Structure via PubChem · Public domain (PubChem)
amdinocillin
Sign in to saveAlso known as Ro-109070, Coactin, Penicillin HX, mecillinam
Mecillinam (INN) or amdinocillin (USAN) is an extended-spectrum penicillin antibiotic of the amidinopenicillin class that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has also been used to treat typhoid and paratyphoid fever. Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam.
Chemical data
- Formula
- C15H23N3O3S
- Molecular weight
- 325.4 g/mol
- IUPAC name
- (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C
- InChIKey
- BWWVAEOLVKTZFQ-NTZNESFSSA-N
- XLogP
- 2.1
- Polar surface area
- 98.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1984
- Admin. routes
- parenteral
- Indications
- bacterial disease
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 325.14601259599993
- Has use
- medication
Show 7 more facts
- chemical formula
- C₁₅H₂₃N₃O₃S
- isomeric SMILES
- CC1(C)S[C@@H]2[C@H](\N=C\N3CCCCCC3)C(=O)N2[C@H]1C(=O)O
- NCI Thesaurus ID
- C65229
- defined daily dose
- 1.2
- subject has role
- bactericide
- Commons category
- Mecillinam
- canonical SMILES
- CC1(C)SC2C(N=CN3CCCCCC3)C(=O)N2C1C(=O)O
Sources (3)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Medical uses
- Adverse effects
- History
- References
Mecillinam (INN) or amdinocillin (USAN) is an extended-spectrum penicillin antibiotic of the amidinopenicillin class that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has also been used to treat typhoid and paratyphoid fever. Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam.
==Medical uses== Mecillinam is used in the treatment of infections due to susceptible gram-negative bacteria, especially urinary tract infections which are most commonly caused by Escherichia coli. Mecillinam is active against most pathogenic Gram-negative bacteria, except Pseudomonas aeruginosa and some species of Proteus. Several studies have also found it to be as effective as other antibiotics for treating Staphylococcus saprophyticus infection, though it is Gram-positive, possibly because mecillinam reaches very high concentrations in urine.
Excerpted from Wikipedia’s “amdinocillin” article, available under the CC BY-SA 4.0 licence.