 79619 46572356
Rash maculo-papular 51.29 10.75 81 34006 27793 46624182
Completed suicide 48.38 10.75 23 34064 145897 46506078
Toxicity to various agents 46.11 10.75 52 34035 211714 46440261
Rash 45.05 10.75 427 33660 356085 46295890
Thrombophlebitis superficial 38.96 10.75 31 34056 4972 46647003
Off label use 34.16 10.75 152 33935 379689 46272286
Synovitis 33.52 10.75 3 34084 61072 46590903
Pigment nephropathy 31.46 10.75 6 34081 10 46651965
Oesophageal spasm 31.31 10.75 19 34068 1970 46650005
Uterine perforation 30.82 10.75 32 34055 7235 46644740
Cholelithiasis 29.52 10.75 78 34009 38603 46613372
Intentional overdose 29.04 10.75 6 34081 64938 46587037
Infusion related reaction 26.52 10.75 21 34066 101187 46550788
Anxiety 25.99 10.75 224 33863 181733 46470242
Hepatitis infectious mononucleosis 24.81 10.75 7 34080 96 46651879
Oesophageal pain 24.75 10.75 18 34069 2525 46649450
Gallbladder disorder 24.45 10.75 45 34042 17453 46634522
Cystitis 24.32 10.75 77 34010 42164 46609811
Acute generalised exanthematous pustulosis 24.13 10.75 32 34055 9373 46642602
Agitation neonatal 23.37 10.75 10 34077 495 46651480
Overdose 23.32 10.75 24 34063 101955 46550020
Pemphigus 22.87 10.75 3 34084 45271 46606704
Familial periodic paralysis 22.31 10.75 6 34081 68 46651907
Bronchomalacia 22.31 10.75 7 34080 141 46651834
Chronic kidney disease 22.17 10.75 73 34014 40798 46611177
Joint swelling 22.06 10.75 56 34031 166017 46485958
Therapeutic product effect incomplete 22.05 10.75 15 34072 78138 46573837
Lymphoedema 21.63 10.75 29 34058 8583 46643392
Purpura senile 21.18 10.75 10 34077 625 46651350
Urticaria 21.15 10.75 153 33934 117739 46534236
Anhedonia 20.36 10.75 31 34056 10304 46641671
Poor feeding infant 19.81 10.75 7 34080 206 46651769
Depression 19.57 10.75 200 33887 169904 46482071
Staphylococcal infection 18.61 10.75 63 34024 35708 46616267
Oedema 18.30 10.75 97 33990 66974 46585001
Treatment failure 17.99 10.75 25 34062 93062 46558913
Amniotic cavity infection 17.90 10.75 11 34076 1167 46650808
Tarsal tunnel syndrome 17.89 10.75 9 34078 646 46651329
Vertigo positional 17.76 10.75 15 34072 2615 46649360
Systemic lupus erythematosus 17.74 10.75 13 34074 65167 46586808
Implant site haematoma 17.07 10.75 5 34082 79 46651896
Drug abuse 16.80 10.75 13 34074 63395 46588580
Morbid thoughts 16.45 10.75 8 34079 534 46651441
Vestibular disorder 16.41 10.75 11 34076 1355 46650620
Toxic epidermal necrolysis 16.06 10.75 44 34043 22234 46629741
Hand deformity 15.86 10.75 3 34084 34571 46617404
Scar 15.66 10.75 30 34057 11989 46639986
Coma 15.41 10.75 12 34075 58337 46593638
Multiple lentigines syndrome 15.40 10.75 6 34081 233 46651742
Bronchitis 14.87 10.75 130 33957 105849 46546126
Vanishing bile duct syndrome 14.80 10.75 8 34079 666 46651309
Developmental hip dysplasia 14.62 10.75 10 34077 1273 46650702
Complement factor C4 increased 14.31 10.75 5 34082 142 46651833
Abscess drainage 14.11 10.75 7 34080 488 46651487
Hepatic steatosis 14.00 10.75 44 34043 23998 46627977
Intentional product use issue 13.76 10.75 11 34076 52769 46599206
Delirium 13.72 10.75 5 34082 37223 46614752
Drug interaction 13.40 10.75 90 33997 203004 46448971
Resorption bone increased 13.35 10.75 9 34078 1118 46650857
Rhabdomyolysis 13.28 10.75 7 34080 41902 46610073
Glossodynia 13.22 10.75 8 34079 44365 46607610
Skin infection 13.20 10.75 27 34060 11312 46640663
Immunoglobulins decreased 13.11 10.75 8 34079 838 46651137
Hepatic enzyme increased 12.97 10.75 25 34062 81762 46570213
Therapy interrupted 12.93 10.75 26 34061 10765 46641210
Hyperlipidaemia 12.76 10.75 36 34051 18503 46633472
Blister 12.48 10.75 65 34022 44566 46607409
Breast reconstruction 12.46 10.75 5 34082 210 46651765
Liposuction 12.45 10.75 3 34084 21 46651954
Implant site infection 12.40 10.75 8 34079 923 46651052
Osteolysis 11.98 10.75 12 34075 2600 46649375
Retroperitoneal haematoma 11.87 10.75 12 34075 2628 46649347
Skin ulcer 11.80 10.75 51 34036 32407 46619568
Hypotension 11.67 10.75 111 33976 232478 46419497
Tinea infection 11.65 10.75 8 34079 1024 46650951
Localised infection 11.58 10.75 41 34046 23760 46628215
Ureteric obstruction 11.45 10.75 10 34077 1824 46650151
Drug intolerance 11.35 10.75 62 34025 146987 46504988
Nephrolithiasis 11.31 10.75 51 34036 33000 46618975
Genital ulceration 11.30 10.75 6 34081 482 46651493
Episcleritis 11.27 10.75 7 34080 756 46651219
Diabetic retinal oedema 11.27 10.75 6 34081 485 46651490
Therapeutic response decreased 11.23 10.75 9 34078 43136 46608839
Pulmonary embolism 11.23 10.75 125 33962 108460 46543515
C-reactive protein increased 11.05 10.75 16 34071 58574 46593401
Interstitial lung disease 10.92 10.75 14 34073 53935 46598040
Red man syndrome 10.86 10.75 8 34079 1145 46650830
Idiosyncratic drug reaction 10.76 10.75 7 34080 820 46651155

