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SID49732002

ID: ALA1201057

Cas Number: 81129-83-1

PubChem CID: 23663403

Product Number: C275313, Order Now?

Max Phase: Approved

First Approval: 1985

Molecular Formula: C16H25N2NaO5S

Molecular Weight: 358.46

Molecule Type: Small molecule

In stock!

Associated Items:

Names and Identifiers

Synonyms: Cilastatin sodium | MK-791 | Cilastatin sodium|81129-83-1|Cilastatin sodium salt|CILASTATIN Na|MLS001401364|DTXSID2046915|MK-791|Sodium (Z)-7-(((R)-2-amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropane-1-carboxamido)hept-2-enoate|sodium;(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoate|Sodium;(Z)-7-[(2S)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoate|DTXCID0026915|CHEBI:59511|CAS-81129-8Show More

Canonical SMILES:  CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C16H26N2O5S.Na/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21;/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23);/q;+1/p-1/b12-6-;/t10-,11+;/m1./s1

Standard InChI Key:  QXPBTTUOVWMPJN-QBNHLFMHSA-M

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
    5.9667   -6.9375    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    4.5208   -5.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1583   -4.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -5.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -6.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -8.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1458   -6.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1458   -6.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -7.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -9.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -8.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -7.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375   -4.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -6.8625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458   -6.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  2  5  1  6
  6  5  1  0
  7  6  1  0
  8  7  1  0
  9 10  1  0
 10 21  1  1
 11  5  2  0
 12  8  1  0
 13  8  2  0
 14  9  2  0
 15  7  2  0
 16 10  1  0
 17  9  1  0
 18  3  1  0
 19  3  1  0
 20 23  1  0
 21 20  1  0
 22 15  1  0
 23 25  1  0
 24 22  1  0
 25 24  1  0
  4  3  1  0
M  CHG  2   1   1  12  -1
M  END

Associated Targets(Human)

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAN Tchem GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 (21853 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERG Tbio Transcriptional regulator ERG (5589 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
Plasmodium falciparum (966862 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
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cryptococcus neoformans (21258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 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: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

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Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 358.46Molecular Weight (Monoisotopic): 358.1562AlogP: 1.43#Rotatable Bonds: 11
Polar Surface Area: 129.72Molecular Species: ZWITTERIONHBA: 5HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 2.53CX Basic pKa: 9.14CX LogP: -1.27CX LogD: -4.19
Aromatic Rings: Heavy Atoms: 24QED Weighted: 0.32Np Likeness Score: 0.74

References

1. PubChem BioAssay data set, 
2. Unpublished dataset, 
3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
4. PubChem BioAssay data set, 
5. Unpublished dataset, 
6. 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]
7. 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]
8. 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]
9. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]