U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H20N2O6S
Molecular Weight 380.415
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(OC)C=CC=C3OC)C(O)=O

InChI

InChIKey=RJQXTJLFIWVMTO-TYNCELHUSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H20N2O6S
Molecular Weight 380.415
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Methicillin sodium anhydrous is a sodium salt of methicillin (methicillin). Methicillin is an antibiotic formerly used in the treatment of bacterial infections caused by organisms of the genus Staphylococcus. Methicillin is a semisynthetic derivative of penicillin. It was first produced in the late 1950s and was developed as a type of antibiotic called penicillinase-resistant penicillin—it contained a modification to the original penicillin structure that made it resistant to a bacterial enzyme called penicillinase (beta-lactamase). Compared to other penicillins that face antimicrobial resistance due to β-lactamase, it is less active, can be administered only parenterally, and has a higher frequency of interstitial nephritis, an otherwise-rare adverse effect of penicillins. However, the selection of meticillin depended on the outcome of susceptibility testing of the sampled infection, and since it is no longer produced, it is also not routinely tested for anymore.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
STAPHCILLIN

Cmax

ValueDoseCo-administeredAnalytePopulation
25 μg/mL
15 mg/kg single, intravenous
METHICILLIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
27.5 μg × h/mL
15 mg/kg single, intravenous
METHICILLIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.05 h
15 mg/kg single, intravenous
METHICILLIN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Adults, teenagers, and children weighing more than 40 kilograms (kg) (88 pounds)—1 gram injected into a muscle every four to six hours; or 1 gram injected into a vein every six hours. Children weighing up to 40 kg (88 pounds)—Dose is based on body weight and must be determined by your doctor. The usual dose is 25 milligrams (mg) per kg (11.4 mg per pound) of body weight, injected into a vein or muscle every six hours.
Route of Administration: Intramuscular
In Vitro Use Guide
Determination of Meticillin susceptibility was done by plating diluted overnight cultures of strain COL on petri dishes containing tryptic soy agar (TSA; Difco) and serial (twofold) dilutions of the Meticillin. Colonies were counted after 48 h of incubation at 37 and 42°C. The high-level methicillin resistance at 37°C (MIC = 800 mkg/ml) was reduced to 12 mkg/ml at 42°C
Substance Class Chemical
Record UNII
Q91FH1328A
Record Status Validated (UNII)
Record Version