Azidocillin - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (5)Transporters (3)

Targets (5)Transporters (3)Biointeractions (8)

Identification

Name

Azidocillin

Accession Number

DB08795

Type

Small Molecule

Groups

Approved

Description

Azidocillin is a penicillin antibiotic similir to ampicillin.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Alocillin	Panbiotic
Alocin	Conba
Azlocillin	Balkanpharma

Brand mixtures

Not Available

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Penicillin-binding protein 2a	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Q8DNB6	details
Penicillin-binding protein 1b	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Q7CRA4	details
Penicillin-binding protein 3	Protein	yes	inhibitor	Streptococcus pneumoniae	Q75Y35	details
Penicillin-binding protein 1A	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Q8DR59	details
Penicillin-binding protein 2B	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	P0A3M6	details

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
Aclarubicin	The serum concentration of Aclarubicin can be decreased when it is combined with Azidocillin.	Investigational
Amikacin	The serum concentration of Amikacin can be decreased when it is combined with Azidocillin.	Approved, Vet Approved
Amrubicin	The serum concentration of Amrubicin can be decreased when it is combined with Azidocillin.	Approved, Investigational
annamycin	The serum concentration of annamycin can be decreased when it is combined with Azidocillin.	Investigational
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
Chlortetracycline	The therapeutic efficacy of Azidocillin can be decreased when used in combination with Chlortetracycline.	Approved, Vet Approved
Daunorubicin	The serum concentration of Daunorubicin can be decreased when it is combined with Azidocillin.	Approved
Demeclocycline	The therapeutic efficacy of Azidocillin can be decreased when used in combination with Demeclocycline.	Approved
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.	Vet Approved
Doxorubicin	The serum concentration of Doxorubicin can be decreased when it is combined with Azidocillin.	Approved, Investigational
Doxycycline	The therapeutic efficacy of Azidocillin can be decreased when used in combination with Doxycycline.	Approved, Investigational, Vet Approved
Epirubicin	The serum concentration of Epirubicin can be decreased when it is combined with Azidocillin.	Approved
Ethyl biscoumacetate	Azidocillin may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Fluindione	Azidocillin may increase the anticoagulant activities of Fluindione.	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
Idarubicin	The serum concentration of Idarubicin can be decreased when it is combined with Azidocillin.	Approved
INNO-206	The serum concentration of INNO-206 can be decreased when it is combined with Azidocillin.	Investigational
Kanamycin	The serum concentration of Kanamycin can be decreased when it is combined with Azidocillin.	Approved, Vet Approved
Methotrexate	The serum concentration of Methotrexate can be increased when it is combined with Azidocillin.	Approved
Metrizamide	The serum concentration of Metrizamide can be decreased when it is combined with Azidocillin.	Approved
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
Oxytetracycline	The therapeutic efficacy of Azidocillin can be decreased when used in combination with Oxytetracycline.	Approved, 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
Phenprocoumon	Azidocillin may increase the anticoagulant activities of Phenprocoumon.	Approved
Pirarubicin	The serum concentration of Pirarubicin can be decreased when it is combined with Azidocillin.	Investigational
Plicamycin	The serum concentration of Plicamycin can be decreased when it is combined with Azidocillin.	Approved, Withdrawn
Probenecid	The serum concentration of Azidocillin can be increased when it is combined with Probenecid.	Approved
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
Sisomicin	The serum concentration of Sisomicin can be decreased when it is combined with Azidocillin.	Investigational
SP1049C	The serum concentration of SP1049C can be decreased when it is combined with Azidocillin.	Investigational
Spectinomycin	The serum concentration of Spectinomycin can be decreased when it is combined with Azidocillin.	Approved, Vet Approved
Streptomycin	The serum concentration of Streptomycin can be decreased when it is combined with Azidocillin.	Approved, Vet Approved
Streptozocin	The serum concentration of Streptozocin can be decreased when it is combined with Azidocillin.	Approved
Tetracycline	The therapeutic efficacy of Azidocillin can be decreased when used in combination with Tetracycline.	Approved, Vet Approved
Tobramycin	The serum concentration of Tobramycin can be decreased when it is combined with Azidocillin.	Approved, Investigational
Valrubicin	The serum concentration of Valrubicin can be decreased when it is combined with Azidocillin.	Approved
Warfarin	Azidocillin may increase the anticoagulant activities of Warfarin.	Approved
Zorubicin	The serum concentration of Zorubicin can be decreased when it is combined with Azidocillin.	Experimental

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15685
PubChem Compound	15574941
PubChem Substance	99445265
ChemSpider	16735689
ChEBI	51758
ChEMBL	CHEMBL2105907
PharmGKB	PA165958414
Wikipedia	Azidocillin

ATC Codes

J01CR50 — Combinations of penicillins

J01CE04 — Azidocillin

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

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

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:51758 )

Targets

Details

1. Penicillin-binding protein 2a

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 ]

Details

2. Penicillin-binding protein 1b

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 ]

Details

3. Penicillin-binding protein 3

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 ]

Details

4. Penicillin-binding protein 1A

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 ]

Details

5. Penicillin-binding protein 2B

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

Details

1. Solute carrier family 22 member 5

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 cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
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 ]

Details

2. Solute carrier family 15 member 1

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 ]

Details

3. Solute carrier family 15 member 2

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 September 01, 2017 11:58

Structure for DB08795 (Azidocillin)

Targets

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Transporters

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