Jump to section
IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Azidocillin
- Accession Number
- DB08795
- Type
- Small Molecule
- Groups
- Approved
- Description
Azidocillin is a penicillin antibiotic similir to ampicillin.
- Structure
Structure for DB08795 (Azidocillin)
- Synonyms
- (2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- Azidocilina
- Azidocilline
- Azidocillinum
- D-(-)-(alpha-Azidobenzyl)penicillin
- External IDs
- BRL 2534 / BRL-2534 / SPC 297 D / SPC-297-D
- International/Other Brands
- Alocillin (Panbiotic) / Alocin (Conba) / Azlocillin (Balkanpharma)
- Categories
- UNII
- R8XDP7L3SL
- CAS number
- 17243-38-8
- Weight
- Average: 375.402
Monoisotopic: 375.100124747 - Chemical Formula
- C16H17N5O4S
- InChI Key
- ODFHGIPNGIAMDK-NJBDSQKTSA-N
- InChI
- InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1
- IUPAC Name
- (2S,5R,6R)-6-[(2R)-2-azido-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O
Pharmacology
- Indication
For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
- Pharmacodynamics
- Not Available
- Mechanism of action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Azidocillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Azidocillin interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 2a inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 1b inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 3 inhibitorStreptococcus pneumoniae APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half life
- Not Available
- Clearance
- Not Available
- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Acenocoumarol Azidocillin may increase the anticoagulant activities of Acenocoumarol. Approved, Investigational Amikacin The serum concentration of Amikacin can be decreased when it is combined with Azidocillin. Approved, Investigational, Vet Approved Apramycin The serum concentration of Apramycin can be decreased when it is combined with Azidocillin. Experimental, Vet Approved Arbekacin The serum concentration of Arbekacin can be decreased when it is combined with Azidocillin. Approved, Investigational Bekanamycin The serum concentration of Bekanamycin can be decreased when it is combined with Azidocillin. Experimental Chlortetracycline The therapeutic efficacy of Azidocillin can be decreased when used in combination with Chlortetracycline. Approved, Investigational, Vet Approved Clorindione Azidocillin may increase the anticoagulant activities of Clorindione. Experimental Demeclocycline The therapeutic efficacy of Azidocillin can be decreased when used in combination with Demeclocycline. Approved Dibekacin The serum concentration of Dibekacin can be decreased when it is combined with Azidocillin. Experimental Dicoumarol Azidocillin may increase the anticoagulant activities of Dicoumarol. Approved Dihydrostreptomycin The serum concentration of Dihydrostreptomycin can be decreased when it is combined with Azidocillin. Investigational, Vet Approved Diphenadione Azidocillin may increase the anticoagulant activities of Diphenadione. Experimental Doxycycline The therapeutic efficacy of Azidocillin can be decreased when used in combination with Doxycycline. Approved, Investigational, Vet Approved Ethyl biscoumacetate Azidocillin may increase the anticoagulant activities of Ethyl biscoumacetate. Withdrawn Fluindione Azidocillin may increase the anticoagulant activities of Fluindione. Approved, Investigational Framycetin The serum concentration of Framycetin can be decreased when it is combined with Azidocillin. Approved Geneticin The serum concentration of Geneticin can be decreased when it is combined with Azidocillin. Experimental Gentamicin The serum concentration of Gentamicin can be decreased when it is combined with Azidocillin. Approved, Vet Approved GENTAMICIN C1A The serum concentration of GENTAMICIN C1A can be decreased when it is combined with Azidocillin. Experimental Hygromycin B The serum concentration of Hygromycin B can be decreased when it is combined with Azidocillin. Vet Approved Isepamicin The serum concentration of Isepamicin can be decreased when it is combined with Azidocillin. Experimental Kanamycin The serum concentration of Kanamycin can be decreased when it is combined with Azidocillin. Approved, Investigational, Vet Approved Methotrexate The serum concentration of Methotrexate can be increased when it is combined with Azidocillin. Approved Micronomicin The serum concentration of Micronomicin can be decreased when it is combined with Azidocillin. Experimental Minocycline The therapeutic efficacy of Azidocillin can be decreased when used in combination with Minocycline. Approved, Investigational Mycophenolic acid The serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Azidocillin resulting in a loss in efficacy. Approved Neamine The serum concentration of Neamine can be decreased when it is combined with Azidocillin. Experimental Neomycin The serum concentration of Neomycin can be decreased when it is combined with Azidocillin. Approved, Vet Approved Netilmicin The serum concentration of Netilmicin can be decreased when it is combined with Azidocillin. Approved, Investigational