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MedKoo Cat#: 592779 | Name: Amdinocillin pivoxil
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Description:

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

Amdinocillin pivoxil is a Pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.

Chemical Structure

Amdinocillin pivoxil
Amdinocillin pivoxil
CAS#32886-97-8 (pivoxil)

Theoretical Analysis

MedKoo Cat#: 592779

Name: Amdinocillin pivoxil

CAS#: 32886-97-8 (pivoxil)

Chemical Formula: C21H33N3O5S

Exact Mass: 439.2141

Molecular Weight: 439.57

Elemental Analysis: C, 57.38; H, 7.57; N, 9.56; O, 18.20; S, 7.29

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
32887-01-7 (free acid) 75027-15-5 (methylacetate) 32886-97-8 (pivoxil) 32887-03-9 (pivoxil HCl)
Synonym
Amdinocillin pivoxil, Pivmecillinam
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1H-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S-(2alpha,5alpha,6beta))-
InChi Key
NPGNOVNWUSPMDP-UTEPHESZSA-N
InChi Code
InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/b22-12+/t14-,15+,17-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2/N=C/N3CCCCCC3)N1C2=O)OCOC(C(C)(C)C)=O
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 439.57 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: Bader MS, Loeb M, Leto D, Brooks AA. Treatment of urinary tract infections in the era of antimicrobial resistance and new antimicrobial agents. Postgrad Med. 2020 Apr;132(3):234-250. doi: 10.1080/00325481.2019.1680052. Epub 2019 Oct 24. PMID: 31608743. 2: Nicolle LE. Pivmecillinam in the treatment of urinary tract infections. J Antimicrob Chemother. 2000 Sep;46 Suppl 1:35-9; discussion 63-5. Erratum in: J Antimicrob Chemother. 2008 Jul;62(1):215. PMID: 11051622. 3: Graninger W. Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. doi: 10.1016/s0924-8579(03)00235-8. PMID: 14527775. 4: Bleidorn J. Pivmecillinam is more effective than ibuprofen in symptom resolution in women with uncomplicated urinary tract infection: antibiotic treatment for UTI is important. BMJ Evid Based Med. 2019 Oct;24(5):e2. doi: 10.1136/bmjebm-2018-111084. Epub 2018 Dec 5. PMID: 30518669. 5: Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. PMID: 214285. 6: Nicolle LE. Pivmecillinam for the treatment of acute uncomplicated urinary infection. Int J Clin Pract. 1999 Dec;53(8):612-7. PMID: 10692756. 7: Parsons RL, Hossack GA, Paddock GM. Pharmacokinetics of pivmecillinam. Br J Clin Pharmacol. 1977 Jun;4(3):267-73. doi: 10.1111/j.1365-2125.1977.tb00711.x. PMID: 197981; PMCID: PMC1429083. 8: Frimodt-Møller N, Simonsen GS, Larsen AR, Kahlmeter G. Pivmecillinam, the paradigm of an antibiotic with low resistance rates in Escherichia coli urine isolates despite high consumption. J Antimicrob Chemother. 2022 Dec 23;78(1):289-295. doi: 10.1093/jac/dkac396. PMID: 36441168. 9: Dewar S, Reed LC, Koerner RJ. Emerging clinical role of pivmecillinam in the treatment of urinary tract infection in the context of multidrug-resistant bacteria. J Antimicrob Chemother. 2014 Feb;69(2):303-8. doi: 10.1093/jac/dkt368. Epub 2013 Sep 25. PMID: 24068280. 10: Pinart M, Kranz J, Jensen K, Proctor T, Naber K, Kunath F, Wagenlehner F, Schmidt S. Optimal dosage and duration of pivmecillinam treatment for uncomplicated lower urinary tract infections: a systematic review and meta- analysis. Int J Infect Dis. 2017 May;58:96-109. doi: 10.1016/j.ijid.2017.03.012. Epub 2017 Mar 21. PMID: 28341436. 11: Kranz J, Schmidt S, Lebert C, Schneidewind L, Schmiemann G, Wagenlehner F. Uncomplicated Bacterial Community-Acquired Urinary Tract Infection in Adults. Dtsch Arztebl Int. 2017 Dec 15;114(50):866-873. doi: 10.3238/arztebl.2017.0866. PMID: 29271346; PMCID: PMC5763001. 12: Retracted: In vivo mecillinam resistance in Escherichia coli after pivmecillinam treatment of a urinary tract infection. Microbiologyopen. 2019 Jul;8(7):e00770. doi: 10.1002/mbo3.770. Epub 2019 Jan 6. PMID: 30614202; PMCID: PMC10243602. 13: Moussa M, Abou Chakra M, Dellis A, Moussa Y, Papatsoris A. Pharmacotherapeutic advances for recurrent urinary tract infections in women. Expert Opin Pharmacother. 2020 Nov;21(16):2011-2026. doi: 10.1080/14656566.2020.1795128. Epub 2020 Jul 27. PMID: 32717156. 14: Kranz J, Schmidt S, Lebert C, Schneidewind L, Mandraka F, Kunze M, Helbig S, Vahlensieck W, Naber K, Schmiemann G, Wagenlehner FM. The 2017 Update of the German Clinical Guideline on Epidemiology, Diagnostics, Therapy, Prevention, and Management of Uncomplicated Urinary Tract Infections in Adult Patients. Part II: Therapy and Prevention. Urol Int. 2018;100(3):271-278. doi: 10.1159/000487645. Epub 2018 Mar 14. PMID: 29539622. 15: Hansen BÅ, Grude N, Lindbæk M, Stenstad T. The efficacy of pivmecillinam in oral step-down treatment in hospitalised patients with E. coli bacteremic urinary tract infection; a single-arm, uncontrolled treatment study. BMC Infect Dis. 2022 May 19;22(1):478. doi: 10.1186/s12879-022-07463-7. PMID: 35590284; PMCID: PMC9118732. 16: Sanderson P, Menday P. Pivmecillinam for bacteriuria in pregnancy. J Antimicrob Chemother. 1984 Apr;13(4):383-8. doi: 10.1093/jac/13.4.383. PMID: 6327600. 17: Sun LN, Zhao Y, Gao HY, Yang YL, Qian XP, Sun SY, Wang Y, Ding L, Wang YQ. LC-MS/MS methods for determination of unstable pivmecillinam and mecillinam in acidified human plasma: Application to a pharmacokinetic study. J Sep Sci. 2022 Jul;45(14):2543-2554. doi: 10.1002/jssc.202200070. Epub 2022 Jun 2. PMID: 35593582. 18: Freyhult E, Bremell D, Tängden T. Pivmecillinam – ett osäkert alternativ vid pyelonefrit. Lakartidningen. 2020 Aug 21;117:20048. Swedish. PMID: 32852775. 19: Jensen G. Pivmecillinam (Selexid) [Pivmecillinam (Selexid)]. Ugeskr Laeger. 1978 Apr 17;140(16):925-6. Danish. PMID: 206996. 20: Steurer J. Akuter, unkomplizierter Harnwegsinfekt: Pivmecillinam deutlich heilsamer als Ibuprofen. Praxis (Bern 1994). 2018 Sep;107(19):1055-1056. German. doi: 10.1024/1661-8157/a003067. PMID: 30227793.