Details of the Drug

General Information of Drug (ID: DMHSJB4)

Drug Name
Cyclacillin
Synonyms
Aminocyclohexylpenicillin; Bastcillin; Calthor; Ciclacilina; Ciclacillin; Ciclacilline; Ciclacillinum; Ciclacillum; Citosarin; Cyclapen; Noblicil; Orfilina; Peamezin; Syngacillin; Ultracillin; Vastcillin; Vipicil; Wyvital; Aminocyclohexyl penicillin; Cyclacillin [USAN]; AC 98; WY 4508; WY4508; C-12104; Ciclacilina [INN-Spanish]; Ciclacilline [INN-French]; Ciclacillinum [INN-Latin]; Cyclacillin (USAN); Cyclapen (TN); Cyclapen-W; Vastcillin (TN); Wy-4508; Ciclacillin (JP15/INN); Cyclapen-W (TN); (1-Aminocyclohexyl)penicillin; (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-(8CI); 6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(1-Aminocyclohexanecarboxamido)penicillanic acid; 6-(1-Aminocyclohexylcarboxamido)penicillanic acid; 6beta-(1-aminocyclohexanecarboxamido)-2,2-dimethylpenam-3alpha-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Bronchitis CA20 Approved [2]
Urinary tract infection GC08 Approved [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 341.4
Logarithm of the Partition Coefficient (xlogp) 1.3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption
The drug is moderately absorbed []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 97.53033 micromolar/kg/day [3]
Chemical Identifiers
Formula
C15H23N3O4S
IUPAC Name
(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
InChI
InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
InChIKey
HGBLNBBNRORJKI-WCABBAIRSA-N
Cross-matching ID
PubChem CID
19003
ChEBI ID
CHEBI:31444
CAS Number
3485-14-1
DrugBank ID
DB01000
TTD ID
D00HWO
VARIDT ID
DR00480
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 2 (SLC15A2) DT8QKNP S15A2_HUMAN Substrate [5]
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4817).
2 Cyclacillin FDA Label
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
5 Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60.