Oxytetracycline The therapeutic efficacy of Azidocillin can be decreased when used in combination with Oxytetracycline. Approved, Investigational, Vet Approved Paromomycin The serum concentration of Paromomycin can be decreased when it is combined with Azidocillin. Approved, Investigational Phenindione Azidocillin may increase the anticoagulant activities of Phenindione. Approved, Investigational Phenprocoumon Azidocillin may increase the anticoagulant activities of Phenprocoumon. Approved, Investigational Plazomicin The serum concentration of Plazomicin can be decreased when it is combined with Azidocillin. Approved, Investigational Probenecid The serum concentration of Azidocillin can be increased when it is combined with Probenecid. Approved, Investigational Puromycin The serum concentration of Puromycin can be decreased when it is combined with Azidocillin. Experimental Ribostamycin The serum concentration of Ribostamycin can be decreased when it is combined with Azidocillin. Approved, Investigational Sisomicin The serum concentration of Sisomicin can be decreased when it is combined with Azidocillin. Investigational Streptomycin The serum concentration of Streptomycin can be decreased when it is combined with Azidocillin. Approved, Vet Approved Tetracycline The therapeutic efficacy of Azidocillin can be decreased when used in combination with Tetracycline. Approved, Vet Approved Tioclomarol Azidocillin may increase the anticoagulant activities of Tioclomarol. Experimental Tobramycin The serum concentration of Tobramycin can be decreased when it is combined with Azidocillin. Approved, Investigational Warfarin Azidocillin may increase the anticoagulant activities of Warfarin. Approved - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015685
- PubChem Compound
- 15574941
- PubChem Substance
- 99445265
- ChemSpider
- 16735689
- ChEBI
- 51758
- ChEMBL
- CHEMBL2105907
- PharmGKB
- PA165958414
- Wikipedia
- Azidocillin
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.611 mg/mL ALOGPS logP 2.32 ALOGPS logP 1.19 ChemAxon logS -2.8 ALOGPS pKa (Strongest Acidic) 3.32 ChemAxon pKa (Strongest Basic) -6.4 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 116.14 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 92.16 m3·mol-1 ChemAxon Polarizability 35.87 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption - 0.9568 Blood Brain Barrier - 0.9909 Caco-2 permeable - 0.6798 P-glycoprotein substrate Substrate 0.5299 P-glycoprotein inhibitor I Non-inhibitor 0.9435 P-glycoprotein inhibitor II Non-inhibitor 0.9823 Renal organic cation transporter Non-inhibitor 0.9499 CYP450 2C9 substrate Non-substrate 0.7411 CYP450 2D6 substrate Non-substrate 0.8389 CYP450 3A4 substrate Non-substrate 0.5507 CYP450 1A2 substrate Non-inhibitor 0.8146 CYP450 2C9 inhibitor Non-inhibitor 0.817 CYP450 2D6 inhibitor Non-inhibitor 0.9089 CYP450 2C19 inhibitor Non-inhibitor 0.8013 CYP450 3A4 inhibitor Non-inhibitor 0.8838 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.969 Ames test Non AMES toxic 0.643 Carcinogenicity Non-carcinogens 0.5599 Biodegradation Not ready biodegradable 0.8894 Rat acute toxicity 2.1329 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9987 hERG inhibition (predictor II) Non-inhibitor 0.9125
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Penicillins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Phenylacetamides / Thiazolidines / Tertiary carboxylic acid amides / Azetidines / Secondary carboxylic acid amides / Azo compounds / Azo imides / Azacyclic compounds / Thiohemiaminal derivatives show 7 more
- Substituents
- Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Phenylacetamide / Monocyclic benzene moiety / Benzenoid / Thiazolidine / Tertiary carboxylic acid amide / Azetidine / Secondary carboxylic acid amide show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:51758)
Targets
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Not Available
- Gene Name
- pbp2a
- Uniprot ID
- Q8DNB6
- Uniprot Name
- Penicillin-binding protein 2a
- Molecular Weight
- 80797.94 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Not Available
- Gene Name
- pbp1b
- Uniprot ID
- Q7CRA4
- Uniprot Name
- Penicillin-binding protein 1b
- Molecular Weight
- 89479.92 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Not Available
- Gene Name
- pbp3
- Uniprot ID
- Q75Y35
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 45209.84 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Cell wall formation.
- Gene Name
- pbpA
- Uniprot ID
- Q8DR59
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M6
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- 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.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326]
- Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
- 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:9374833]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- 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:9374833]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
Drug created on October 08, 2010 15:48 / Updated on July 02, 2018 19:07