LENAMPICILLIN

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234	Curative		Approved 8,429	TAKACILLIN

C_max

Value	Dose	Analyte	Population
12 mg/L	800 mg single, oral	AMPICILLIN serum	Homo sapiens
5.8 μg/mL	400 mg single, oral	AMPICILLIN serum	Homo sapiens
10.4 μg/mL	800 mg single, oral	AMPICILLIN serum	Homo sapiens
4.9 μg/mL	400 mg 4 times / day multiple, oral	AMPICILLIN serum	Homo sapiens
4.9 μg/mL	400 mg 4 times / day multiple, oral	AMPICILLIN serum	Homo sapiens
6.7 μg/mL	400 mg single, oral	AMPICILLIN serum	Homo sapiens
3.6 μg/mL	400 mg single, oral	AMPICILLIN serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
21.8 mg × h/L	800 mg single, oral	AMPICILLIN serum	Homo sapiens
10.8 μg × h/mL	400 mg single, oral	AMPICILLIN serum	Homo sapiens
19.7 μg × h/mL	800 mg single, oral	AMPICILLIN serum	Homo sapiens
9.3 μg × h/mL	400 mg 4 times / day multiple, oral	AMPICILLIN serum	Homo sapiens
9 μg × h/mL	400 mg 4 times / day multiple, oral	AMPICILLIN serum	Homo sapiens
9.6 μg × h/mL	400 mg single, oral	AMPICILLIN serum	Homo sapiens
7.4 μg × h/mL	400 mg single, oral	AMPICILLIN serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
0.9 h	800 mg single, oral	AMPICILLIN serum	Homo sapiens
0.61 h	400 mg single, oral	AMPICILLIN serum	Homo sapiens
0.83 h	800 mg single, oral	AMPICILLIN serum	Homo sapiens
0.67 h	400 mg 4 times / day multiple, oral	AMPICILLIN serum	Homo sapiens
0.7 h	400 mg 4 times / day multiple, oral	AMPICILLIN serum	Homo sapiens
0.68 h	400 mg single, oral	AMPICILLIN serum	Homo sapiens
0.85 h	400 mg single, oral	AMPICILLIN serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
70%			LENAMPICILLIN serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1000 mg 4 times / day multiple, oral Highest studied dose	unhealthy, ADULT	Other AEs: Diarrhea, Eruption...
3000 mg single, oral Highest studied dose	unhealthy, ADULT

Showing 1 to 2 of 2 entries

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AEs

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AE	Significance	Dose	Population
Eruption	grade 1, 1%	1000 mg 4 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Diarrhea	grade 1-2, 2%	1000 mg 4 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Hoarseness	grade 2, 1%	1000 mg 4 times / day multiple, oral Highest studied dose	unhealthy, ADULT

Showing 1 to 3 of 3 entries

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PubMed

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Title	Date	PubMed
[Clinical studies on lenampicillin in the therapy of skin and soft tissue infections].	1985 Jun	4046172
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

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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
Record UNII	8M568DM08K
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Classification Tree

Code System

Code

Beta-Lactam Antibiotic

NCI_THESAURUS

C1500

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Code System

Code

Type

Description

INN

5467

PRIMARY

CAS

86273-18-9

PRIMARY

EPA CompTox

DTXSID1057901

PRIMARY

ChEMBL

CHEMBL2106329

PRIMARY

PUBCHEM

65646

PRIMARY

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Related Record

Type

Details


					6U90E2WB40

LENAMPICILLIN HYDROCHLORIDE

SALT/SOLVATE -> PARENT

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Related Record

Type

Details


					8M568DM08K

LENAMPICILLIN

ACTIVE MOIETY

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.ncbi.nlm.nih.gov/pubmed/4053214">https://www.ncbi.nlm.nih.gov/pubmed/4053214</a></span></span></div></div>

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

Description

C_max

T_1/2

F_unbound