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سیکلاسیلین

Structure via PubChem · Public domain (PubChem)

EntityQ5119441· pop 6· linked from 5 articles

سیکلاسیلین

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Also known as Cyclapen®, Vastcillin®, 6-(1-aminocyclohexanecarboxamido)penicillanic acid, 6-(1-aminocyclohexylcarboxamido)penicillanic acid, (1-aminocyclohexyl)penicillin, (2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, Bastcillin, Ciclacilline

Ciclacillin (INN) or cyclacillin (USAN), trade names Cyclapen, Cyclapen-W, Vastcillin, and others, is an aminopenicillin antibiotic. Its spectrum of activity is similar to that of ampicillin, although it is less susceptible to beta-lactamases than ampicillin and has much higher bioavailability. A large randomized, double-blind clinical trial published in 1978 also showed that ciclacillin is associated with significantly fewer and milder adverse effects than ampicillin; later studies seemed to confirm this improved tolerability, at least in children.

Chemical data

Formula
C15H23N3O4S
Molecular weight
341.4 g/mol
IUPAC name
(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-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)NC(=O)C3(CCCCC3)N)C(=O)O)C
InChIKey
HGBLNBBNRORJKI-WCABBAIRSA-N
XLogP
1.3
Polar surface area
138 Ų
H-bond donors
3
H-bond acceptors
6
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
1979
Admin. routes
oral

via ChEMBL · EBI

Wikidata facts

Mass
341.140927
Has use
medication
Show 6 more facts
chemical formula
C₁₅H₂₃N₃O₄S
medical condition treated
bacterial infectious disease
canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
isomeric SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
World Health Organisation international non-proprietary name
ciclacillin
subject has role
bactericide
Sources (4)

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