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			{{Short description|Antibiotic medication}}
	{{Drugbox
			{{Infobox drug
⚫	| verifiedrevid = 408381026
			| Verifiedfields = changed
		⚫	| verifiedrevid = 448213645
	<!--Combo data-->		<!--Combo data-->
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	<!--Clinical data-->		<!--Clinical data-->
			| synonyms = penicillin G procaine, procaine penicillin G, procaine penicillin
	| tradename =
			| tradename = Bicillin C-R,<ref name=Ric2015/> other
	| Drugs.com = {{drugs.com|monograph|novocain}}		| Drugs.com = {{drugs.com|pro|penicillin-g-procaine}}
	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->		| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	| pregnancy_US = <!-- A / B / C / D / X -->		| pregnancy_US = B
			| pregnancy_US_comment = <ref name=Ric2015/>
	| pregnancy_category =		| pregnancy_category =
	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->		| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->		| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->		| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
	| legal_US = Rx-only		| legal_US = Rx-only
	| legal_status =		| legal_status =
	| routes_of_administration =		| routes_of_administration = IM
	<!--Identifiers-->		<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 54-35-3		| CAS_number = 54-35-3
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 1LW5K9CIR1
	| ATC_prefix = J01		| ATC_prefix = J01
	| ATC_suffix = CE09		| ATC_suffix = CE09
	| ATC_supplemental = {{ATCvet|J51|CE09}}		| ATC_supplemental = {{ATCvet|J51|CE09}}
	| PubChem =		| PubChem =
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1628385
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank =		| DrugBank =
	<!--Chemical data-->		<!--Chemical data-->
	}}		}}
			<!-- Definition and medical uses -->
			'''Procaine benzylpenicillin''' also known as '''penicillin G procaine''', is an ] useful for the treatment of a number of ].<ref name=WHO2008/> Specifically it is used for ], ], ], ], ], ], and ].<ref name=WHO2008/> It is given by ].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free | pages=113, 607, 618 }}</ref>
			<!-- Side effects and mechanism -->
	'''Procaine benzylpenicillin''' (]), also known as '''procaine penicillin''', is a form of ] which is a combination of ] and the ] agent ]. Following deep ] injection, it is slowly absorbed into the circulation and ] to benzylpenicillin — thus it is used where prolonged low concentrations of benzylpenicillin are required.
			Side effects include pain at the site of injection, ], ], and ]s including ].<ref name=WHO2008/> When used to treat syphilis a reaction known as ] may occur.<ref name=WHO2008/> It is not recommended in those with a history of ] or ] allergy.<ref name=Ric2015>{{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=95}}</ref><ref name=WHO2008/> Use during ] and ] is relatively safe.<ref name=Ric2015/><ref name=WHO2008/> Procaine benzylpenicillin is in the ] and ] family of medications.<ref name=WHO2008/> It works via ] and results in bacterial death.<ref name=WHO2008/><ref name=FDA2016>{{cite web|title=Penicillin G Procaine - FDA prescribing information, side effects and uses|url=https://www.drugs.com/pro/penicillin-g-procaine.html|website=www.drugs.com|access-date=10 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220230645/https://www.drugs.com/pro/penicillin-g-procaine.html|archive-date=20 December 2016}}</ref> Procaine makes the combination long acting.<ref>{{cite book|last1=Ebadi|first1=Manuchair|title=Desk Reference of Clinical Pharmacology, Second Edition|date=2007|publisher=CRC Press|isbn=9781420047448|page=555|url=https://books.google.com/books?id=ihxyHbnj3qYC&pg=PA555|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220152414/https://books.google.ca/books?id=ihxyHbnj3qYC&pg=PA555|archive-date=2016-12-20}}</ref>
			<!-- Society and culture -->
	This combination is aimed at reducing the pain and discomfort associated with a large ] of penicillin. It is widely used in veterinary settings.
