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Showing drug card for Cyclacillin (DB01000)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:03
Primary Accession Number DB01000
Secondary Accession Number
  • APRD00892
Name Cyclacillin
Drug Type
  • Approved
  • Small Molecule
Description A cyclohexylamido analog of penicillanic acid. [PubChem]
Synonyms
  1. Aminocyclohexylpenicillin
  2. Ciclacilina [INN-Spanish]
  3. Ciclacillin
  4. Ciclacilline [INN-French]
  5. Ciclacillinum [INN-Latin]
  6. Ciclacillum
Brand Names
  1. Bastcillin
  2. Calthor
  3. Citosarin
  4. Cyclapen
  5. Cyclapen-W
  6. Orfilina
  7. Syngacillin
  8. Ultracillin
  9. Vastcillin
  10. Vipicil
  11. Wyvital
Brand Mixtures Not Available
Chemical 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
Chemical Formula C15H23N3O4S
Chemical Structure Structure
CAS Registry Number 3485-14-1
InChI Identifier InChI=1/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/f/h17,20H
InChI Key HGBLNBBNRORJKI-LNONHFHSDY
KEGG Drug D01334 Link Image
KEGG Compound C12766 Link Image
PubChem Compound 19003 Link Image
PubChem Substance 583155 Link Image
ChEBI ID Not Available
PharmGKB ID PA449155 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 341.4260
Monoisotopic Molecular Weight 341.1409
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.90e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.4 Source: PhysProp
Predicted LogP 0.56 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.26 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(O)=O
Canonical SMILES CC1(C)SC2C(NC(=O)C3(N)CCCCC3)C(=O)N2C1C(O)=O
Drug Category
  • Anti-Bacterial Agents
  • Penicillins
ATC Codes Not Available
AHFS Codes Not Available
Indication For the treatment of bacterial infections caused by susceptible organisms.
Pharmacology Cyclacillin, a penicillin, is a cyclohexylamido analog of penicillanic acid. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. Cyclacillin has been replaced by newer penicillin treatments.
Mechanism of Action The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.
Absorption Moderately absorbed.
Toxicity Symptoms of overdose include severe diarrhea, nausea and vomiting.
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References Not Available
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Penicillin-binding proteins 1A/1B
  2. Oligopeptide transporter, small intestine isoform
Drug Target 1 [top]
Target 1 ID 633
Target 1 Name Penicillin-binding proteins 1A/1B
Target 1 Synonyms Not Available
Target 1 Gene Name pbpA
Target 1 Protein Sequence >Penicillin-binding proteins 1A/1B 
MTERKREHKDRKQNKNSPKNQSKVTKFLKWFFIGILLLGITAVTVVGIYVLSIIRSSPEL
DVQAIQSLNQPSILYDDQGNFMDNVITREQRYVVKSEEIPDNLKKAFVAIEDERFYEHKG
IDIKRIFGVIASNIKGKLSGSNTVQGASTITQQLIKNAVLTNEVSYERKIKEMYLALELE
KHLSKDEILTTYLNTIPMGGYQYGVSAAAQRFFSKNVSDLNLVECAYLGGLTQAPTSYDG
LSEANKENPSRYLNRTKSVLFKMHELGYISSEQYNDAINEIDTNGIKFTPNNKLSKTNFE
WFTRPAITQVKQDLMDKYKYTQEEVDKLIANGGLKIYTSMDRNLQNNVQKVLDDPNNYKA
ITNNPNEKNEDGVYKLQASATIIDYKTGHVKALVGGRGEQPAMSHNRAYYDLKSIGSATK
