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MedKoo Cat#: 561615 | Name: Lenampicillin HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lenampicillin is a prodrug of ampicillin, developed to improve oral bioavailability. Upon administration, it is rapidly hydrolyzed to active ampicillin, which exhibits broad-spectrum antibacterial activity against both Gram-positive and some Gram-negative bacteria. The antibacterial spectrum includes Streptococcus pneumoniae, Staphylococcus aureus (non-β-lactamase-producing strains), Escherichia coli, Haemophilus influenzae, and Proteus mirabilis. Minimum inhibitory concentration (MIC) values of the released ampicillin typically range from 0.25 to 8 µg/mL, depending on the organism. Lenampicillin itself has limited direct antimicrobial activity until metabolized, and its clinical efficacy mirrors that of ampicillin, with peak plasma concentrations of free ampicillin reaching approximately 4–6 µg/mL within 1–2 hours post-oral dose (250–500 mg), supporting its use in respiratory, urinary, and gastrointestinal tract infections.

Chemical Structure

Lenampicillin HCl
Lenampicillin HCl
CAS#80734-02-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 561615

Name: Lenampicillin HCl

CAS#: 80734-02-7 (HCl)

Chemical Formula: C21H24ClN3O7S

Exact Mass: 0.0000

Molecular Weight: 497.95

Elemental Analysis: C, 50.65; H, 4.86; Cl, 7.12; N, 8.44; O, 22.49; S, 6.44

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Related CAS #
80734-02-7 (HCl) 86273-18-9 (free)
Synonym
Lenampicillin HCl; Lenampicillin Hydrochloride; Takacillin; Lenampicilline Hydrochloride; KBT-1585; KBT 1585; KBT1585;
IUPAC/Chemical Name
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Hydrochloride
InChi Key
FXXSETTYJSGMCR-GLCLSGQWSA-N
InChi Code
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
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC([C@H](N)C3=CC=CC=C3)=O)N1C2=O)OCC4=C(C)OC(O4)=O.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lenampicillin hydrochloride (KBT 1585 hydrochloride) is an orally active prodrug of Ampicillin and is an effective beta-lactam antibacterial agent that inhibits bacterial penicillin-binding proteins (transpeptidase).
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 100.0 200.82
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 497.95 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
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