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

MedKoo CAT#: 317179

CAS#: 32887-01-7

Description: Mecillinam (INN) or amdinocillin (USAN) is an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has also been used to treat typhoid and paratyphoid fever. Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam. Neither drug is available in the United States.


Chemical Structure

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Amdinocillin
CAS# 32887-01-7

Theoretical Analysis

MedKoo Cat#: 317179
Name: Amdinocillin
CAS#: 32887-01-7
Chemical Formula: C15H23N3O3S
Exact Mass: 325.14601
Molecular Weight: 325.43
Elemental Analysis: C, 55.36; H, 7.12; N, 12.91; O, 14.75; S, 9.85

Size Price Shipping out time Quantity
100mg USD 240 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-07. Prices are subject to change without notice.

Amdinocillin purity > 95%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Synonym: Mecillinam; AMDINOCILLIN; Coactin; Penicillin HX; Mecillinamum; Hexacillin; FL 1060; FL-1060; FL1060

IUPAC/Chemical Name: (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

InChi Key: BWWVAEOLVKTZFQ-CXUHLZMHSA-N

InChi Code: InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/b16-9+

SMILES Code: CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)O)C

Appearance:
Solid powder

Purity:
>95% (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, not in water

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 325.43 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Thulin E, Sundqvist M, Andersson DI. Amdinocillin (Mecillinam) resistance mutations in clinical isolates and laboratory-selected mutants of Escherichia coli. Antimicrob Agents Chemother. 2015 Mar;59(3):1718-27. doi: 10.1128/AAC.04819-14. Epub 2015 Jan 12. PubMed PMID: 25583718; PubMed Central PMCID: PMC4325821.

2: Kerrn MB, Frimodt-Møller N, Espersen F. Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. PubMed PMID: 12604534; PubMed Central PMCID: PMC149286.

3: Olson ME, Nickel JC, Khoury AE, Morck DW, Cleeland R, Costerton JW. Amdinocillin treatment of catheter-associated bacteriuria in rabbits. J Infect Dis. 1989 Jun;159(6):1065-72. PubMed PMID: 2656876.

4: Yourassowsky E, van der Linden MP, Lismont MJ, Crokaert F, Glupczynski Y. Protective effect of amdinocillin against emergence of resistance to ceftazidime in Enterobacter cloacae. Antimicrob Agents Chemother. 1988 Nov;32(11):1632-5. PubMed PMID: 3075433; PubMed Central PMCID: PMC175942.

5: Bornemann LD, Castellano S, Lin AH, Enthoven D, Patel IH. Influence of food on bioavailability of amdinocillin pivoxil. Antimicrob Agents Chemother. 1988 Apr;32(4):592-4. PubMed PMID: 3377469; PubMed Central PMCID: PMC172228.

6: Nachamkin I, Gibson G, Sawyer K, Samel C, Skalina D. In vitro activity of amdinocillin in combination with other beta-lactam antibiotics against aminoglycoside-susceptible and resistant gram-negative bacteria. Diagn Microbiol Infect Dis. 1988 Feb;9(2):87-96. PubMed PMID: 3383549.

7: Eng RH, Liu R, Smith SM, Johnson ES, Cherubin CE. Amdinocillin: interaction with other beta-lactam antibiotics for gram-negative bacteria. Chemotherapy. 1988;34(1):18-26. PubMed PMID: 3258230.

8: Sanders CC, Sanders WE Jr, Goering RV, McCloskey RV. Leakage of beta-lactamase: a second mechanism for antibiotic potentiation by amdinocillin. Antimicrob Agents Chemother. 1987 Aug;31(8):1164-8. PubMed PMID: 3498436; PubMed Central PMCID: PMC174897.

9: Isenberg HD, Tilton RC, Barry AL, Beskid G, Cleeland R, Fallat V, Murray PR, Pierson C, Squires E. Collaborative clinical laboratory study of a broth-disk test for determination of bacterial susceptibility to beta-lactams in combination with amdinocillin. J Clin Microbiol. 1987 Jul;25(7):1195-200. Erratum in: J Clin Microbiol 1987 Oct;25(10):2036. PubMed PMID: 3611312; PubMed Central PMCID: PMC269175.

10: Whelton A, Spilman PS, Stout RL, Delgado FA. The influence of renal functional changes on the intrarenal distribution and urinary kinetics of amdinocillin. Ren Fail. 1987;10(2):101-6. PubMed PMID: 3685477.