Details of the Drug

General Information of Drug (ID: DM8EU0Z)

Drug Name

Dicloxacillin

Synonyms

Dichloroxacillin; Diclossacillina; Dicloxaciclin; Dicloxacilin; Dicloxacilina; Dicloxacilline; Dicloxacillinum; Dicloxacycline; Dycill; Dynapen; Maclicine; Methyldichlorophenylisoxazolylpenicillin; Pathocil; Diclossacillina [DCIT]; Dicloxacillin sodium; BRL 1702; Diclocil (TN); Dicloxacilina [INN-Spanish]; Dicloxacilline [INN-French]; Dicloxacillinum [INN-Latin]; R-13423; Dicloxacillin (USAN/INN); Dicloxacillin [USAN:INN:BAN]; Dicloxacillin, Monosodium Salt, Mono-Hydrate; (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; (2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolylpenicillin; 6-(3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 6-(3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid; 6beta-{[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carboxamido}-2,2-dimethylpenam-3alpha-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]
Staphylococcal pneumonia	N.A.	Approved	[2]
Staphylococcus aureus infection	N.A.	Approved	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

470.3

Logarithm of the Partition Coefficient (xlogp)

2.9

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

7

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 67.5% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2 mL/min/kg [5]
Elimination: 60% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.7 hours [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 35.50665 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.033% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.11 L/kg [5]

Chemical Identifiers

Formula: C19H17Cl2N3O5S
IUPAC Name: (2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES: CC1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI: 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
InChIKey: YFAGHNZHGGCZAX-JKIFEVAISA-N

Cross-matching ID

PubChem CID: 18381
ChEBI ID: CHEBI:4511
CAS Number: 3116-76-5
DrugBank ID: DB00485
TTD ID: D0R2KJ
VARIDT ID: DR00455
ACDINA ID: D00193

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Binder	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 2 (SLC15A2)	DT8QKNP	S15A2_HUMAN	Substrate	[8]
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[8]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[9]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[10]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[11]
Intercellular adhesion molecule 1 (ICAM1)	OTTOIX77	ICAM1_HUMAN	Gene/Protein Processing	[12]
Nuclear receptor subfamily 1 group I member 2 (NR1I2)	OTC5U0N5	NR1I2_HUMAN	Gene/Protein Processing	[13]
Protein S100-A8 (S100A8)	OTVMOB3F	S10A8_HUMAN	Gene/Protein Processing	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Dicloxacillin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Dicloxacillin due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[15]
Probenecid	DMMFWOJ	Minor	Decreased elimination of Dicloxacillin caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[16]
Methotrexate	DM2TEOL	Major	Decreased elimination of Dicloxacillin caused by Methotrexate mediated competitive inhibition of renal tubular secretion.	Leukaemia [2A60-2B33]	[17]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Dicloxacillin due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[15]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Carboxymethylcellulose sodium	E00621	Not Available	Adsorbent; Binding agent; Disintegrant; Emulsifying agent; Suspending agent; Viscosity-controlling agent
Ferrosoferric oxide	E00231	14789	Colorant
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sorbitan monolaurate	E00508	11046239	Dispersing agent; Emulsifying agent; Solubilizing agent; Surfactant; Suspending agent; Vaccine adjuvant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 14 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Dicloxacillin 250 mg capsule	250 mg	Oral Capsule	Oral
Dicloxacillin 500 mg capsule	500 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 062286.
2	Dicloxacillin FDA Label
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Mechanisms of resistance to beta-lactam antibiotics in Staphylococcus aureus. Scand J Infect Dis Suppl. 1984;42:64-71.
8	Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60.
9	Can the enhanced renal clearance of antibiotics in cystic fibrosis patients be explained by P-glycoprotein transport? Pharm Res. 2002 Apr;19(4):457-62.
10	Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
11	A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97.
12	Dicloxacillin and erythromycin at high concentrations increase ICAM-1 expression by endothelial cells: a possible factor in the pathogenesis of infusion phlebitis. J Antimicrob Chemother. 2004 Feb;53(2):174-9. doi: 10.1093/jac/dkh056. Epub 2004 Jan 16.
13	Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
14	Prediction of drug-induced liver injury using keratinocytes. J Appl Toxicol. 2017 Jul;37(7):863-872. doi: 10.1002/jat.3435. Epub 2017 Jan 31.
15	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
16	Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]
17	Kwon OC, Lee JS, Kim YG, Lee CK, Yoo B, Hong S. Safety of the concomitant use of methotrexate and a prophylactic dose of trimethoprim-sulfamethoxazole.?Clin Rheumatol. 2018;37(12):3215-3220. [PMID: 29383453]