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MedKoo Cat#: 592867 | Name: Pivampicillin

Description:

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

Pivampicillin is a pivalate ester analog of Ampicillin. It is used to treat chronic obstructive pulmonary disease (COPD) in children and young adults.

Chemical Structure

Pivampicillin
Pivampicillin
CAS#33817-20-8

Theoretical Analysis

MedKoo Cat#: 592867

Name: Pivampicillin

CAS#: 33817-20-8

Chemical Formula: C22H29N3O6S

Exact Mass: 463.1777

Molecular Weight: 463.55

Elemental Analysis: C, 57.00; H, 6.31; N, 9.07; O, 20.71; S, 6.92

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 #
No Data
Synonym
Pivampicillin
IUPAC/Chemical 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 Key
ZEMIJUDPLILVNQ-KRWWSPQJSA-N
InChi Code
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
SMILES Code
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
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 463.55 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: 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.