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 148.64 11.81 187 16538 68332 29867421
Cellulitis 128.35 11.81 144 16581 46640 29889113
Rash 61.22 11.81 240 16485 191649 29744104
Drug tolerance decreased 29.96 11.81 14 16711 1122 29934631
Drug abuse 29.80 11.81 5 16720 82067 29853686
Drug interaction 29.59 11.81 41 16684 199527 29736226
Skin infection 28.10 11.81 25 16700 6119 29929634
Localised infection 27.36 11.81 36 16689 13701 29922052
Venolymphatic malformation 26.62 11.81 6 16719 41 29935712
Pruritus 25.62 11.81 132 16593 118072 29817681
Circumoral oedema 25.57 11.81 6 16719 50 29935703
Urinary tract infection 23.27 11.81 92 16633 73567 29862186
Biliary sepsis 23.21 11.81 10 16715 662 29935091
Toxicity to various agents 22.82 11.81 40 16685 177143 29758610
Perineal abscess 22.40 11.81 7 16718 184 29935569
Renal hypoplasia 22.18 11.81 6 16719 93 29935660
Urticaria 22.16 11.81 74 16651 54532 29881221
Joint swelling 22.14 11.81 67 16658 46879 29888874
Type IV hypersensitivity reaction 20.91 11.81 11 16714 1137 29934616
Clostridium test positive 19.70 11.81 13 16712 2043 29933710
Skin necrosis 19.20 11.81 18 16707 4709 29931044
Gut fermentation syndrome 19.16 11.81 4 16721 18 29935735
Renal tubular necrosis 18.89 11.81 32 16693 15219 29920534
Clostridium difficile colitis 18.83 11.81 29 16696 12739 29923014
Polyomavirus-associated nephropathy 18.77 11.81 15 16710 3170 29932583
Haemorrhoids thrombosed 18.17 11.81 6 16719 189 29935564
Erythema 17.82 11.81 88 16637 77363 29858390
Renal injury 17.81 11.81 27 16698 11702 29924051
Fungal skin infection 17.73 11.81 13 16712 2419 29933334
Mucormycosis 17.55 11.81 18 16707 5250 29930503
Skin lesion 16.86 11.81 34 16691 18460 29917293
Clostridium difficile infection 16.82 11.81 31 16694 15752 29920001
Rash pruritic 16.56 11.81 38 16687 22534 29913219
Arthropathy 16.44 11.81 36 16689 20691 29915062
Neovascular age-related macular degeneration 15.50 11.81 5 16720 146 29935607
Actinic keratosis 15.18 11.81 14 16711 3589 29932164
Libido increased 15.13 11.81 8 16717 836 29934917
Treatment failure 14.96 11.81 48 16677 34631 29901122
Stevens-Johnson syndrome 14.51 11.81 31 16694 17525 29918228
Neonatal disorder 14.43 11.81 8 16717 918 29934835
Factor V inhibition 14.42 11.81 5 16720 183 29935570
Herpes simplex 14.42 11.81 15 16710 4449 29931304
Urethral injury 14.39 11.81 4 16721 69 29935684
Hepatic function abnormal 14.27 11.81 3 16722 41942 29893811
Swollen tongue 14.17 11.81 26 16699 13166 29922587
Arthritis 13.61 11.81 37 16688 24364 29911389
Emotional distress 13.21 11.81 28 16697 15737 29920016
Hypersensitivity vasculitis 12.91 11.81 13 16712 3710 29932043
Retinal degeneration 12.71 11.81 5 16720 262 29935491
Chronic kidney disease 12.54 11.81 48 16677 37790 29897963
Sinusitis 12.48 11.81 44 16681 33301 29902452
Beta haemolytic streptococcal infection 12.45 11.81 6 16719 515 29935238
Off label use 12.36 11.81 85 16640 249205 29686548

