LENAMPICILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H23N3O7S
Molecular Weight	461.488
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)OCC4=C(C)OC(=O)O4

InChI

InChIKey=ZKUKMWMSYCIYRD-ZXFNITATSA-N

InChI=1S/C21H23N3O7S/c1-10-12(31-20(28)30-10)9-29-19(27)15-21(2,3)32-18-14(17(26)24(15)18)23-16(25)13(22)11-7-5-4-6-8-11/h4-8,13-15,18H,9,22H2,1-3H3,(H,23,25)/t13-,14-,15+,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H23N3O7S
Molecular Weight	461.488
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4053214

Lenampicillin is a prodrug of ampicillin that inhibits bacterial penicillin binding proteins (transpeptidase) and thus is effective against a wide range of bacterial infections. The drug was developed and marketed in Japan (Takacillin, Varacillin), however its current marketing status is unknown and supposed to be discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2683579	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://apps.who.int/medicinedocs/documents/h5776e/h5776e.pdf	Curative		Approved 8429	TAKACILLIN Approved Use Various infections including respiratory, urinary tract, skin and soft tissue, surgical, otolaryngological, ophthalmological and dental infections due to susceptible microorganism

PubMed

Title	Date	PubMed
Non-mutagenicity of KBT-1585, a novel ester of ampicillin.	1984 Feb	6399011
Single- and multiple-dose pharmacokinetics of lenampicillin (KBT-1585) in healthy human subjects: comparative studies with amoxicillin.	1985 Aug	4053214
[Clinical evaluation of lenampicillin in the treatment of superficial suppurative skin and soft tissue infection. A double-blind study comparing amoxicillin].	1985 Jul	3906167
[Metabolism of lenampicillin hydrochloride. I. Metabolism of ampicillin structure].	1985 Jul	4068220
[Comparative study of the effectiveness of lenampicillin and bacampicillin on bacterial pneumonia by double blind method].	1985 Jun	3932547
[Clinical studies on lenampicillin in the therapy of skin and soft tissue infections].	1985 Jun	4046172
Pharmacokinetic study of lenampicillin (KBT-1585) in healthy volunteers.	1986 May	3729355
A comparative pharmacokinetic study between lenampicillin, bacampicillin and amoxycillin.	1989 Jul	16312500
Concentrations of ampicillin in human serum and mixed saliva following a single oral administration of lenampicillin, and relationship between serum and mixed saliva concentrations.	1990 Mar	2345375
High-performance liquid chromatographic assay of ampicillin and its prodrug lenampicillin.	1990 May 16	2380291
Ampicillin concentrations in human oral tissues following a single oral administration of lenampicillin.	1991	1761182
Differences in postoperative morbidity rates, including infection and dry socket, and differences in the healing process after mandibular third molar surgery in patients receiving 1-day or 3-day prophylaxis with lenampicillin.	2002 Mar	11957126
Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine.	2010 Apr 16	20177059

Patents

Sample Use Guides

In Vivo Use Guide

1,000 mg, in 4 equally divided doses

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:45:17 GMT 2023` Edited by `admin` on `Sat Dec 16 17:45:17 GMT 2023`
Record UNII	8M568DM08K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LENAMPICILLIN

Official Name

English

lenampicillin [INN]

Common Name

English

2,3-DIHYDROXY-2-BUTENYL(2S,5R,6R)-6-((R)-2-AMINO-2-PHENYLACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE, CYCLIC CARBONATE

Common Name

English

Lenampicillin [WHO-DD]

Common Name

English

LENAMPICILLIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500