Procaine Benzylpenicillin

(BAN, rINNM)
Procaine Benzylpenicillin Chemical formula
Synonyms: Bensylpenicillinprokain; Bentsyylipenisilliiniprokaiini; Benzilpenicilinas prokainas; Benzilpenicillin-prokain; Benzylopenicylina prokainowa; Benzylpenicillin Novocaine; Benzylpénicilline Procaïne; Benzylpenicillinum procainum; Penicillin G Procaine; Procaína bencilpenicilina; Procaïne Benzylpénicilline; Procaine Penicillin G; Procaini Benzylpenicillinum; Procainum Benzylpenicillinum; Prokain Benzilpenisilin; Prokain Penisilin G; Prokain-benzylpenicilin. 2-(4-Aminobenzoyloxy)ethyldiethylammonium (6R)-6-(2phenylacetamido)penicillanate monohydrate.
Cyrillic synonym: Прокаин Бензилпенициллин.

💊 Chemical information

Chemical formula: C13H20N2O2,C16H18N2O4S,H2O = 588.7.
CAS — 54-35-3 (anhydrous procaine benzylpenicillin); 6130-64-9 (procaine benzylpenicillin monohydrate).
ATC — J01CE09.
ATC Vet — QJ01CE09; QJ51CE09.

Pharmacopoeias.

In Chin., Eur., Int., and US.

Ph. Eur. 6.2

(Benzylpenicillin, Procaine). A white or almost white, crystalline powder. Slightly soluble in water; sparingly soluble in alcohol. A 0.33% solution in water has a pH of 5.0 to 7.5. Store in airtight containers.

USP 31

(Penicillin G Procaine). White crystals or white, very fine, microcrystalline powder, odourless or practically odourless. Slightly soluble in water; soluble in alcohol and in chloroform. It is rapidly inactivated by acids, by alkali hydroxides, and by oxidising agents. pH of a saturated solution in water is between 5.0 and 7.5.

💊 Adverse Effects and Precautions

As for Benzylpenicillin. Procaine benzylpenicillin should not be given to patients known to be hypersensitive to either of its components. Procaine benzylpenicillin should not be injected intravascularly since ischaemic reactions may occur. Severe, usually transient, reactions with symptoms of severe anxiety and agitation, confusion, psychotic reactions including visual and auditory hallucinations, seizures, tachycardia and hypertension, cyanosis, and a sensation of impending death have occasionally been reported with procaine benzylpenicillin and may be due to accidental intravascular injection. Since similar reactions have also occurred with other depot penicillin preparations that do not contain procaine, its presence is unlikely to be the major cause of such reactions, but may be a contributory factor, especially after injection of high doses. These reactions have been termed nonallergic, pseudoallergic, pseudoanaphylactic, or Hoigné’s syndrome; the term ‘embolic-toxic reaction’ has also been proposed.

💊 Interactions

💊 Pharmacokinetics

When procaine benzylpenicillin is given by intramuscular injection, it forms a depot from which it is slowly released and hydrolysed to benzylpenicillin. Peak plasma concentrations are produced in 1 to 4 hours, and effective concentrations of benzylpenicillin are usually maintained for 12 to 24 hours. However, plasma concentrations are lower than those after an equivalent dose of benzylpenicillin potassium or sodium. Distribution into the CSF is reported to be poor.

💊 Uses and Administration

Procaine benzylpenicillin has the same antimicrobial action as benzylpenicillin to which it is hydrolysed gradually following deep intramuscular injection. This results in a prolonged effect, but because of the relatively low blood concentrations produced, its use should be restricted to infections caused by microorganisms that are highly sensitive to penicillin. Procaine benzylpenicillin should not be used as the sole treatment for severe acute infections, or when bacteraemia is present. Procaine benzylpenicillin is used mainly in the treatment of syphilis; other indications have included pneumonia. Procaine benzylpenicillin is given by deep intramuscular injection in usual doses of 0.6 to 1.2 g daily. Patients with syphilis are given procaine benzylpenicillin 1.2 g daily for 10 to 14 days; infants up to 2 years of age with congenital syphilis may be given 50 mg/kg daily. Treatment may be continued for 3 weeks in patients with late syphilis. Procaine benzylpenicillin is also used in combined preparations with other penicillins, including benzylpenicillin and benzathine benzylpenicillin.

💊 Preparations

USP 31: Penicillin G Benzathine and Penicillin G Procaine Injectable Suspension; Penicillin G Procaine for Injectable Suspension; Penicillin G Procaine Injectable Suspension.

Proprietary Preparations

Arg.: Mudapenil†; Penicil Dermol†; Austral.: Cilicaine Syringe; Cz.: Pendepon Compositum; Ger.: Jenacillin O†; Hung.: Retardillin; Mex.: Benzotripen; Farmabep; Promizol; Sodilin; Unicil 3/1; Unicil 6:3:3; NZ: Cilicaine; S.Afr.: Bio-Cillin; Novocillin†; Procillin; Spain: Aqucilina; Farmaproina; Turk.: Benzapen 6.3.3; Deposilin 6.3.3; Devapen; Iecilline; Penadur 6.3.3; Penkain-K; Procillin; USA: Crysticillin; Venez.: Pebencil†; Pronapen; Silcopen†. Multi-ingredient: Austria: Fortepen; Retarpen compositum; Braz.: Benapen; Benzapen G; Despacilina; Drenovac†; Expectovac†; Ginurovac†; Linfocilin†; Odontovac†; Ortocilin†; Pencil 400; Penkaron; Wycillin; Chile: Karbasalin†; Ger.: Bipensaar; Jenacillin A†; Retacillin compositum; Hong Kong: Penicillin G Procaine Fortified; Hung.: Promptcillin Forte; India: Bistrepen; Ital.: Tri-Wycillina†; Mex.: Bencelin Combinado; Benzanil Compuesto; Benzetacil Combinado; Hidrocilina; Lugaxil; Pecivax; Pendiben Compuesto; Penicil; Penipot; Penisodina; Penprocilina; Procilin; Respicil; Robencaxil; Suipen; Neth.: Penidural D/F†; Port.: Atralcilina; Lentocilin; Penadur 6.3.3†; Rus.: Bicillin-3 (Бициллин-3); Bicillin-5 (Бициллин-5); S.Afr.: Penilente Forte†; Ultracillin; Spain: Aqucilina D A; Benzetacil Compuesta; Cepacilina 633; USA: Bicillin C-R; Venez.: Benzetacil 3-3; Benzetacil 6-3-3.
Published May 08, 2019.