APALCILLIN SODIUM

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H22N5O6S.Na
Molecular Weight	543.527
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)C3=CN=C4C=CC=NC4=C3O)C5=CC=CC=C5)C(=O)N2[C@H]1C([O-])=O

InChI

InChIKey=DIGBQDMXLUJMHN-FSWJYKAZSA-M

InChI=1S/C25H23N5O6S.Na/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);/q;+1/p-1/t15-,17-,19+,23-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C25H22N5O6S
Molecular Weight	520.537
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3415216 | https://www.ncbi.nlm.nih.gov/pubmed/6421745 | https://www.ncbi.nlm.nih.gov/pubmed/3871382 | https://www.ncbi.nlm.nih.gov/pubmed/2797878

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

Title	Date	PubMed
The pharmacokinetics of the interstitial space in humans.	2003-07-30	12890292

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:59 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:59 GMT 2025`
Record UNII	3XQ12NYC0Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APALCILLIN SODIUM SALT

Preferred Name

English

APALCILLIN SODIUM

Official Name

English

WY-44,417 SODIUM

Code

English

APALCILLIN SODIUM [USAN]

Common Name

English

APALCILLIN SODIUM SALT [MI]

Common Name

English

Sodium (2S,5R,6R)-6-[(R)-2-(4-hydroxy-1,5-naphthyridine-3-carboxamido)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Systematic Name

English

APALCILLIN SODIUM [MART.]

Common Name

English

WY-44417 SODIUM

Code

English

APALCILLIN SODIUM [JAN]

Common Name

English

Apalcillin sodium [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500