Details of the Drug

General Information of Drug (ID: DMIKHN0)

Drug Name

Meticillin

Synonyms

Dimocillin; MII; Metacillin; Methicillin; Methicillinum; Methycillin; Meticilina; Meticillina; Meticilline; Meticillinum; Staphcillin; Methicillin [BAN]; Meticillin [INN]; Meticillina [DCIT]; BRL 1241; Methicillin Monohydrate, Monosodium Salt; Meticilina [INN-Spanish]; Meticilline [INN-French]; Meticillinum [INN-Latin]; Penicillin, Dimethoxyphenyl; (2,6-Dimethoxyphenyl)penicillin; (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(2,6-dimethoxyphenyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(2,3-Dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 6-(2,6-Dimethoxybenzamido)penicillanic acid; 6beta-(2,6-dimethoxybenzamido)-2,2-dimethylpenam-3alpha-carboxylic acid; 6beta-(2,6-dimethoxybenzamido)penicillanic acid

Indication

Disease Entry	ICD 11	Status	REF
Bacteremia	1A73	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Staphylococcal pneumonia	N.A.	Approved	[3]
Neurological disorder	6B60	Investigative	[4]
Sinusitis	CA0A.Z	Investigative	[5]
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Therapeutic Class

Antibiotics

Affected Organisms

Enteric bacteria and other eubacteriaStaphylococcus aureusGram-positive BacteriaStaphylococcus epidermidisStreptococcus pyogenesStreptococcus pneumoniae

ATC Code

J01CF03: Meticillin

J01CF: Beta-lactamase resistant penicillins

J01C: BETA-LACTAM ANTIBACTERIALS, PENICILLINS

J01: ANTIBACTERIALS FOR SYSTEMIC USE

J: ANTIINFECTIVES FOR SYSTEMIC USE

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

380.4

Logarithm of the Partition Coefficient (xlogp)

1.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is not absorbed after oral administration []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [6]
Clearance: The drug present in the plasma can be removed from the body at the rate of 6.6 mL/min/kg [7]
Elimination: 88% of drug is excreted from urine in the unchanged form [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 25 - 60 minutes [7]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 16.43 micromolar/kg/day [8]
Unbound Fraction: The unbound fraction of drug in plasma is 0.43% [7]
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 0.32 L/kg [7]
Water Solubility: The ability of drug to dissolve in water is measured as 300 mg/mL [6]

Chemical Identifiers

Formula: C17H20N2O6S
IUPAC Name: (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
InChI: InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
InChIKey: RJQXTJLFIWVMTO-TYNCELHUSA-N

Cross-matching ID

PubChem CID: 6087
ChEBI ID: CHEBI:6827
CAS Number: 61-32-5
UNII: Q91FH1328A
DrugBank ID: DB01603
TTD ID: D06TQZ

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	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Post-COVID-19 Infection With Meticillin-Sensitive Staphylococcus aureus (MSSA) Bacteremia, Discitis/Osteomyelitis, and Diffuse Abscesses: A Case Report. Cureus. 2022 Jun 10;14(6):e25824.
2	Drug information of Meticillin, 2008. eduDrugs.
3	[Staphylococcal pneumonia]. Probl Tuberk Bolezn Legk. 2004;(6):11-7.
4	Alpha-conotoxins. Int J Biochem Cell Biol. 2000 Oct;32(10):1017-28.
5	Diagnosis, management and treatment of orbital and periorbital cellulitis in children. Emerg Nurse. 2016 Apr;24(1):30-5; quiz 37.
6	BDDCS applied to over 900 drugs
7	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8	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
9	A link in transcription between the native pbpB and the acquired mecA gene in a strain of Staphylococcus aureus. Microbiology. 2006 Sep;152(Pt 9):2549-58.