Synonym
Penamecillin; WY20,788; WY-20,788; WY 20,788
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-(2S-(2alpha,5alpha,6beta))-, (acetyloxy)methyl ester
InChi Key
NLOOMWLTUVBWAW-HLLBOEOZSA-N
InChi Code
InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(CC3=CC=CC=C3)=O)N1C2=O)OCOC(C)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
406.45
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.
| 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: Agersborg HP, Batchelor A, Cambridge GW, Rule AW. The pharmacology of penamecillin. Br J Pharmacol Chemother. 1966 Mar;26(3):649-55. doi: 10.1111/j.1476-5381.1966.tb01844.x. PMID: 4959939; PMCID: PMC1510697.
2: Gibaldi M, Schwartz MA. The pharmacokinetics of penamecillin. Br J Pharmacol Chemother. 1966 Dec;28(3):360-6. doi: 10.1111/j.1476-5381.1966.tb01904.x. PMID: 19108231; PMCID: PMC1510880.
3: Matuz M, Benko R, Doro P, Hajdu E, Soos G. Non-prescription antibiotic use in Hungary. Pharm World Sci. 2007 Dec;29(6):695-8. doi: 10.1007/s11096-007-9132-0. Epub 2007 May 25. PMID: 17530434.
4: Czeizel AE, Rockenbauer M, Olsen J. Use of antibiotics during pregnancy. Eur J Obstet Gynecol Reprod Biol. 1998 Oct;81(1):1-8. doi: 10.1016/s0301-2115(98)00138-9. PMID: 9846705.
5: Kovács I, Bálintné HM, Bálint J. Adatok a penamecillin stabilitásvizsgálatához [Studies on penamecillin stability]. Acta Pharm Hung. 1978 Mar;48(2):54-61. Hungarian. PMID: 654919.
6: Sahoo GC, Rani M, Ansari Y, Jha C, Rana S, Dikhit MR, Moharana KC, Kumar R, Das P. Structure, evolution and virtual screening of NDM-1 strain from Kolkata. Int J Bioinform Res Appl. 2014;10(3):235-63. doi: 10.1504/IJBRA.2014.060761. PMID: 24794069.
7: Wagner A, Flaig R, Dittrich B, Schmidt H, Koritsánszky T, Luger P. Charge density and experimental electrostatic potentials of two penicillin derivatives. Chemistry. 2004 Jun 21;10(12):2977-82. doi: 10.1002/chem.200305627. PMID: 15214080.
8: Ivády G, Baranyai P, Tuma L, Inkei J. Kliniko-pharmakologische Daten über die Wirksamkeit des oralen Penicillinpräparates Penamecillin [Clinico-pharmacologic data on the effectiveness of the oral penicillin Penamecillin]. Acta Paediatr Acad Sci Hung. 1972;13(3):215-9. German. PMID: 4486601.
9: Schmidt T, Kovács P, Ujj G, Tóth-Martinez B, Institóris L Jr, Hernádi F. A benzilpenicillin-benzamido-metilészter farmakológiai vizsgálata. II. A benzilpenicillin-benzamido-metilészter és a penamecillin (maripen) farmakokinetikai tulajdonságainak összehasonlítása [Pharmacological study of benzylpenicillin-benzamido-methylester. II. Comparison of the pharmacokinetic properties of benzylpenicillin-benzamido-methylester and penamecillin (Moripen)]. Acta Pharm Hung. 1985 Jul;55(4):221-8. Hungarian. PMID: 4050450.
10: Zöllnerné Ivan E. Penamecillin és fenoxi-metil-penicillin (v-penicillin-sav) meghatározása a Maripen és a Vegacillin készítményekben infravörös spektrumok alapján [Determination of penamecillin and phenoxymethylpenicillin (v-penicillic acid) based on the infrared spectra of Maripen and Vegacillin]. Acta Pharm Hung. 1981 Jan;51(1):38-42. Hungarian. PMID: 6791461.
