Pivampicillin

  • CAT Number: I034850
  • CAS Number: 33817-20-8
  • Molecular Formula: C22H29N3O6S
  • Molecular Weight: 463.549
  • Purity: 98%
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Pivampicillin (Cat.No:I034850) is a pivalate ester analog of Ampicillin. It is used to treat chronic obstructive pulmonary disease (COPD) in children and young adults.

Catalog Number I034850
CAS Number 33817-20-8
Molecular Formula

C22H29N3O6S

Purity 98
Solubility Soluble in DMSO
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S-(2alpha,5alpha,6beta(S*)))-
InChI InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13?,14-,15+,18-/m1/s1
InChIKey ZEMIJUDPLILVNQ-KRWWSPQJSA-N
SMILES O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C(N)C3=CC=CC=C3)=O)N1C2=O)OCOC(C(C)(C)C)=O
Reference

1: Winther L, Baptiste KE, Friis C. Pharmacokinetics in pulmonary epithelial lining fluid and plasma of ampicillin and pivampicillin administered to horses. Res Vet Sci. 2012 Feb;92(1):111-5. doi: 10.1016/j.rvsc.2010.11.001. Epub 2010 Dec 7. PubMed PMID: 21144541.
2: Johansen HK, Børch K, Espersen F, Koch C, Høiby N. Randomised trial of pivampicillin plus pivmecillinam vs. pivampicillin in children and young adults with chronic obstructive pulmonary disease and infection with Haemophilus influenzae. Curr Med Res Opin. 1999;15(4):300-9. PubMed PMID: 10640263.
3: Bukh N. Double-blind comparison of pivmecillinam plus pivampicillin (‘Miraxid’) with pivampicillin alone in chronic bronchitis: a Danish multi-centre study. Pharmatherapeutica. 1983;3(6):422-8. PubMed PMID: 6312461.
4: Hey H, Matzen P, Andersen JT, Didriksen E, Nielsen B. A gastroscopic and pharmacological study of the disintegration time and absorption of pivampicillin capsules and tablets. Br J Clin Pharmacol. 1979 Sep;8(3):237-42. PubMed PMID: 497090; PubMed Central PMCID: PMC1429802.
5: Ensink JM, Moi A, Vulto AG, Tukker JJ. Bioavailability of pivampicillin and ampicillin trihydrate administered as an oral paste in horses. Vet Q. 1996;18 Suppl 2:S117-20. PubMed PMID: 8933688.
6: Ensink JM, Barneveld A, Klein WR, van Miert AS, Vulto AG. Oral bioavailability of pivampicillin in foals at different ages. Vet Q. 1994 May;16 Suppl 2:S113-6. PubMed PMID: 7801502.
7: Hjort N, Renmarker K, Rosberg B, Skog PA, Hey H. Tolerance of two ampicillin esters: a comparison of pivampicillin and bacampicillin. Pharmatherapeutica. 1983;3(6):398-404. PubMed PMID: 6353431.
8: Eriksson S, Zbornik J, Dahnsjö H, Erlanson P, Kahlmeter O, Fritz H, Bauer CA. The combination of pivampicillin and pivmecillinam versus pivampicillin alone in the treatment of acute pyelonephritis. Scand J Infect Dis. 1986;18(5):431-8. PubMed PMID: 3535049.
9: Eriksson M, Bolme P. The oral absorption of ampicillin, pivampicillin and amoxycillin in infants and children. Acta Pharmacol Toxicol (Copenh). 1981 Jul;49(1):38-42. PubMed PMID: 7336963.
10: Dewan J, Malik SK, Jindal SK, Sharma PL. A comparative randomized double-blind clinical trial of pivampicillin and ampicillin in lower respiratory tract infections. Int J Clin Pharmacol Ther Toxicol. 1982 Feb;20(2):85-7. PubMed PMID: 7037662.
11: Kvile G, Langeland P, Norling B. Treatment of salpingitis with pivampicillin. A comparison of twice-daily and thrice-daily dosages. Infection. 1980;8(1):32-6. PubMed PMID: 7372355.
12: Ensink JM, Klein WR, Mevius DJ, Klarenbeek A, Vulto AG. Bioavailability of oral penicillins in the horse: a comparison of pivampicillin and amoxicillin. J Vet Pharmacol Ther. 1992 Sep;15(3):221-30. PubMed PMID: 1433484.
13: Larsen H, Nielsen GL, Sørensen HT, Møller M, Olsen J, Schønheyder HC. A follow-up study of birth outcome in users of pivampicillin during pregnancy. Acta Obstet Gynecol Scand. 2000 May;79(5):379-83. PubMed PMID: 10830765.
14: Frimodt-Møller C, Vejlsgaard R. Pivmecillinam plus pivampicillin in complicated urinary tract infection. Double-blind comparison of the combination pivmecillinam/pivampicillin and pivmecillinam alone in patients with urinary tract infection. J Int Med Res. 1981;9(4):283-7. PubMed PMID: 6266897.
15: Holmquist B, Lundgren R. Pivmecillinam plus pivampicillin versus co-trimoxazole in patients undergoing transurethral prostate resection. Pharmatherapeutica. 1984;3(10):686-91. PubMed PMID: 6087368.
16: Svenungsson B, Ekwall E, Hansson HB. Efficacy of the combination pivampicillin/pivmecillinam compared to placebo in the treatment of convalescent carriers of nontyphi Salmonella. Infection. 1990 May-Jun;18(3):163-5. PubMed PMID: 2194971.
17: Christensen CH, Hartmann E. Treatment of sinusitis and otitis media with pivampicillin. Pharmatherapeutica. 1980;2(7):469-74. PubMed PMID: 7208541.
18: Cramers M, Kaspersen P, From E, Møller BR. Pivampicillin compared with erythromycin for treating women with genital Chlamydia trachomatis infection. Genitourin Med. 1988 Aug;64(4):247-8. PubMed PMID: 3169754; PubMed Central PMCID: PMC1194226.
19: Ensink JM, Vulto AG, van Miert AS, Tukker JJ, Winkel MB, Fluitman MA. Oral bioavailability and in vitro stability of pivampicillin, bacampicillin, talampicillin, and ampicillin in horses. Am J Vet Res. 1996 Jul;57(7):1021-4. PubMed PMID: 8807014.
20: Atkins MJ, Talbot DJ. A comparison of pivmecillinam/pivampicillin and amoxycillin in acute exacerbations of chronic bronchitis. J Int Med Res. 1987 Mar-Apr;15(2):115-20. PubMed PMID: 3556261.

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