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Penam information


Penam
Names
IUPAC name
(5R)-4-thia-1-azabicyclo[3.2.0]heptan-7-one
Other names
1-Aza-7-oxo-4-thiabicyclo[3.2.0]heptane
Identifiers
CAS Number
  • 53908-04-6 ☒N[ChemSpider]
3D model (JSmol)
  • Interactive image
Beilstein Reference
4374479
ChEBI
  • CHEBI:35991 checkY
ChemSpider
  • 7827765
PubChem CID
  • 9548842
InChI
  • InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
    Key: WSHJJCPTKWSMRR-RXMQYKEDSA-N
  • InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
    Key: WSHJJCPTKWSMRR-RXMQYKEDSA-N
SMILES
  • C1CSC2N1C(=O)C2
Properties
Chemical formula
C5H7NOS
Molar mass 129.18 g·mol−1
Related compounds
Related compounds
clavam
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Benzylpenicillin, an example of a penam

Penams are the primary skeleton structures that define the penicillin subclass of the broader β-lactam family of antibiotics and related compounds. They are bicyclic ring systems containing a β-lactam moiety fused with a five-member thiazolidine ring. [1] Due to ring strain and limitations on amide resonance, the structure is unstable and highly susceptible to catalytic cleavage at the amide bond.[2] Benzylpenicillin (penicillin G) is the natural product parent that contains the penam structure.

  1. ^ Novak, Igor; Chua, Pei Juan (2006-09-01). "Computational Study of Pharmacophores: β-Lactams". The Journal of Physical Chemistry A. 110 (35): 10521–10524. Bibcode:2006JPCA..11010521N. doi:10.1021/jp063162b. ISSN 1089-5639. PMID 16942059.
  2. ^ Patrick, Graham (2017-03-23), "5. Pharmaceuticals and medicinal chemistry", Organic Chemistry: A Very Short Introduction, Oxford University Press, pp. 71–89, doi:10.1093/actrade/9780198759775.003.0005, ISBN 978-0-19-875977-5

and 18 Related for: Penam information

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Penam

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Penams are the primary skeleton structures that define the penicillin subclass of the broader β-lactam family of antibiotics and related compounds. They...

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Penicillin

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condition is known as livedoid dermatitis or Nicolau syndrome. The term "penam" is used to describe the common core skeleton of a member of the penicillins...

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Side effects of penicillin

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Penicillins (Penams) Carbapenems / Penems Carbapenems (Ertapenem Antipseudomonal (Doripenem Imipenem Meropenem) Biapenem‡ Panipenem) Penems (Faropenem...

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Sulbactam

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2004). "Beta-lactams in the new millennium. Part-II: cephems, oxacephems, penams and sulbactam". Mini Reviews in Medicinal Chemistry. 4 (1): 93–109. doi:10...

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Benzathine benzylpenicillin

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Penicillins (Penams) Carbapenems / Penems Carbapenems (Ertapenem Antipseudomonal (Doripenem Imipenem Meropenem) Biapenem‡ Panipenem) Penems (Faropenem...

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Bactericide

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cell wall synthesis: the beta-lactam antibiotics (penicillin derivatives (penams), cephalosporins (cephems), monobactams, and carbapenems) and vancomycin...

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Morlachs

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totidem tempore quando reuertuntur ad montem; et si plus stant, incidunt ad penam quingentarum librarum. Mužić 2010, p. 13: Cum rectores Jadre scripserint...

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Carbapenem

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terms of structure, the carbapenems are very similar to the penicillins (penams), but the sulfur atom in position 1 of the structure has been replaced with...

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Phonological history of French

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lingua > langue /lɑ̃g/ "tongue" [citation needed] open /ein/ /ẽn/ /ɛn/ pēnam > peine /pɛn/ "sorrow, trouble" late closed /ẽ/ /ɛ̃/ [æ̃] plēnvm > plein...

Word Count : 4992

Avibactam

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Penicillins (Penams) Carbapenems / Penems Carbapenems (Ertapenem Antipseudomonal (Doripenem Imipenem Meropenem) Biapenem‡ Panipenem) Penems (Faropenem...

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C5H7NOS

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(molar mass: 129.18 g/mol, exact mass: 129.0248 u) may refer to: Goitrin Penam This set index page lists chemical structure articles associated with the...

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Cloisters Cross

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texts. One reads Cham ridet dum nuda pudibunda parentis; Iudei risere Dei penam mor[ientis], or "Cham laughed when he saw his parent's shameful nudity;...

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Lodi Gyari

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children, Tenzing Dechen, Tenzing Choyang, Norbu Wangmo, Tashi Chodon, Tulku Penam and Tenzing Tsering, five grandchildren, his mother, and four brothers and...

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Epicillin

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Penicillins (Penams) Carbapenems / Penems Carbapenems (Ertapenem Antipseudomonal (Doripenem Imipenem Meropenem) Biapenem‡ Panipenem) Penems (Faropenem...

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Cefozopran

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Penicillins (Penams) Carbapenems / Penems Carbapenems (Ertapenem Antipseudomonal (Doripenem Imipenem Meropenem) Biapenem‡ Panipenem) Penems (Faropenem...

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Carumonam

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Penicillins (Penams) Carbapenems / Penems Carbapenems (Ertapenem Antipseudomonal (Doripenem Imipenem Meropenem) Biapenem‡ Panipenem) Penems (Faropenem...

Word Count : 82

Vlachs in the history of Croatia

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totidem tempore quando reuertuntur ad montem; et si plus stant, incidunt ad penam quingentarum librarum. Botica 2005, p. 39. Mužić 2010, p. 230. Mužić 2009...

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Clavam

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antibiotic and 5S clavams may have anti-fungal properties. They are similar to penams, but with an oxygen substituted for the sulfur. Thus, they are also known...

Word Count : 714

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