PLTVYGPAIDLGLGGAGSVVNDSPLSNKELSSTGYKDQPKNEYNSYRGPLTFREAIKISS
NLAAIKVANEVGVSNSIAYGEKLGLVYGPHSRGISTTALGQFQNDPNNPDGGNTYTLASA
FGVFGNNGVKTNAKLYTKVLDSHGNVILDTSTPEETKIFSPQASYIVYDMLKDQVESGSA
KSAKFGNIPVAGKTGTTTGDKDYLFAGLTPYYSAAIWIGYDKPREMRTSSGTVTSPIFGK
IMGLAHKDLQYKEVDNLVE
Target 1 Number of Residues 690
Target 1 Molecular Weight 75178
Target 1 Theoretical pI 9.09
Target 1 GO Classification
Function
binding
drug binding
penicillin binding
transferase activity
transferase activity, transferring glycosyl groups
transferase activity, transferring pentosyl groups
hydrolase activity
peptidase activity
catalytic activity
Process
cellular physiological process
cell organization and biogenesis
external encapsulating structure organization and biogenesis
cell wall organization and biogenesis
cell wall organization and biogenesis (sensu Bacteria)
cell wall biosynthesis (sensu Bacteria)
response to stimulus
response to abiotic stimulus
response to chemical stimulus
response to drug
response to antibiotic
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
cellular carbohydrate metabolism
peptidoglycan metabolism
peptidoglycan biosynthesis
Component
cell
external encapsulating structure
cell wall
cell wall (sensu Bacteria)
Target 1 General Function Cell wall/membrane/envelope biogenesis
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-52
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 18145626 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q8XJ01 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q8XJ01_CLOPE Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >2040 bp 
ATGACTGAAAGAAAAAGAGAGCATAAAGATAGAAAGCAGAATAAAAATTCACCTAAAAAT
CAATCGAAAGTAACAAAATTTTTGAAATGGTTCTTTATAGGGATTCTGCTTCTAGGGATA
ACTGCCGTAACAGTAGTTGGAATTTACGTTCTTTCTATTATACGTTCATCTCCAGAGTTA
GATGTTCAGGCAATTCAATCTCTAAATCAGCCATCCATTCTTTACGATGATCAGGGAAAC
TTTATGGATAATGTTATAACTCGTGAACAACGTTATGTAGTTAAATCTGAAGAGATACCT
GATAACTTAAAAAAGGCTTTTGTAGCTATTGAAGACGAAAGATTTTATGAGCATAAAGGA
ATAGACATTAAAAGAATTTTTGGGGTAATAGCTTCTAATATTAAAGGTAAACTTTCAGGA
AGTAATACAGTTCAAGGGGCTTCAACCATAACTCAGCAACTTATAAAAAATGCCGTACTT
ACTAATGAAGTTAGTTATGAAAGAAAAATTAAAGAAATGTACTTAGCTTTGGAATTAGAA
AAGCACCTTTCAAAAGATGAAATCCTTACTACGTATTTAAATACAATTCCTATGGGTGGA
TACCAATATGGGGTTAGCGCAGCTGCTCAAAGATTTTTTAGTAAGAATGTTTCAGATTTG
AATTTAGTTGAGTGCGCTTATTTAGGAGGACTTACTCAAGCACCAACTTCTTATGATGGT
CTTTCAGAAGCAAATAAAGAAAATCCAAGTAGATATTTAAATAGAACTAAATCTGTACTA
TTTAAAATGCATGAACTTGGATATATTTCAAGTGAACAATATAATGACGCAATAAATGAA
ATTGACACAAATGGTATAAAATTCACACCAAATAATAAATTAAGTAAAACTAACTTTGAG
TGGTTCACAAGACCAGCTATAACTCAAGTTAAACAAGACTTAATGGATAAATATAAATAT
ACACAAGAGGAAGTTGACAAACTTATAGCTAATGGTGGATTAAAAATCTATACTTCAATG
GATAGAAATCTTCAAAATAATGTTCAAAAAGTTTTAGATGATCCAAATAACTATAAAGCT
ATAACTAATAATCCTAATGAAAAAAATGAAGATGGTGTTTATAAATTACAAGCATCTGCC
ACAATAATAGACTATAAAACAGGCCATGTTAAGGCTTTAGTTGGAGGAAGAGGGGAACAA
CCTGCTATGTCTCACAATAGAGCTTATTATGATTTAAAATCTATAGGTTCTGCAACAAAA
CCATTAACAGTTTATGGTCCTGCTATTGATTTAGGACTTGGTGGCGCTGGCTCTGTAGTA
AATGATTCTCCATTAAGTAATAAAGAGTTATCTTCTACAGGATATAAAGATCAACCTAAG
AATGAATACAATAGTTATAGAGGCCCTTTAACTTTTAGAGAAGCAATTAAAATCTCTAGT
