LENAMPICILLIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H23N3O7S.ClH
Molecular Weight	497.949
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LENAMPICILLIN HYDROCHLORIDE

Structure Search

SMILES

Cl.CC1=C(COC(=O)[C@@H]2N3[C@H](SC2(C)C)[C@H](NC(=O)[C@H](N)C4=CC=CC=C4)C3=O)OC(=O)O1

InChI

InChIKey=FXXSETTYJSGMCR-GLCLSGQWSA-N

InChI=1S/C21H23N3O7S.ClH/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);1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
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/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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2683579	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://apps.who.int/medicinedocs/documents/h5776e/h5776e.pdf	Curative		Approved 8583	TAKACILLIN Approved Use Various infections including respiratory, urinary tract, skin and soft tissue, surgical, otolaryngological, ophthalmological and dental infections due to susceptible microorganism

C_max

Value	Dose	Analyte	Population
12 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2759930/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg 4 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg 4 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
21.8 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2759930/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
19.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg 4 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg 4 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2759930/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.61 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.83 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
0.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg 4 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg 4 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729355/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	AMPICILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
70% EXPERIMENT https://www.jstage.jst.go.jp/article/chemotherapy1953/32/Supplement8/32_Supplement8_181/_article/-char/ja/			LENAMPICILLIN serum	Homo sapiens

Doses

Dose	Population	Adverse events
1000 mg 4 times / day multiple, oral Highest studied dose Dose: 1000 mg, 4 times / day Route: oral Route: multiple Dose: 1000 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/	Other AEs: Diarrhea, Eruption... Other AEs: Diarrhea (grade 1-2, 2%) Eruption (grade 1, 1%) Hoarseness (grade 2, 1%) Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/
3000 mg single, oral Highest studied dose Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: https://www.jstage.jst.go.jp/article/chemotherapy1953/32/Supplement8/32_Supplement8_542/_article/-char/ja/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://www.jstage.jst.go.jp/article/chemotherapy1953/32/Supplement8/32_Supplement8_542/_article/-char/ja/	Sources: https://www.jstage.jst.go.jp/article/chemotherapy1953/32/Supplement8/32_Supplement8_542/_article/-char/ja/

AEs

AE	Significance	Dose	Population
Eruption	grade 1, 1%	1000 mg 4 times / day multiple, oral Highest studied dose Dose: 1000 mg, 4 times / day Route: oral Route: multiple Dose: 1000 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/
Diarrhea	grade 1-2, 2%	1000 mg 4 times / day multiple, oral Highest studied dose Dose: 1000 mg, 4 times / day Route: oral Route: multiple Dose: 1000 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/
Hoarseness	grade 2, 1%	1000 mg 4 times / day multiple, oral Highest studied dose Dose: 1000 mg, 4 times / day Route: oral Route: multiple Dose: 1000 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3932547/

PubMed

Title	Date	PubMed
Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine.	2010-04-16	20177059
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.	2002-03	11957126
Ampicillin concentrations in human oral tissues following a single oral administration of lenampicillin.	1991	1761182
High-performance liquid chromatographic assay of ampicillin and its prodrug lenampicillin.	1990-05-16	2380291
Concentrations of ampicillin in human serum and mixed saliva following a single oral administration of lenampicillin, and relationship between serum and mixed saliva concentrations.	1990-03	2345375
A comparative pharmacokinetic study between lenampicillin, bacampicillin and amoxycillin.	1989-07	16312500
Pharmacokinetic study of lenampicillin (KBT-1585) in healthy volunteers.	1986-05	3729355
Single- and multiple-dose pharmacokinetics of lenampicillin (KBT-1585) in healthy human subjects: comparative studies with amoxicillin.	1985-08	4053214
[Clinical evaluation of lenampicillin in the treatment of superficial suppurative skin and soft tissue infection. A double-blind study comparing amoxicillin].	1985-07	3906167
[Metabolism of lenampicillin hydrochloride. I. Metabolism of ampicillin structure].	1985-07	4068220
[Comparative study of the effectiveness of lenampicillin and bacampicillin on bacterial pneumonia by double blind method].	1985-06	3932547
[Clinical studies on lenampicillin in the therapy of skin and soft tissue infections].	1985-06	4046172
Non-mutagenicity of KBT-1585, a novel ester of ampicillin.	1984-02	6399011

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 `Mon Mar 31 21:27:24 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:24 GMT 2025`
Record UNII	6U90E2WB40
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAKACILLIN

Preferred Name

English

LENAMPICILLIN HYDROCHLORIDE

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (5-METHYL-2-OXO-1,3-DIOXOL-4-YL)METHYL ESTER, MONOHYDROCHLORIDE, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-

Common Name

English

KB-1585

Code

English

KBT-1585

Code

English

LENAMPICILLIN HYDROCHLORIDE [JAN]

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2R)-2-AMINO-2-PHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (5-METHYL-2-OXO-1,3-DIOXOL-4-YL)METHYL ESTER, HYDROCHLORIDE (1:1), (2S,5R,6R)-

Common Name

English

LENAMPICILLIN HYDROCHLORIDE [MI]

Common Name

English

VARACILLIN

Brand Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2R)-AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (5-METHYL-2-OXO-1,3-DIOXOL-4-YL)METHYL ESTER, MONOHYDROCHLORIDE, (2S,5R,6R)-

Common Name

English

Lenampicillin hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID0057835