Physical and Chemical Structure of Penamecillin - Essay Example

Physical and Chemical Structure of Penamecillin NamesAdditional names for penamecillin include penamecilline, penamecillinum, penamecillina, penamecillinum, penamecillina, and acetoxymethyl benzylpenicillinate (PubChem, ch 1). Other chemical and pharmacological text refer to it as penamecilina, penamecillin, or otherwise 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-(2s-(2alpha,5alpha,6beta), or benzylpenicillin acetoxymethyl ester. Penamecillin IUPAC name is acetyloxymethyl 3, 3-dimethyl-7-oxo-6-[(2-phenylacetyl) amino]-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylate (PubMed, ch 1).

CAS name for penamecillin is (2s, 5r, 6r)-3, hydroxymethyl (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate , 3-dimethyl-7-oxo-6-[(phenylacetyl) amino]-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid (acetyloxy) methyl ester. Furthermore, the CAS registry number for penamecillin is 983-85-7, and the compound InChIKey, is NLOOMWLTUVBWAW-UHFFFAOYSA-N (PubMed, ch 1). Source: (PubChem)Physical and Chemical Structure Penamecillin has a molecular weight of 406.

45278 g/mol with a molecular formula of C19H22N2O6. It is a monoclinic crystalline compound (PubChem, ch 4). The compound has a density of 1.376g/cm3, a boiling point of 648.774°c at 760 mmhg, with a melting point range of 105.5 °c to 111 °c, and a refractive index of 1.609 (Gibaldi And Schwartz, 362 ). It is moderately soluble in water but insoluble in petroleum ether. However, penamecillin is very soluble in methanol, ethanol, ethyl acetate, and benzene. It is also readily soluble in dimethylsulfoxide, chloroform, acetone, trichloromethaneand ether.

Furthermore, it is an unstructured crystalline white powder with precise optical rotation of +269 deg, at 20 deg C/D methanol. It also possesses a flash point of 346.2°C, with an inflammable limit of 364°C when it is a settled powder, and 442°C when it is in form of spun powder. Furthermore, it has a slight characteristic odour, and its decomposition temperature is > 105 °C. In terms of stability and reactivity, penamecillin is stable within ambient temperatures, and should be kept away from heat or ignition sources.

It is also a readily biodegradable compound even though it is not a bioaccumulation or eco-toxicity compound (PubChem, ch 4).The computed physical and chemical properties includesH-bond donor1H-bond acceptor7Rotatable bond count8Tautomer count4Exact mass406.119857Monoisotopic mass406.119857Topological polar surface area127Heavy atom count28Formal charge0Complexity661Isotope atom countSource: (PubChem)0Defined atom stereocenter count0Undefined atom stereocenter count3Defined bond stereocenter count0Undefined bond stereocenter count0Covalently-bonded unit count1Feature 3d acceptor count4Feature 3d donor count1Feature 3d hydrophobe count1Feature 3d ring count3Effective rotor count9.

8Conformer sampling rmsd1.2Specific gravity 400 - 550 kg/m3Source: (Pubchem, ch 5) Discovery and Synthesis Two scientists, Jansen and Russell managed to synthesis acetoxymethyl ester from the penicilins. They discovered that penamecillin was a result of absorption arising from enzymatic hydrolysis of non-specific esterases, into the hydroxymethyl. Accordingly, Penamecillin is an acetoxymethyl ester from benzylpenicillin, and is formed by rapid hydrolysis through the reaction of non-specific esterases (Randall and Arias, 96).

UsesIt is commonly used in chemotherapeutic function, as an antibacterial and antibiotic, since it significantly sustains blood levels (Gibaldi and Schwartz, 5). Currently, it is widely used as a pro-drug of benzylpenicillin as it enhances its bioavailability, in order to improve its absorption, distribution, and excretion. Penamecillin has a crucial pharmacological characteristic of inhibiting. However, overexposure in ultrasensitive persons leads to allergic reactions arising from urticaria leading to anaphylactic shock (Randall and Arias, 96)ToxicityIn terms of acute toxicity, Penamecillin is practically not that harmful via inhalation, swallowing, or in contact with skin, since it is a sensitizer.

But at high doses, it results in skin irritation as well as that of mucous membranes. Eye contact results in transitory irritation and thermal decomposition results in flammable plus toxic outcomes (PubChem, ch 5).Works CitedGibaldi, M And M A Schwartz. "The Pharmacokinetics Of Penamecillin." Br. J. Pharmac. Chemother 28.3 (1966): 360-366.PubChem. "Penamecillin - Compound Summary (CID 13795)." 2012. 15 November 2012 .Randall, Patricia S and Irwin M Arias. Concepts in biochemical pharmacology, Part 3.

Springer, 1975.