Dicloxacillin (CED0006121)

Record Information

Version

1.0

Creation Date

2016-05-25 18:20:42 UTC

Update Date

2026-08-20 02:12:33 UTC

Accession Number

CHEM022116

Identification

Common Name

Dicloxacillin

Class

Small Molecule

Description

Dicloxacillin is an organic compound with the chemical formula C19H17Cl2N3O5S and an average molecular weight of 470.33 g/mol. Dicloxacillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is found in or released from four recorded sources, including drinking water and water supply (drinking water), electrical and electronic equipment (antennas), and healthcare, pharmaceuticals and veterinary products specifically within the categories of penicillins and antibiotics. Recorded exposure routes for the substance include oral and inhalation. In terms of biological activity, there are five recorded protein targets for dicloxacillin. It acts as an inhibitor of Penicillin-binding protein 1b (pbp1b), Penicillin-binding protein 2a (pbp2a), Penicillin-binding protein 1A (pbpA), and serine-type D-Ala-D-Ala carboxypeptidase (pbp3), as well as one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
Dicloxacilina	ChEBI
Dicloxacilline	ChEBI
Dicloxacillinum	ChEBI
(2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
Diclossacillina	HMDB
Dicloxacilin	HMDB
Dicloxacycline	HMDB
Bristol myers squibb brand OF dicloxacillin sodium	HMDB
Dicloxaciclin	HMDB
Dicloxacillin, monosodium salt, mono-hydrate	HMDB
Posipen	HMDB
Sanfer brand OF dicloxacillin sodium	HMDB
Sigma brand OF dicloxacillin sodium	HMDB
Sodium, dicloxacillin	HMDB
Alphapharm brand OF dicloxacillin sodium	HMDB
Antibioticos brand OF dicloxacillin sodium	HMDB
Cilpen	HMDB
Diclocil	HMDB
Ditterolina	HMDB
Dynapen	HMDB
Infectopharm brand OF dicloxacillin sodium	HMDB
Bristol-myers squibb brand OF dicloxacillin sodium	HMDB
Dichloroxacillin	HMDB
Dicloxsig	HMDB
Distaph	HMDB
Geneva brand OF dicloxacillin sodium	HMDB
InfectoStaph	HMDB
Pathocil	HMDB
SmithKline beecham brand OF dicloxacillin sodium	HMDB
Dicloxacillin sodium	HMDB
Dicloxacillin, monosodium salt, anhydrous	HMDB
Dycill	HMDB
Fustery brand OF dicloxacillin sodium	HMDB
Wyeth brand OF dicloxacillin sodium	HMDB

Chemical Formula

C₁₉H₁₇Cl₂N₃O₅S

Average Molecular Mass

470.326 g/mol

Monoisotopic Mass

469.027 g/mol

CAS Registry Number

3116-76-5

IUPAC Name

(2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

dicloxacillin

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl)C(O)=O

InChI Identifier

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

InChI Key

YFAGHNZHGGCZAX-JKIFEVAISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Penam
1,3-dichlorobenzene
Halobenzene
Chlorobenzene
Aryl chloride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Azole
Isoxazole
Thiazolidine
Tertiary carboxylic acid amide
Beta-lactam
Heteroaromatic compound
Azetidine
Lactam
Carboxamide group
Oxacycle
Carboximidic acid
Carboximidic acid derivative
Azacycle
Carboxylic acid
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hemithioaminal
Monocarboxylic acid or derivatives
Thioether
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dichlorobenzene (CHEBI:4511 )
penicillin (CHEBI:4511 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.19	ALOGPS
logP	2.91	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-0.71	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.44 m³·mol⁻¹	ChemAxon
Polarizability	42.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-9323100000-c8806eaea476ee681443	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-9101010000-09418080881eaa1e2c3d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1926600000-2819aa19376902b7bbc1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-2963100000-d32486357adcfc7196e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0900-4950000000-26919912afad41b9ef63	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009100000-eb6339e06bab6641dd24	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0059100000-aef2e49cd1687d6bd205	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-2953000000-61a1b22f6ec123b74f59	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0040900000-ed5127e8aa95abd525e7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066u-5191200000-690169527ca40b9acb24	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9160000000-b06f78c610c2164b8256	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0110900000-9f1adb53dd2f402534ae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w90-0692400000-1b61e8c8f12f22e71248	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2690000000-1f0f86be139885db99f1	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5840.0	Log mg/kg	[3300:10000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
340	Penicillins	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

2 pathways

Dicloxacillin Drug Metabolism Action Pathway

Dicloxacillin Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	0.0778492
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	0.0778492
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	0.0778492
Click to view 3D structure	Nucleoprotein	P15682	Influenza A virus (strain A/Wilson-Smith/1933 H1N1)	Predicted (SEA)	1.86838
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	70.1422
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	86.8797
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	50.9134
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase 13	Q7Z5P4	Humans	Predicted (SEA)	13.4679
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	121.523
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	82.0531
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	73.4897
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	49.5121
Click to view 3D structure	Vitamin D3 receptor	P11473	Humans	Predicted (SEA)	62.8243
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	404.582
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	243.746
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	209.804
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	316.457
Click to view 3D structure	Retinoic acid receptor gamma	P13631	Humans	Predicted (SEA)	44.9968
Click to view 3D structure	Retinoic acid receptor alpha	P10276	Humans	Predicted (SEA)	47.9551
Click to view 3D structure	Leukemia inhibitory factor receptor	P42702	Humans	Predicted (SEA)	26.0016
Click to view 3D structure	Fatty acid-binding protein, liver	P07148	Humans	Predicted (SEA)	19.1509
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	3804.26
Click to view 3D structure	Beta-lactamase	P00811	Escherichia coli (strain K12)	Predicted (SEA)	8.64126
Click to view 3D structure	Oxysterols receptor LXR-alpha	Q13133	Humans	Predicted (SEA)	152.818
Click to view 3D structure	Oxysterols receptor LXR-beta	P55055	Humans	Predicted (SEA)	122.301