Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5199)
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 Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 341.4 Topological Polar Surface Area 138
Heavy Atom Count 23 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
19003
ChEBI ID
CHEBI:31444
CAS Number
3485-14-1
TTD Drug ID
D00HWO
Formula
C15H23N3O4S
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
6-APA DM001190
11082
Hydrolysis - Hydrolysis 1 [2]
ACHC DM015516
7005079
Hydrolysis - Hydrolysis 1 [2]
Cyclacillin penicilloic acid DM017095 N. A. Unclear - Opening of the _x0002_lactam ring 1 [2]
ACHC DM015516
7005079
Hydrolysis - Hydrolysis 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008095 Cyclacillin Cyclacillin penicilloic acid Unclear - Opening of the _x0002_lactam ring Unclear [2]
MR008097 Cyclacillin ACHC Hydrolysis - Hydrolysis Unclear [2]
MR008098 Cyclacillin 6-APA Hydrolysis - Hydrolysis Unclear [2]
MR008096 Cyclacillin penicilloic acid ACHC Hydrolysis - Hydrolysis Unclear [2]
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 Sex- and species-related nephropathy of 6-(1-aminocyclohexanecarboxamido)penicillanic acid (cyclacillin) and its relationship to the metabolic disposition of the drug

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