U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H23N5O6S
Molecular Weight 521.545
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APALCILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)C3=CN=C4C=CC=NC4=C3O)C5=CC=CC=C5)C(O)=O

InChI

InChIKey=XMQVYNAURODYCQ-SLFBBCNNSA-N
InChI=1S/C25H23N5O6S/c1-25(2)19(24(35)36)30-22(34)17(23(30)37-25)29-21(33)15(12-7-4-3-5-8-12)28-20(32)13-11-27-14-9-6-10-26-16(14)18(13)31/h3-11,15,17,19,23H,1-2H3,(H,27,31)(H,28,32)(H,29,33)(H,35,36)/t15-,17-,19+,23-/m1/s1

HIDE SMILES / InChI
Apalcillin is a naphthydridine derivative of ampicillin. Apalcillin has a broad spectrum of antibacterial activity that is very similar to that of piperacillin, except that apalcillin is significantly more active against Pseudomonas aeruginosa and Acinetobacter spp. Against Acinetobacter spp., apalcillin is uniquely active, compared to the other penicillins and comparison drugs. Strains producing high amounts of β-lactamases do become resistant to apalcillin. PAH (p-aminohippurate) clearance was significantly decreased during apalcillin infusion. Apalcillin appeared to compete with PAH for proximal tubular secretion but induced no further renal dysfunction.

Approval Year

PubMed

PubMed

TitleDatePubMed
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
Patents
Name Type Language
APALCILLIN
INN   MI   WHO-DD  
INN  
Official Name English
APALCILLIN [MI]
Common Name English
apalcillin [INN]
Common Name English
Apalcillin [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
Code System Code Type Description
MERCK INDEX
m1980
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C76217
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID60101650
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
CHEBI
51691
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
EVMPD
SUB05535MIG
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL3306902
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
DRUG CENTRAL
227
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
INN
4422
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
FDA UNII
3373RT9U7A
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
MESH
C012122
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
SMS_ID
100000086956
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
PUBCHEM
6602341
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY
CAS
63469-19-2
Created by admin on Fri Dec 15 16:32:50 GMT 2023 , Edited by admin on Fri Dec 15 16:32:50 GMT 2023
PRIMARY