Pharmakon1600-01503102

Base Information

• Chemical Name: Pharmakon1600-01503102
• CAS No.: 37661-08-8
• Molecular Formula: C21H27 N3 O7 S . Cl H
• Molecular Weight: 501.988
• NSC Number: 758228
• Mol file: 37661-08-8.mol

Synonyms:SR-05000001824;SPECTRUM1503102;Pharmakon1600-01503102;CCG-39301;NSC758228;SR-05000001824-3

Chemical Property of Pharmakon1600-01503102

Chemical Property:

• Vapor Pressure: 1.39E-19mmHg at 25°C
• Melting Point: 171-176° (dec)
• Boiling Point: 695.4°C at 760 mmHg
• Flash Point: 374.3°C
• PSA: 162.56000
• LogP: 3.12690
• Solubility.: Soluble in water, freely soluble in ethanol (96 per cent), soluble in methylene chloride.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 501.1336491
• Heavy Atom Count: 33
• Complexity: 756

Purity/Quality:

99% ^*data from raw suppliers

Bacampicillin hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)OC(C)OC(=O)C1C(SC2N1C(=O)C2NC(=O)C(C3=CC=CC=C3)N)(C)C.Cl
• Isomeric SMILES: CCOC(=O)OC(C)OC(=O)C1C(SC2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C.Cl
• Uses: Bacampicillin is a penicillin class of antibiotic. Bacampicillin is a prodrug of ampicillin (A634300) with improved oral bioavailability.
• Therapeutic Function: Antibacterial
• Clinical Use: Bacampicillin hydrochloride (Spectrobid) is the hydrochloridesalt of the 1-ethoxycarbonyloxyethyl ester of ampicillin.It is a prodrug of ampicillin with no antibacterial activity.After oral absorption, bacampicillin is hydrolyzed rapidly byesterases in the plasma to form ampicillin.Oral absorption of bacampicillin is more rapid and completethan that of ampicillin and less affected by food.Plasma levels of ampicillin from oral bacampicillin exceedthose of oral ampicillin or amoxicillin for the first 2.5 hoursbut thereafter are the same as for ampicillin and amoxicillin.49 Effective plasma levels are sustained for 12 hours,allowing twice-a-day dosing.

Technology Process of Pharmakon1600-01503102

There total 3 articles about Pharmakon1600-01503102 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

1-ethoxycarbonyloxyethyl 6β-aminopenicillanate p-toluenesulfonate (50972-01-5) + 2-(R)-2-phenyl-2-aminoacetyl chloride hydrochloride (40966-78-7,5321-31-3) → bacampicillin hydrochloride (37661-08-8,95530-84-0,95530-85-1)

Guidance literature:

With ammonium bicarbonate; triethylamine; In dichloromethane; at 7 - 10 ℃; for 0.833333h;

DOI:10.1248/cpb.32.4316

Reference yield:

magnesium sulfate (7487-88-9) + ampicillin (69-53-4) + 1-ethoxycarbonyloxyethyl bromide (89766-09-6) → bacampicillin Hydrochloride (37661-08-8)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; In acetic acid butyl ester; water; ethyl acetate; acetone;

Reference yield:

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 1-ethoxycarbonyloxy-ethyl ester (96606-98-3) → bacampicillin hydrochloride (37661-08-8,95530-84-0,95530-85-1) + (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (1256-08-2,6490-08-0)

Guidance literature:

With water; at 35 ℃; Rate constant; degradation in various buffers (pH 7.00-9.00);

DOI:10.1248/cpb.33.1202

upstream raw materials:

1-ethoxycarbonyloxyethyl 6β-aminopenicillanate p-toluenesulfonate

2-(R)-2-phenyl-2-aminoacetyl chloride hydrochloride

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 1-ethoxycarbonyloxy-ethyl ester

magnesium sulfate

Downstream raw materials:

ampicillin

ampicillin

Refernces

• 1、 Fujiwara,Kawashima. "Stabilization of ampicillin analogs in aqueous solution. VI. Kinetic analysis of the stabilization mechanism of bacampicillin with benzaldehyde in aqueous solution". . p. 1202 - 1213. Retrieved 2007/10/02.