Cephalexin

Details

• Internal ID: 7116fcff-dd82-4c6b-a793-a1f6b1cc2995
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• IUPAC 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
• SMILES (Canonical): CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O
• SMILES (Isomeric): CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O
• 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
• InChI Key: ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
• Popularity: 4,686 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇N₃O₄S
• Molecular Weight: 347.40 g/mol
• Exact Mass: 347.09397721 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Cefalexin
• 15686-71-2
• Keflex
• Cephacillin
• Ceporexin
• Cepexin
• Carnosporin
• Cefaleksin
• Cefalexina
• Cefalexine
• Cephalexine
• Cephalexinum
• Mamalexin
• Sinthecillin
• Uphalexin
• Alsporin
• Celexin
• Cepastar
• Ceporex
• Durantel
• Felexin
• Pyassan
• Keflet
• Cefalexinum
• Cefaloto
• Ceporexine
• Cefaseptin
• Lexibiotico
• Madlexin
• Neolexina
• Sencephalin
• Keforal
• Larixin
• Syncl
• Cephalexin anhydrous
• Novolexin
• Biocef
• Panixine Disperdose
• Lilly 66873
• Cefalexin anhydrous
• Anhydrous cephalexin
• 7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanic acid
• Rilexine
• CHEBI:3534
• S 6437
• 7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid
• DTXSID9022780
• 5SFF1W6677
• 7-(D-2-Amino-2-phenylacetamido)-3-methyl-delta3-cephem-4-carboxylic acid
• (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
• NSC-758162
• DTXCID002780
• (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
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-aminophenylacetyl)amino)-3-methyl-8-oxo-, (6R,7R)-
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((aminophenylacetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(R*)))-
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(2-amino-2-phenylacetamido)-3-methyl-8-oxo-, D-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-aminophenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)-
• (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
• Kiflone
• Tenkorex
• Cephalexin USP
• (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
• (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
• RefChem:5657
• Rilexine Chewable Tablets
• (6R,7R)-7-(((2R)-2-azaniumyl-2-phenylacetyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
• Cephalexin Monohydrochloride, Monohydrate
• (6R,7R)-7-((2R)-2-Amino-2-phenylacetylamino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• 239-773-6
• Cefalexin monohydrate
• Cefanex
• LY-66873
• OBN7UDS42Y
• Alcephin
• Cefablan
• Cefadin
• Tepaxin
• Palitrex
• Cefalessina [DCIT]
• Cefalexine [INN-French]
• Cefalexinum [INN-Latin]
• Cefalexina [INN-Spanish]
• Taicelexin
• Cefalexin [INN]
• Ceffanex
• Cephanasten
• CEFADROS
• CEPHAMASTEN
• EFALEXIN
• GARASIN
• IWALEXIN
• KEFLORIDINA
• ORACOCIN
• Ceforal
• Cophalexin
• Factagard
• Kefalospes
• Lopilexin
• Ortisporina
• Sartosona
• Servispor
• Tokiolexin
• Cefadal
• Cefadina
• Cefalin
• Cefovit
• Cephaxin
• Erocetin
• Ibrexin
• Inphalex
• Kefolan
• Kekrinal
• Kidolex
• Lafarine
• Lenocef
• Lonflex
• Mamlexin
• Medoxine
• MFCD00056877
• Oriphex
• Ospexin
• Pectril
• Sanaxin
• Sepexin
• Sialexin
• Sporicef
• Sporidex
• Zozarine
• Alexin
• Cefax
• Cephin
• Cepol
• Check
• Fexin
• Ibilex
• Neokef
• Nufex
• Oracef
• Oroxin
• Roceph
• Syncle
• Synecl
• Voxxim
• Winlex
• Cefa-iskia
• Ceporex Forte
• Ceporexin-E
• SQ 20248
• CHEMBL1727
• Durantel DS
• L-Keflex
• Cefalessina
• CEX
• Ed A-Ceph
• LILLY-66873
• Roceph Distab
• NCGC00159522-02
• Ceflax
• S-6437
• (6R,7R)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Cephalexin 1-hydrate
• Cerexin
• Optocef
• Cephalexin [USAN:BAN]
• (6R,7R)-7-((R)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• SMR000338536
• CAS-15686-71-2
• Keflex (TN)
• HSDB 3022
• EINECS 239-773-6
• BRN 0965503
• Cerexins
• Amplex
• UNII-5SFF1W6677
• Anhydrous cefalexin
• (6R,7R)-7-((R)-2-AMINO-2-PHENYLACETAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
