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 Y

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

Tracking categories (test):

* SizeSet

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.

## Structure

Penams have inflexible structures. The structure is locked in a puckered (i.e. bent) shape due to the pyramidal geometry of the bridgehead nitrogen. The pyramidalization (χ = 54°) and twist of the C-N bond (τ = 18°) is caused by the strain from the lone pair's exclusion from planarity with the cyclic rings and electrostatic repulsion effects. As a result, the distorted C-N bond causes misalignment the orbitals of the carbonyl carbon and the nitrogen lone pair that allow for resonance overlap. The amide C-N bond length is 1.406 Å and displays greater single bond character than in noncyclic tertiary amides. The C-O bond length is 1.205 Å which is shorter than C-O bonds in noncyclic tertiary amides.[3]

Penams are strained associated with the four-member β-lactam ring, whose internal bond angles are 90º.[4][3] Consequently, penams are susceptible to acid- and base-catalyzed hydrolysis.[1][4]

## References

1. ↑ 1.0 1.1 Novak, Igor; Chua, Pei Juan (2006-09-01). "Computational Study of Pharmacophores: β-Lactams". The Journal of Physical Chemistry A 110 (35): 10521–10524. doi:10.1021/jp063162b. ISSN 1089-5639. PMID 16942059. Bibcode: 2006JPCA..11010521N.
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
3. ↑ 3.0 3.1 Glover, Stephen A.; Rosser, Adam A. (2012-06-14). "Reliable Determination of Amidicity in Acyclic Amides and Lactams". The Journal of Organic Chemistry 77 (13): 5492–5502. doi:10.1021/jo300347k. ISSN 0022-3263. PMID 22646836.
4. ↑ 4.0 4.1 Hu, Feng; Lalancette, Roger; Szostak, Michal (2016-03-08). "Structural Characterization of N-Alkylated Twisted Amides: Consequences for Amide Bond Resonance and N−C Cleavage". Angewandte Chemie International Edition 55 (16): 5062–5066. doi:10.1002/anie.201600919. ISSN 1433-7851. PMID 26953809.

* v
* t
* e

Antibiotics active on the cell wall and envelope (J01C-J01D)

Intracellular|

* Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
* DADAL/AR inhibitors (Cycloserine)
* bactoprenol inhibitors (Bacitracin)

Glycopeptide|

* Inhibit PG chain elongation: Vancomycin# (Oritavancin
* Telavancin)
* Teicoplanin (Dalbavancin)
* Ramoplanin§

β-lactams/
(inhibit PBP
cross-links)|

| Penicillins
(Penams)|

| Narrow
spectrum|

| β-lactamase sensitive
(1st generation)|

* Benzylpenicillin (G)#
* Benzathine benzylpenicillin#
* Procaine benzylpenicillin#
* Phenoxymethylpenicillin (V)#
* Propicillin‡
* Pheneticillin‡
* Azidocillin‡
* Clometocillin‡
* Penamecillin‡

|

β-lactamase resistant
(2nd generation)|

* Cloxacillin# (Dicloxacillin
* Flucloxacillin)
* Oxacillin
* Nafcillin
* Methicillin‡

Extended
spectrum|

| Aminopenicillins (3rd generation)|

* Amoxicillin#
* Ampicillin# (Pivampicillin
* Hetacillin‡
* Bacampicillin‡
* Metampicillin‡
* Talampicillin‡)
* Epicillin‡

|

Carboxypenicillins (4th generation)|

* Ticarcillin
* Carbenicillin‡ / Carindacillin‡
* Temocillin‡

Ureidopenicillins (4th generation)|

* Piperacillin
* Azlocillin‡
* Mezlocillin‡

Other|

* Mecillinam‡ (Pivmecillinam‡)
* Sulbenicillin‡

Penems|

* Faropenem‡
* Ritipenem§

Carbapenems|

* Ertapenem
* Antipseudomonal (Doripenem
* Imipenem
* Meropenem)
* Biapenem‡
* Panipenem‡

Cephalosporins
/ Cephamycins
(Cephems)|

| 1st generation|

* Cefazolin#
* Cefalexin #
* Cefadroxil
* Cefapirin
* Cefazedone‡
* Cefazaflur‡
* Cefradine‡
* Cefroxadine‡
* Ceftezole‡
* Cefaloglycin‡
* Cefacetrile‡
* Cefalonium‡
* Cefaloridine‡
* Cefalotin‡
* Cefatrizine‡

|

2nd generation|

* Cefaclor
* Cefotetan
* Cephamycin (Cefoxitin
* Cefprozil
* Cefuroxime
* Cefuroxime axetil
* Cefamandole‡
* Cefminox‡
* Cefonicid‡
* Ceforanide‡
* Cefbuperazone‡
* Cefuzonam‡
* Cefmetazole‡)
* Carbacephem‡ (Loracarbef‡)

3rd generation|

* Cefixime#
* Ceftriaxone#
* Cefotaxime#
* Antipseudomonal (Ceftazidime#
* Cefoperazone‡)
* Cefdinir
* Cefcapene
* Cefdaloxime
* Ceftizoxime
* Cefmenoxime
* Cefpiramide
* Cefpodoxime
* Ceftibuten
* Cefditoren
* Cefotiam‡
* Cefetamet‡
* Cefodizime‡
* Cefpimizole‡
* Cefsulodin‡
* Cefteram‡
* Ceftiolene‡
* Oxacephem (Flomoxef‡
* Latamoxef‡)

4th generation|

* Cefepime
* Cefozopran‡
* Cefpirome‡
* Cefquinome‡

5th generation|

* Ceftaroline fosamil
* Ceftolozane
* Ceftobiprole

Veterinary|

* Ceftiofur
* Cefquinome
* Cefovecin

Monobactams|

* Aztreonam#
* Tigemonam‡
* Carumonam‡
* Nocardicin A‡

β-lactamase inhibitors|

* Penam (Sulbactam
* Tazobactam)
* Clavam (Clavulanic acid]])
* Sulbactam
* non-β-lactam (Relebactam
* Avibactam
* Vaborbactam)

Combinations|

* Amoxicillin/clavulanic acid#
* Imipenem/cilastatin#
* Imipenem/cilastatin/relebactam
* Ampicillin/flucloxacillin
* Ampicillin/sulbactam (Sultamicillin)
* Ceftazidime/avibactam
* Piperacillin/tazobactam
* Ceftolozane/tazobactam
* Cefoperazone/sulbactam
* Meropenem/vaborbactam

Other|

* polymyxins/detergent
* Colistin
* Polymyxin B
* depolarizing
* Daptomycin
* Hydrolyze NAM-NAG
* lysozyme
* Tyrothricin
* Gramicidin
* Tyrocidine
* Isoniazid#
* Teixobactin

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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