			Procaine benzylpenicillin was introduced for medical use in 1948.<ref name=FDA2016/> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref>
	==Uses==		==Medical uses==
	Specific indications for procaine penicillin include:<ref name="AMH2006">{{cite book | editor=Rossi S, editor | title=] | year=2006 | location=Adelaide | publisher=Australian Medicines Handbook | isbn=0-9757919-2-3}}</ref>		Specific indications for procaine penicillin include:<ref name="AMH2006">{{cite book | editor=Rossi S | title=] | year=2006 | location=Adelaide | publisher=Australian Medicines Handbook | isbn=0-9757919-2-3}}</ref>
	*]		* ]
	**In the United States, '''Bicillin C-R''' (a injectable suspension which 1.2 million units of ] & 1.2 million units of procaine penicillin per 4 mL) is not recommended for treating syphilis, since it contains only half the recommended dose of benzathine penicillin. Medication errors have been made due to the confusion between '''Bicillin L-A''' & '''Bicillin C-R'''.<ref>{{cite journal |author= |title=Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004 |journal=MMWR Morb. Mortal. Wkly. Rep. |volume=54 |issue=9 |pages=217–9 |year=2005 |pmid=15758893 |doi= |author1= Centers for Disease Control and Prevention (CDC)}}</ref> As a result, changes in product packaging have been made; specifically, the statement "Not for the Treatment of Syphilis" has been added in red text to both the Bicillin CR and Billin CR 900/300 syringe labels.<ref>United States Food & Drug Administration. Published December 1, 2004. Last accessed June 18, 2007.</ref>		** In the United States, Bicillin C-R (an injectable suspension which 1.2 million units of ] and 1.2 million units of procaine penicillin per 4 ml) is not recommended for treating syphilis, since it contains only half the recommended dose of benzathine penicillin. Medication errors have been made due to the confusion between Bicillin L-A & Bicillin C-R.<ref>{{cite journal |title=Inadvertent use of Bicillin C-R to treat syphilis infection—Los Angeles, California, 1999–2004 |journal=MMWR Morb. Mortal. Wkly. Rep. |volume=54 |issue=9 |pages=217–9 |year=2005 |pmid=15758893 |author1= Centers for Disease Control and Prevention (CDC)|pmc=6820132 }}</ref> As a result, changes in product packaging have been made; specifically, the statement "Not for the Treatment of Syphilis" has been added in red text to both the Bicillin CR and Billin CR 900/300 syringe labels.<ref>United States Food & Drug Administration. {{webarchive|url=https://web.archive.org/web/20090114183518/https://www.fda.gov/bbs/topics/ANSWERS/2004/ANS01329.html |date=2009-01-14 }} Published December 1, 2004. Last accessed June 18, 2007.</ref>
	*] infections where compliance with oral treatment is unlikely		* ] infections where compliance with oral treatment is unlikely
	*Alongside Pen V and Erythromycin, Bicillin C-R is used to treat], given as one IM injection		* Alongside Pen V and Erythromycin, Bicillin C-R is used to treat ], given as one IM injection
	*], ]		* ], ]
	*Procaine penicillin is also used as an adjunct in the treatment of ].		* Procaine penicillin is also used as an adjunct in the treatment of ].
			== Adverse effects ==
			{{further|Penicillin drug reaction}}
			At high doses procaine penicillin can cause seizures and CNS abnormalities due to procaine present in it.{{citation needed|date=March 2023}}
			==Mechanism==
			It is a form of ] which is a salt of ] and the ] agent ].<ref>{{cite book|title=Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Fiftieth Meeting of the Joint FAO/WHO Expert Committee on Food Additives : Rome, 17-26 February 1998|date=1999|publisher=Food & Agriculture Org.|isbn=9789251042809|page=|url=https://archive.org/details/bub_gb_jMCHWPfDYf4C|language=en}}</ref> The salt has weak solubility, and is prepared as a suspension. Upon injection it forms a deposit within tissue (a "]'), and the salt slowly dissolves into ] - ] the two molecules into their bioactive forms over an extended period. Procaine acts as a local anaesthetic to reduce the discomfort of the depot, while benzylpenicillin enters into circulation and binds to bacterial cell walls, inhibiting their upkeep and production. This eventually leads to cell ] (bursting). The term "hydrolyzed" is incorrectly used in some medical literature to describe the dissociation of the salt and resulting benzylpenicillin, but this is inaccurate - the molecules themselves are unchanged and no water is consumed in the reaction. The products are the two oppositely charged bioactive molecules.<ref>{{Cite web |last=PubChem |title=Penicillin G Procaine |url=https://pubchem.ncbi.nlm.nih.gov/compound/Penicillin-G-Procaine |access-date=2025-01-13 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite journal |last=Tobin |first=T. |last2=Tai |first2=C. Y. |last3=O'Leary |first3=J. |last4=Sturma |first4=L. |last5=Arnett |first5=S. |date=April 1977 |title=Pharmacology of procaine in the horse: evidence against the existence of a "procaine - penicillin" complex |url=https://pubmed.ncbi.nlm.nih.gov/851276/ |journal=American Journal of Veterinary Research |volume=38 |issue=4 |pages=437–442 |issn=0002-9645 |pmid=851276}}</ref>
	== Compendial status ==		== Compendial status ==
			* ]<ref name=ibp2009>{{cite web| last =British Pharmacopoeia Commission Secretariat| title =Index (BP 2009)| url =http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf| access-date =26 March 2010| url-status =dead| archive-url =https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf| archive-date =11 April 2009}}</ref>
	* ] <ref name=ibp2009>{{cite web
	| last = British Pharmacopoeia Commission Secretariat
			==See also==
	| first =
			* ]
	| authorlink =
	| coauthors =
	| title = Index (BP 2009)
	| work =
	| publisher =
	| date =
	| url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
	| doi =
	| accessdate = 26 March 2010
	}}</ref>
	==References==		==References==
	{{reflist}}		{{reflist}}
	== See also ==		== External links ==
			* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/procaine%20benzylpenicillin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Penicillin G Procaine }}
	* ]
	{{PenicillinAntiBiotics}}		{{PenicillinAntiBiotics}}
			{{portal bar|Medicine}}
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