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MedKoo Cat#: 598570 | Name: Lenampicillin

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
Lenampicillin
CAS#86273-18-9 (free)

Theoretical Analysis

MedKoo Cat#: 598570

Name: Lenampicillin

CAS#: 86273-18-9 (free)

Chemical Formula: C21H23N3O7S

Exact Mass: 461.1257

Molecular Weight: 461.48

Elemental Analysis: C, 54.66; H, 5.02; N, 9.11; O, 24.27; S, 6.95

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
80734-02-7 (HCl) 86273-18-9 (free)
Synonym
Lenampicillin; Lenampicilina;
IUPAC/Chemical Name
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
InChi Key
ZKUKMWMSYCIYRD-ZXFNITATSA-N
InChi Code
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
SMILES Code
O=c1oc(COC([C@H]2C(C)(C)S[C@H]3N2C([C@H]3NC([C@@H](c4ccccc4)N)=O)=O)=O)c(C)o1
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 461.48 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
1: Sum ZM, Sefton AM, Jepson AP, Williams JD. Comparative pharmacokinetic study between lenampicillin, bacampicillin and amoxycillin. J Antimicrob Chemother. 1989 Jun;23(6):861-8. PubMed PMID: 2759930. 2: Akimoto Y, Mochizuki Y, Uda A, Omata H, Shibutani J, Kaneko K, Yamane J, Fujii A, Yamamoto H. Ampicillin concentrations in human oral tissues following a single oral administration of lenampicillin. Gen Pharmacol. 1991;22(5):797-800. PubMed PMID: 1761182. 3: Marzo A, Monti N, Ripamonti M, Arrigoni Martelli E, Picari M. High-performance liquid chromatographic assay of ampicillin and its prodrug lenampicillin. J Chromatogr. 1990 May 16;507:235-9. PubMed PMID: 2380291. 4: Yoshii T, Hamamoto Y, Muraoka S, Furudoi S, Komori T. 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. J Infect Chemother. 2002 Mar;8(1):87-93. PubMed PMID: 11957126. 5: Akimoto Y, Mochizuki Y, Uda A, Omata H, Shibutani J, Nishimura H, Komiya M, Kaneko K, Kobayashi S, Kuboyama N, et al. Concentrations of ampicillin in human serum and mixed saliva following a single oral administration of lenampicillin, and relationship between serum and mixed saliva concentrations. J Nihon Univ Sch Dent. 1990 Mar;32(1):14-8. PubMed PMID: 2345375. 6: Saito A, Nakashima M. Pharmacokinetic study of lenampicillin (KBT-1585) in healthy volunteers. Antimicrob Agents Chemother. 1986 May;29(5):948-50. PubMed PMID: 3729355; PubMed Central PMCID: PMC284190. 7: Privitera G, Ortisi G, Scarpellini P, Nicastro G, Moro M, Cernuschi M. Impact of lenampicillin on the fecal flora of healthy volunteers. J Chemother. 1989 Jul;1(4 Suppl):600-2. PubMed PMID: 16312550. 8: Miki F, Soejima R. A review of clinical studies on lenampicillin in Japan. J Chemother. 1989 Jul;1(4 Suppl):640-2. PubMed PMID: 16312570. 9: Sefton AM, Jepson AP, Sun ZM, Williams JD. A comparative pharmacokinetic study between lenampicillin, bacampicillin and amoxycillin. J Chemother. 1989 Jul;1(4 Suppl):494-5. PubMed PMID: 16312500. 10: Motohiro T, Kawakami A, Aramaki M, Tanaka K, Koga T, Shimada Y, Tomita S, Sakata Y, Fujimoto T, Nishiyama T, et al. [Effect of orally administered lenampicillin and ampicillin on bacterial flora in human adult feces]. Jpn J Antibiot. 1986 Aug;39(8):2009-47. Japanese. PubMed PMID: 3795477. 11: Fujita K, Takahashi H, Takeshima M, Nonami E, Horie N, Kubota Y, Katsumata M, Kukita A, Watanabe S, Miura Y, et al. [Clinical studies on lenampicillin in the therapy of skin and soft tissue infections]. Jpn J Antibiot. 1985 Jun;38(6):1423-67. Japanese. PubMed PMID: 4046172. 12: Carlone NA, Tullio V, Cuffini AM. Bactericidal activity and morphological effects of lenampicillin on Staphylococcus aureus. J Chemother. 1989 Jul;1(4 Suppl):55-7. PubMed PMID: 16312302. 13: Awata N, Noumi K, Uemura Y, Takaki A, Aoyama T. [Metabolism of lenampicillin hydrochloride. II. Metabolism of promoiety]. Jpn J Antibiot. 1985 Jul;38(7):1785-93. Japanese. PubMed PMID: 4068221. 14: Mizuma T. Kinetic assessment of luminal degradation of orally effective prodrugs for rational drug development. J Pharm Sci. 2010 Feb;99(2):1078-86. doi: 10.1002/jps.21867. PubMed PMID: 19623605. 15: Fujita K, Takahashi H, Mizoguchi A, Takeshima M, Sasaki J, Nonami E, Harada S, Sato K, Hyang YS, Horie N, et al. [Clinical evaluation of lenampicillin in the treatment of superficial suppurative skin and soft tissue infection. A double-blind study comparing amoxicillin]. Jpn J Antibiot. 1985 Jul;38(7):1794-818. Japanese. PubMed PMID: 3906167. 16: Miki F, Ikuno Y, Inoue E, Yosiyama M, Murata T, Tanizawa S, Sakamoto K, Sakai H, Saito A, Tomizawa M, et al. [Comparative study of the effectiveness of lenampicillin and bacampicillin on bacterial pneumonia by double blind method]. Kansenshogaku Zasshi. 1985 Jun;59(6):605-38. Japanese. PubMed PMID: 3932547. 17: Sasaki J, Gotoh J, Morihana K, Sekiguchi T, Takai H, Ohmura H, Abe H, Ikejima K, Nishiyama K, Shiiki K, et al. [Clinical evaluation of lenampicillin in oral and maxillofacial infections]. Jpn J Antibiot. 1985 Jun;38(6):1468-508. Japanese. PubMed PMID: 4046173. 18: Guibert J, Kitzis MD, Yamabe S, Acar JF. Single- and multiple-dose pharmacokinetics of lenampicillin (KBT-1585) in healthy human subjects: comparative studies with amoxicillin. Chemioterapia. 1985 Aug;4(4):293-8. PubMed PMID: 4053214. 19: Awata N, Noumi K, Uemura Y, Takaki A, Aoyama T. [Metabolism of lenampicillin hydrochloride. I. Metabolism of ampicillin structure]. Jpn J Antibiot. 1985 Jul;38(7):1776-84. Japanese. PubMed PMID: 4068220. 20: Sasaki J, Gotoh J, Morihana K, Uematsu M, Takai H, Ohmura H, Abe H, Ikeshima K, Nishiyama K, Shiiki K, et al. [A comparative double blind study of lenampicillin and talampicillin in the treatment of oral infections]. Jpn J Antibiot. 1985 Sep;38(9):2453-80. Japanese. PubMed PMID: 3908737.