AACTTAGCAGCCATAAAAGTTGCTAATGAAGTAGGTGTTTCAAACTCTATAGCTTATGGA
GAAAAATTAGGTCTTGTTTATGGACCTCATTCTAGAGGTATTTCCACAACAGCCTTAGGT
CAATTCCAAAATGACCCTAATAATCCTGATGGAGGAAATACTTATACTCTAGCTTCAGCC
TTCGGTGTTTTTGGTAATAACGGTGTTAAAACAAATGCTAAATTATATACAAAGGTATTA
GATTCTCATGGAAATGTAATTCTTGATACAAGTACTCCAGAAGAAACTAAAATATTTAGT
CCTCAAGCGTCTTATATAGTTTATGATATGCTTAAGGATCAAGTAGAAAGTGGCTCTGCA
AAATCTGCTAAATTTGGTAATATTCCTGTGGCGGGTAAAACAGGAACTACTACTGGAGAT
AAAGACTATTTATTTGCAGGATTAACTCCATATTATTCTGCGGCTATTTGGATTGGATAT
GATAAGCCTAGAGAAATGAGAACTAGTAGTGGTACTGTTACCTCTCCTATTTTCGGAAAA
ATAATGGGCTTAGCTCATAAAGACTTACAGTACAAAGAGGTTGACAACCTAGTGGAATAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Shimizu T, Ohtani K, Hirakawa H, Ohshima K, Yamashita A, Shiba T, Ogasawara N, Hattori M, Kuhara S, Hayashi H: Complete genome sequence of Clostridium perfringens, an anaerobic flesh-eater. Proc Natl Acad Sci U S A. 2002 Jan 22;99(2):996-1001. Epub 2002 Jan 15. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 1539
Target 2 Name Oligopeptide transporter, small intestine isoform
Target 2 Synonyms
  1. Intestinal H(+)/peptide cotransporter
  2. Peptide transporter 1
  3. Solute carrier family 15 member 1
Target 2 Gene Name SLC15A1
Target 2 Protein Sequence >Oligopeptide transporter, small intestine isoform 
MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDNLSTAIYHTFV
ALCYLTPILGALIADSWLGKFKTIVSLSIVYTIGQAVTSVSSINDLTDHNHDGTPDSLPV
HVVLSLIGLALIALGTGGIKPCVSAFGGDQFEEGQEKQRNRFFSIFYLAINAGSLLSTII
TPMLRVQQCGIHSKQACYPLAFGVPAALMAVALIVFVLGSGMYKKFKPQGNIMGKVAKCI
GFAIKNRFRHRSKAFPKREHWLDWAKEKYDERLISQIKMVTRVMFLYIPLPMFWALFDQQ
GSRWTLQATTMSGKIGALEIQPDQMQTVNAILIVIMVPIFDAVLYPLIAKCGFNFTSLKK
MAVGMVLASMAFVVAAIVQVEIDKTLPVFPKGNEVQIKVLNIGNNTMNISLPGEMVTLGP
MSQTNAFMTFDVNKLTRINISSPGSPVTAVTDDFKQGQRHTLLVWAPNHYQVVKDGLNQK
PEKGENGIRFVNTFNELITITMSGKVYANISSYNASTYQFFPSGIKGFTISSTEIPPQCQ
PNFNTFYLEFGSAYTYIVQRKNDSCPEVKVFEDISANTVNMALQIPQYFLLTCGEVVFSV
TGLEFSYSQAPSNMKSVLQAGWLLTVAVGNIIVLIVAGAGQFSKQWAEYILFAALLLVVC
VIFAIMARFYTYINPAEIEAQFDEDEKKNRLEKSNPYFMSGANSQKQM
Target 2 Number of Residues 719
Target 2 Molecular Weight 78807
Target 2 Theoretical pI 8.64
Target 2 GO Classification
Function
transporter activity
peptide transporter activity
oligopeptide transporter activity
Process
physiological process
cellular physiological process
transport
peptide transport
oligopeptide transport
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 2 General Function Amino acid transport and metabolism
Target 2 Specific Function Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 1-21
  • 54-74
  • 83-103
  • 119-139
  • 162-182
  • 199-219
  • 277-297
  • 328-348
  • 362-382
  • 585-605
  • 620-640
  • 646-666
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 773588 Link Image
Target 2 UniProtKB/Swiss-Prot ID P46059 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name S15A1_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 2 Gene Sequence >2127 bp 
ATGGGAATGTCCAAATCACACAGTTTCTTTGGTTATCCCCTGAGCATCTTCTTCATCGTG
GTCAATGAGTTTTGCGAAAGATTTTCCTACTATGGAATGCGAGCAATCCTGATTCTGTAC
TTCACAAATTTCATCAGCTGGGATGATAACCTGTCCACCGCCATCTACCATACGTTTGTG
