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SID56463238

ID: ALA1200589

Cas Number: 66309-69-1

PubChem CID: 20848883

Max Phase: Approved

First Approval: 1988

Molecular Formula: C18H24ClN9O4S3

Molecular Weight: 525.64

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Synonyms: Cefotiam dihydrochloride | Cefotiam hcl | ABBOTT-48999 | CGP-14221/E | NSC-758164 | SCE 963 | SCE-963 | CEFOTIAM HYDROCHLORIDE|66309-69-1|SCE 963|DTXCID9025538|(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride|sodium;(6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|CAS-66309-6Show More

Trade Names(2): Ceradon | Pansporin

Canonical SMILES:  CN(C)CCn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1.Cl

Standard InChI:  InChI=1S/C18H23N9O4S3.ClH/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10;/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31);1H/t12-,15-;/m1./s1

Standard InChI Key:  SVSFIELZISOJDT-XRZFDKQNSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3667   -7.6875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -6.4583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -6.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -6.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -6.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -7.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5583   -7.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -6.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -5.4000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7958   -6.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -5.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -5.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167   -6.4208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -6.4708    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -5.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -5.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -6.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -6.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -6.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -7.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -6.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -5.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8208   -5.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4333   -5.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -7.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4333   -6.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0458   -5.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -5.0417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  4  1  0
  6  7  1  0
  7 21  1  0
  8  2  1  0
  9  7  2  0
 10  9  1  0
 11  6  1  0
 12  4  1  0
 13  8  2  0
 14 17  1  0
 15 14  2  0
  5 16  1  1
 17 22  1  0
 18  8  1  0
 19 25  1  0
 20 16  1  0
 21 27  1  0
 22 20  1  0
 23  6  1  0
 24 12  1  0
 25 17  2  0
 26  3  2  0
 27 13  1  0
 28 18  2  0
 29 20  2  0
 30 15  1  0
 31 23  1  0
 32 31  1  0
 33 18  1  0
 34 32  1  0
 35 32  1  0
  4 36  1  6
  3  5  1  0
 24 13  1  0
 11 10  2  0
 19 15  1  0
M  END

Associated Targets(Human)

L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KPNB1 Tbio Importin subunit beta-1/Snurportin-1 (25097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLI Tchem DNA polymerase iota (116820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FEN1 Tchem Flap endonuclease 1 (12055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLH Tchem DNA polymerase eta (21678 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

TGR Thioredoxin glutathione reductase (28579 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ampC Beta-lactamase AmpC (62480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pfk 6-phospho-1-fructokinase (7870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: Yes
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences
Bacterial penicillin-binding protein inhibitorINHIBITORALA2354204Bacterial penicillin-binding proteinPROTEIN FAMILYBacteria

PubMed: [1]


Calculated Properties

Molecular Weight: 525.64Molecular Weight (Monoisotopic): 525.1035AlogP: -0.65#Rotatable Bonds: 10
Polar Surface Area: 172.46Molecular Species: ACIDHBA: 13HBD: 3
#RO5 Violations: 2HBA (Lipinski): 13HBD (Lipinski): 4#RO5 Violations (Lipinski): 2
CX Acidic pKa: 2.84CX Basic pKa: 8.34CX LogP: -3.09CX LogD: -3.11
Aromatic Rings: 2Heavy Atoms: 34QED Weighted: 0.26Np Likeness Score: -1.77

References

1. PubChem BioAssay data set, 
2. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]
3. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]
4. Unpublished dataset, 
5. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]
6. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
7. PubChem BioAssay data set, 
8. PubChem BioAssay data set, 
9. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]
10. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]
11. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
12. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
13. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
14. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]