Identification

Name
Azidocillin
Accession Number
DB08795
Type
Small Molecule
Groups
Approved
Description

Azidocillin is a penicillin antibiotic similir to ampicillin.

Structure
Thumb
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][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](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

Structured Indications
Not Available
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.

TargetActionsOrganism
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B
inhibitor
Streptococcus 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
DrugInteractionDrug group
AcenocoumarolAzidocillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Azidocillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Azidocillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Azidocillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Azidocillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Azidocillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Azidocillin.Approved, Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Azidocillin.Experimental
ChlortetracyclineThe therapeutic efficacy of Azidocillin can be decreased when used in combination with Chlortetracycline.Approved, Investigational, Vet Approved
ClorindioneAzidocillin may increase the anticoagulant activities of Clorindione.Experimental
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Azidocillin.Approved
DemeclocyclineThe therapeutic efficacy of Azidocillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Azidocillin.Experimental
DicoumarolAzidocillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Azidocillin.Investigational, Vet Approved
DiphenadioneAzidocillin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Azidocillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Azidocillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Azidocillin.Approved
Ethyl biscoumacetateAzidocillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneAzidocillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Azidocillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Azidocillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Azidocillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Azidocillin.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Azidocillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Azidocillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Azidocillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Azidocillin.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Azidocillin.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Azidocillin.Approved, Investigational, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Azidocillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Azidocillin.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Azidocillin.Experimental
MinocyclineThe therapeutic efficacy of Azidocillin can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe 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
NeamineThe serum concentration of Neamine can be decreased when it is combined with Azidocillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Azidocillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Azidocillin.Approved, Investigational
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Azidocillin.Approved, Investigational
PhenindioneAzidocillin may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonAzidocillin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Azidocillin.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Azidocillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Azidocillin.Approved, Investigational, Withdrawn
ProbenecidThe serum concentration of Azidocillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Azidocillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Azidocillin.Approved, Investigational
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Azidocillin.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Azidocillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Azidocillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Azidocillin.Approved, Investigational, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Azidocillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Azidocillin.Approved
TioclomarolAzidocillin may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Azidocillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Azidocillin.Approved
WarfarinAzidocillin may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Azidocillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Azidocillin.Experimental
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15685
PubChem Compound
15574941
PubChem Substance
99445265
ChemSpider
16735689
ChEBI
51758
ChEMBL
CHEMBL2105907
PharmGKB
PA165958414
Wikipedia
Azidocillin
ATC Codes
J01CR50 — Combinations of penicillinsJ01CE04 — Azidocillin

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.611 mg/mLALOGPS
logP2.32ALOGPS
logP1.19ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.14 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity92.16 m3·mol-1ChemAxon
Polarizability35.87 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9568
Blood Brain Barrier-0.9909
Caco-2 permeable-0.6798
P-glycoprotein substrateSubstrate0.5299
P-glycoprotein inhibitor INon-inhibitor0.9435
P-glycoprotein inhibitor IINon-inhibitor0.9823
Renal organic cation transporterNon-inhibitor0.9499
CYP450 2C9 substrateNon-substrate0.7411
CYP450 2D6 substrateNon-substrate0.8389
CYP450 3A4 substrateNon-substrate0.5507
CYP450 1A2 substrateNon-inhibitor0.8146
CYP450 2C9 inhibitorNon-inhibitor0.817
CYP450 2D6 inhibitorNon-inhibitor0.9089
CYP450 2C19 inhibitorNon-inhibitor0.8013
CYP450 3A4 inhibitorNon-inhibitor0.8838
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.969
Ames testNon AMES toxic0.643
CarcinogenicityNon-carcinogens0.5599
BiodegradationNot ready biodegradable0.8894
Rat acute toxicity2.1329 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9987
hERG inhibition (predictor II)Non-inhibitor0.9125
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. 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]
  2. 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 November 09, 2017 04:40