GCTCTGTGCTACCTGACGCCAATTCTCGGAGCTCTTATCGCCGACTCGTGGCTGGGAAAG
TTCAAGACCATTGTGTCGCTCTCCATTGTCTACACAATTGGACAAGCAGTCACCTCAGTA
AGCTCCATTAATGACCTCACAGACCACAACCATGATGGCACCCCCGACAGCCTTCCTGTG
CACGTGGTGCTGTCCTTGATCGGCCTGGCCCTGATAGCTCTCGGGACTGGAGGAATCAAA
CCCTGTGTGTCTGCGTTTGGTGGAGATCAGTTTGAAGAGGGCCAGGAGAAACAAAGAAAC
AGATTTTTTTCCATCTTTTACTTGGCTATTAATGCTGGAAGTTTGCTTTCCACAATCATC
ACACCCATGCTCAGAGTTCAACAATGTGGAATTCACAGTAAACAAGCTTGTTACCCACTG
GCCTTTGGGGTTCCTGCTGCTCTCATGGCTGTAGCCCTGATTGTGTTTGTCCTTGGCAGT
GGGATGTACAAGAAGTTCAAGCCACAGGGCAACATCATGGGTAAAGTGGCCAAGTGCATC
GGTTTTGCCATCAAAAATAGATTTAGGCATCGGAGTAAGGCATTTCCCAAGAGGGAGCAC
TGGCTGGACTGGGCTAAAGAGAAATACGATGAGCGGCTCATCTCCCAAATTAAGATGGTT
ACGAGGGTGATGTTCCTGTATATTCCACTCCCAATGTTCTGGGCCTTGTTTGACCAGCAG
GGCTCCAGGTGGACACTGCAGGCAACAACTATGTCCGGGAAAATCGGAGCTCTTGAAATT
CAGCCCGATCAGATGCAGACCGTGAACGCCATCCTGATCGTGATCATGGTCCCGATCTTC
GATGCTGTGCTGTACCCTCTCATTGCAAAATGTGGCTTCAATTTCACCTCCTTGAAGAAG
ATGGCAGTTGGCATGGTCCTGGCCTCCATGGCCTTTGTGGTGGCTGCCATCGTGCAGGTG
GAAATCGATAAAACTCTTCCAGTCTTCCCCAAAGGAAACGAAGTCCAAATTAAAGTTTTG
AATATAGGAAACAATACCATGAATATATCTCTTCCTGGAGAGATGGTGACACTTGGCCCA
ATGTCTCAAACAAATGCATTTATGACTTTTGATGTAAACAAACTGACAAGGATAAACATT
TCTTCTCCTGGATCACCAGTCACTGCTGTAACTGACGACTTCAAGCAGGGCCAACGCCAC
ACGCTTCTAGTGTGGGCCCCCAATCACTACCAGGTGGTAAAGGATGGTCTTAACCAGAAG
CCAGAAAAAGGGGAAAATGGAATCAGATTTGTAAATACTTTTAACGAGCTCATCACCATC
ACAATGAGTGGGAAAGTTTATGCAAACATCAGCAGCTACAATGCCAGCACATACCAGTTT
TTTCCTTCTGGCATAAAAGGCTTCACAATAAGCTCAACAGAGATTCCGCCACAATGTCAA
CCTAATTTCAATACTTTCTACCTTGAATTTGGTAGTGCTTATACCTATATAGTCCAAAGG
AAGAATGACAGCTGCCCTGAAGTGAAGGTGTTTGAAGATATTTCAGCCAACACAGTTAAC
ATGGCTCTGCAAATCCCGCAGTATTTTCTTCTCACCTGTGGCGAAGTGGTCTTCTCTGTC
ACGGGATTGGAATTCTCATATTCTCAGGCTCCTTCCAACATGAAGTCGGTGCTTCAGGCA
GGATGGCTGCTGACCGTGGCTGTTGGCAACATCATTGTGCTCATCGTGGCAGGGGCAGGC
CAGTTCAGCAAACAGTGGGCCGAGTACATTCTATTTGCCGCGTTGCTTCTGGTCGTCTGT
GTAATTTTTGCCATCATGGCTCGGTTCTATACTTACATCAACCCAGCGGAGATCGAAGCT
CAATTTGATGAGGATGAAAAGAAAAACAGACTGGAAAAGAGTAACCCATATTTCATGTCA
GGGGCCAATTCACAGAAACAGATGTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID SLC15A1 Link Image
Target 2 GenAtlas ID SLC15A1 Link Image
Target 2 HGNC ID HGNC:10920 Link Image
Target 2 Chromosome Location 13
Target 2 Locus 13q33-q34
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Liang R, Fei YJ, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH: Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization. J Biol Chem. 1995 Mar 24;270(12):6456-63. [PubMed Link Image]
Target 2 Drug References
  1. Tsuda M, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K: 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. Epub 2006 Apr 5. [PubMed Link Image]
  2. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed Link Image]
  3. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed Link Image]
  4. Bretschneider B, Brandsch M, Neubert R: Intestinal transport of beta-lactam antibiotics: analysis of the affinity at the H+/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res. 1999 Jan;16(1):55-61. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.