Pharmacologic Action:

SourceCodeDescription
ATC J01DB01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
First-generation cephalosporins
FDA CS M0003827 Cephalosporins
FDA EPC N0000175488 Cephalosporin Antibacterial
CHEBI has role CHEBI:36047 antibacterial drugs
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Prostatitis indication 9713002 DOID:14654
Infection of skin AND/OR subcutaneous tissue indication 19824006
Pneumonia due to Streptococcus indication 34020007
Streptococcal tonsillitis indication 41582007
Klebsiella cystitis indication 60867007
Infection of bone indication 111253001
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Streptococcus pyogenes infection indication 302809008
Bacterial urinary infection indication 312124009
Infective otitis media indication 312218008
Infectious disorder of joint indication 363162000
Infection due to Staphylococcus aureus indication 406602003
Osteomyelitis due to Staphylococcus aureus indication 428783003
Klebsiella Prostatitis indication
Proteus Prostatitis indication
Haemophilus Influenzae Acute Otitis Media indication
Streptococcus Osteomyelitis indication
Staphylococcus Acute Otitis Media indication
Moraxella Catarrhalis Acute Otitis Media indication
Bacterial Mastitis off-label use
Prevention of Bacterial Endocarditis off-label use
Diabetic Foot Infection Due to Gram-Positive Bacteria off-label use
Colitis contraindication 64226004 DOID:0060180
Kidney disease contraindication 90708001 DOID:557
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.77 acidic
pKa2 13.53 acidic
pKa3 7.67 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Solute carrier family 15 member 2 Transporter IC50 4.38 WOMBAT-PK
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 3 Enzyme WOMBAT-PK

External reference:

IDSource
4018893 VUID
N0000179741 NUI
D00263 KEGG_DRUG
23325-78-2 SECONDARY_CAS_RN
4018891 VANDF
4018893 VANDF
C0007716 UMLSCUI
CHEBI:3534 CHEBI
CHEMBL1727 ChEMBL_ID
CHEMBL1200544 ChEMBL_ID
CHEMBL1200366 ChEMBL_ID
DB00567 DRUGBANK_ID
D002506 MESH_DESCRIPTOR_UI
27447 PUBCHEM_CID
4832 IUPHAR_LIGAND_ID
2400 INN_ID
OBN7UDS42Y UNII
1299782 RXNORM
4393 MMSL
d00096 MMSL
002716 NDDF
002717 NDDF
387304003 SNOMEDCT_US
54062005 SNOMEDCT_US
54887004 SNOMEDCT_US
785690001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2238 TABLET 250 mg ORAL ANDA 19 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2240 TABLET 500 mg ORAL ANDA 19 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0093-3145 CAPSULE 250 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0093-3147 CAPSULE 500 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0093-4175 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0093-4177 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9769 SUSPENSION 125 mg ORAL ANDA 24 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9770 SUSPENSION 250 mg ORAL ANDA 24 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9897 CAPSULE 500 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9898 CAPSULE 250 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0440-1243 CAPSULE 250 mg ORAL ANDA 19 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 0440-7244 CAPSULE 500 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-004 CAPSULE 500 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-013 CAPSULE 500 mg ORAL ANDA 24 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-020 CAPSULE 500 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-021 CAPSULE 250 mg ORAL ANDA 24 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-025 CAPSULE 500 mg ORAL ANDA 24 sections
cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-057 CAPSULE 500 mg ORAL ANDA 24 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-066 CAPSULE 250 mg ORAL ANDA 19 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-082 CAPSULE 500 mg ORAL ANDA 21 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-142 CAPSULE 250 mg ORAL ANDA 23 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-503 CAPSULE 500 mg ORAL ANDA 13 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-529 CAPSULE 500 mg ORAL ANDA 22 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-617 CAPSULE 500 mg ORAL ANDA 19 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-868 CAPSULE 250 mg ORAL ANDA 21 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-945 CAPSULE 500 mg ORAL ANDA 25 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-946 CAPSULE 250 mg ORAL ANDA 25 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 10544-979 CAPSULE 250 mg ORAL ANDA 22 sections
cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 12634-434 CAPSULE 500 mg ORAL ANDA 20 sections
Cephalexin HUMAN PRESCRIPTION DRUG LABEL 1 15749-801 CAPSULE 250 mg ORAL ANDA 22 sections