• Cefalexin (JP18)
• Cephalexin (Standard)
• Cephalexin (Cefalexin)
• CEFALEXIN [JAN]
• CEPHALEXIN [MI]
• Prestwick0_000358
• Prestwick1_000358
• Prestwick2_000358
• Prestwick3_000358
• CEPHALEXIN [HSDB]
• Epitope ID:117132
• CEFALEXIN [WHO-DD]
• SCHEMBL2961
• 7-(D-2-Amino-2-phenylacetamido)-3-methyl-delta (sup 3)-cephem-4- carboxylic acid
• BSPBio_000455
• (6R,7R)-7-((R)-2-Amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
• MLS000759527
• MLS001424036
• SPBio_002376
• BPBio1_000501
• GTPL4832
• orb1310065
• HY-B0200R
• MSK7013
• BCPP000289
• HMS2051A04
• HY-B0200
• Tox21_111740
• BDBM50139896
• AKOS004119846
• Tox21_111740_1
• BCP9000509
• CCG-100831
• CS-2137
• DB00567
• NC00081
• NSC 758162
• NCGC00159522-03
• NCGC00159522-05
• DS-11971
• NS00098606
• Cefalexin, VETRANAL(TM), analytical standard
• C06895
• D00263
• H10995
• Cefalexin 1000 microg/mL in Acetonitrile:Water
• Q411417
• BRD-K90733503-001-05-3
• BRD-K90733503-001-06-1
• BRD-K90733503-001-07-9
• BRD-K90733503-002-03-6
• Cefalexin, British Pharmacopoeia (BP) Reference Standard
• Z1880962282
• 7-(D-alpha-amino-phenylacetamido)-3-methyl-3-cepheme-4-carboxylic acid
• Cephalexin, Pharmaceutical Secondary Standard; Certified Reference Material
• 7-(D-.ALPHA.-AMINO-.ALPHA.-PHENYLACETAMIDO)-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID
• 7beta-[(2R)-2-amino-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic acid
• (6R,7R)-7-((R)-2-Amino-2-phenyl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-7-((R)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINOPHENYLACETYL)AMINO)-3-METHYL-8-OXO-,(6R-(6.ALPHA.,7.BETA.(R*)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8038	80.38%
Caco-2	-	0.8840	88.40%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.9857	98.57%
Subcellular localzation	Mitochondria	0.4732	47.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9446	94.46%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7174	71.74%
P-glycoprotein inhibitior	-	0.9062	90.62%
P-glycoprotein substrate	-	0.9168	91.68%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8614	86.14%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9251	92.51%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.9242	92.42%
CYP2C8 inhibition	-	0.9883	98.83%
CYP inhibitory promiscuity	-	0.9303	93.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8726	87.26%
Carcinogenicity (trinary)	Non-required	0.5826	58.26%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9866	98.66%
Skin irritation	-	0.7531	75.31%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.9735	97.35%
skin sensitisation	-	0.9077	90.77%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.7294	72.94%
Acute Oral Toxicity (c)	IV	0.6641	66.41%
Estrogen receptor binding	-	0.4860	48.60%
Androgen receptor binding	-	0.6254	62.54%
Thyroid receptor binding	-	0.6525	65.25%
Glucocorticoid receptor binding	-	0.7063	70.63%
Aromatase binding	+	0.5782	57.82%
PPAR gamma	-	0.5804	58.04%
Honey bee toxicity	-	0.9194	91.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9677	96.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	112.2 nM	Potency	via Super-PRED
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	25.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.46%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.02%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.57%	93.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.88%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.39%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.52%	93.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.39%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	84.68%	91.19%
CHEMBL220	P22303	Acetylcholinesterase	83.59%	94.45%
CHEMBL5028	O14672	ADAM10	83.49%	97.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.05%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.91%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 27447
• NPASS: NPC13470
• ChEMBL: CHEMBL1727
• LOTUS: LTS0267481
• wikiData: Q411417