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

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
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

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