meticillin
Approved
Jun 1, 1960
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. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 2 marketing orgs
Timeline
1960s
- Jun 1, 1960
Earliest FDA Approval
1970s
- Apr 1, 1971
Apothecon — Marketing Organization
Indications
Approved for
Mechanism of action
- Penicillin-binding proteinINHIBITOR
Penicillin-binding protein inhibitor
- Penicillin-binding protein 4 (pbp4) ↗
- Cell division protein FtsI [Peptidoglycan synthetase] / Transpeptidase, Penicillin binding protein transpeptidase domain, Penicillin-binding protein 3 (pbpF) ↗
- MecA PBP2' (penicillin binding protein 2') (Q53707) ↗
- Penicillin-binding protein 2 (Q53729) ↗
- Cell division protein FtsI (Peptidoglycan synthetase) (pbpA) ↗
Approval history
- approvedJun 1, 1960
Chemistry & pharmacology
SMILES
COc1cccc(OC)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)[O-].O.[Na+]- Mol. weight
- 420.42 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL3181832 ↗
- WikipediaMethicillin ↗
- NCATSQ91FH1328A ↗
- ChEMBLCHEMBL575 ↗
- ChEMBLCHEMBL1164 ↗
Also known as
- (2,6-dimethoxyphenyl)penicillin
- (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-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 6-(2,6-dimethoxybenzamido)penicillanic acid
- 6-(2,6-dimethoxybenzamido)penicillanic acid
- 6beta-(2,6-dimethoxybenzamido)penicillanic acid
- 6beta-(2,6-dimethoxybenzamido)penicillanic acid
- brl-1241
- brl-1241
- celbenin
- celbenin
- metacillin
- methicillin
- methicillin
- methicillin
- methicillin
- methicillin
- methicillin
- methicillin sodium
- methicillin sodium
- methicillin sodium
- methicillin sodium
- methicillinum
- methicillinum
- methycillin
- methycillin
- methycillin
- meticilina
- meticilina
- meticillin
- meticillin
- meticillin
- meticillin
- meticillin
- meticillin
- meticilline
- meticilline
- meticillin sodium
- meticillin sodium
- meticillin sodium
- meticillin sodium
- meticillin sodium
- meticillin sodium
- meticillinum
- meticillinum
- sq-16123
- sq-16123
- staphcillin
- staphcillin
- staphcillin
- staphcillin
- x-1497
- x-1497