(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-(−)-(α-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	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

Drug	Interaction
(R)-warfarin	Azidocillin may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin	Azidocillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarin	Azidocillin may increase the anticoagulant activities of 4-hydroxycoumarin.
Acemetacin	Acemetacin may decrease the excretion rate of Azidocillin which could result in a higher serum level.
Acenocoumarol	Azidocillin may increase the anticoagulant activities of Acenocoumarol.
Adenovirus type 7 vaccine live	The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Azidocillin.
Alcuronium	The therapeutic efficacy of Alcuronium can be increased when used in combination with Azidocillin.
Amikacin	The serum concentration of Amikacin can be decreased when it is combined with Azidocillin.
Anthrax immune globulin human	The therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Azidocillin.
Anthrax vaccine	The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Azidocillin.

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

J01CE04 — 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

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	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

Details1. 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]

Details2. 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]

Details3. 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]

Details4. 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]

Details5. 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

Details1. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
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]

Details2. Solute carrier family 15 member 1

Kind: Protein
Organism: Humans
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]

Details3. Solute carrier family 15 member 2

Kind: Protein
Organism: Humans
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 December 14, 2018 05:41

Azidocillin

Identification

Structure for Azidocillin (DB08795)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

References

References

Transporters

References

References

References