ID: ALA1628

Max Phase: Preclinical

Molecular Formula: C28H42Cl2N10O7

Molecular Weight: 505.46

Molecule Type: Small molecule

Representations

Synonyms Trade Names(16): Bioscrub | Brian Care | Chg Scrub | Chlorhexidine Gluconate | Cida-Stat | Dyna-Hex | E-Z Scrub | Exidine | Hibiclens | Microderm | Peridex | Periochip | Periogard | Pharmaseal Scrub Care | Prevacare R | Steri-Stat

Canonical SMILES:  N=C(NCCCCCCNC(=N)NC(=N)Nc1ccc(Cl)cc1)NC(=N)Nc1ccc(Cl)cc1.O=C(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO

Standard InChI:  InChI=1S/C22H30Cl2N10.C6H12O7/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18;7-1-2(8)3(9)4(10)5(11)6(12)13/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2-5,7-11H,1H2,(H,12,13)/t;2-,3-,4+,5-/m.1/s1

Standard InChI Key:  KUXUALPOSMRJSW-IFWQJVLJSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 505.46

Molecular Weight (Monoisotopic): 504.2032

AlogP: 4.18

#Rotatable Bonds: 9

Polar Surface Area: 167.58

Molecular Species: BASE

HBA: 4

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 10.45

CX LogP: 4.51

CX LogD: -1.30

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: -0.36

References

1. Maeda S, Kita T, Meguro K..  (2009)  Synthesis of novel 4,6-di(substituted)amino-1,2-dihydro-1,3,5-triazine derivatives as topical antiseptic agents.,  52  (3): [PMID:19117423] [10.1021/jm8014712]

2. Maseda H, Hashida Y, Konaka R, Shirai A, Kourai H..  (2009)  Mutational upregulation of a resistance-nodulation-cell division-type multidrug efflux pump, SdeAB, upon exposure to a biocide, cetylpyridinium chloride, and antibiotic resistance in Serratia marcescens.,  53  (12): [PMID:19752278] [10.1128/aac.00631-09]

3. Karpanen TJ, Worthington T, Conway BR, Hilton AC, Elliott TS, Lambert PA..  (2008)  Penetration of chlorhexidine into human skin.,  52  (10): [PMID:18676882] [10.1128/aac.00637-08]

4. Nakaminami H, Noguchi N, Sasatsu M..  (2010)  Fluoroquinolone efflux by the plasmid-mediated multidrug efflux pump QacB variant QacBIII in Staphylococcus aureus.,  54  (10): [PMID:20660673] [10.1128/aac.01065-09]

5. Coburn RA, Baker PJ, Evans RT, Genco RJ, Fischman SL..  (1978)  In vitro antiplaque properties of a series of alkyl bis(biguanides).,  21  (8): [PMID:691009] [10.1021/jm00206a024]

6. Patel, Anjali, Dey, Subhasis, Shokeen, Kamal, Karpinski, Tomasz M., Sivaprakasam, Senthilkumar, Kumar, Sachin, Manna, Debasis.  (2021)  Sulfonium-based liposome-encapsulated antibiotics deliver a synergistic antibacterial activity,  12  (6.0): [PMID:34223166] [10.1039/d1md00091h]

Source

Source(1):

• Scientific Literature