Bupivacaine

Structural formula
	1: 1 mixture of ( R ) -isomer (top) and ( S ) -isomer (bottom)
General
Non-proprietary name	Bupivacaine
other names	(±) -1-butyl- N - (2,6-dimethylphenyl) -2-piperidinecarboxamide ( IUPAC ); ( RS ) -1-butyl- N - (2,6-dimethylphenyl) -2-piperidinecarboxamide;
Molecular formula	C 18 H 28 N 2 O
External identifiers / databases
EC number	253-911-2
ECHA InfoCard	100.048.993
PubChem	2474
DrugBank	DB00297
Wikidata	Q422806
Drug information
ATC code	N01 BB01
Drug class	Local anesthetic
properties
Molar mass	288.43 g mol −1
Physical state	firmly
Melting point	107-108 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride monohydrate danger
H and P phrases	H: 300-310-330
	P: 260-264-280-284-301 + 310-302 + 350
Toxicological data	7.1 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bupivacaine is an amide-type local anesthetic introduced in 1963 . The drug is chiral and is used as a racemate . It has a relatively slow onset of action and a long duration of action of up to 12 hours.

application

Bupivacaine was introduced in 1963 and is used in anesthesia , mainly for anesthesia procedures near the spinal cord such as spinal or epidural anesthesia . Because of its relatively long duration of action, this substance is one of the most frequently used local anesthetics in general medicine. For local anesthesia in dentistry , it is not often employed, only in the context particularly prolonged treatments and therapeutic nerve blocks in pain.

unwanted effects

Bupivacaine has the highest toxicity of all local anesthetics , which can be particularly important in the event of unnoticed intravenous injection, but also in the event of increased absorption from the injection area. In particular, cardiac arrhythmias have been described which, in contrast to other local anesthetics, can occur before CNS side effects occur.

dosage

Experience to date has shown that a single dose of up to 150 mg bupivacaine hydrochloride is appropriate. Additional doses of up to 50 mg can then be given every two hours. A maximum dose of 2 mg / kg should not be exceeded within a period of four hours.

The recommendation of maximum doses for local anesthetics should be seen as an attempt to avoid excessive plasma levels by limiting the dose and thereby reducing the incidence of systemic toxic incidents. However, this concept has been the subject of heated discussions for some time, especially since maximum doses were more or less arbitrarily determined on the basis of data from (animal) experimental studies or historical case reports. However, since the plasma levels resulting after the injection of local anesthetics are influenced by a large number of pharmacokinetic, patient and blockade-specific factors, the real benefit of these recommendations from a toxicological point of view remains at least questionable. Incidents are observed, among other things, as a result of accidental intravascular injection.

Trade names

Monopreparations

Bucain (D, A), Carbostesin (D, A, CH), Dolanaest (D, A), Duracain (CH), Carbocaina (I), as well as generics (D, CH)

Combination preparations

Carbostesin (CH), generic (D)

Individual evidence

↑ External identifiers or database links for bupivacaine hydrochloride : CAS number: 18010-40-7, EC number: 241-917-8, ECHA InfoCard: 100.038.092 , PubChem : 64737 , ChemSpider : 58277 , Wikidata : Q27888209 .
↑ External identifiers or database links for bupivacaine hydrochloride monohydrate : CAS number: 73360-54-0, EC number: 642-205-3, ECHA InfoCard: 100.170.015 , PubChem : 5282419 , ChemSpider : 4445574 , DrugBank : DBSALT001512 , Wikidata : Q27887879 .
↑ ^a ^b Entry on bupivacaine. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.
↑ ^a ^b Data sheet Bupivacaine hydrochloride monohydrate from Sigma-Aldrich , accessed on May 31, 2018 ( PDF ).
↑ Michael Heck, Michael Fresenius: Repetitorium Anaesthesiologie. Preparation for the anesthesiological specialist examination and the European diploma in anesthesiology. 3rd, completely revised edition. Springer, Berlin / Heidelberg / New York et al. 2001, ISBN 3-540-67331-8 , p. 804.
^ Judith M. Jacob: Victory over pain . In: DENTAL MAGAZIN 6/2005, p. 50, accessed on July 3, 2016.
↑ Product information Bupivacain Accord 5 mg / ml solution for injection , accessed on February 15, 2019.
↑ W. Zink, BM Graf, Local Anesthetic Toxicity - Relevance of Recommended Maximum Doses? , Anästh Intensivmed, 2007, Issue 48, pp. 182–205, Aktiv Druck & Verlag GmbH, accessed on February 15, 2019.

[1] External identifiers or database links for bupivacaine hydrochloride : CAS number: 18010-40-7, EC number: 241-917-8, ECHA InfoCard: 100.038.092 , PubChem : 64737 , ChemSpider : 58277 , Wikidata : Q27888209 .

[2] External identifiers or database links for bupivacaine hydrochloride monohydrate : CAS number: 73360-54-0, EC number: 642-205-3, ECHA InfoCard: 100.170.015 , PubChem : 5282419 , ChemSpider : 4445574 , DrugBank : DBSALT001512 , Wikidata : Q27887879 .

[RÖMPP_Online-3] Entry on bupivacaine. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.

[Sigma-4] Data sheet Bupivacaine hydrochloride monohydrate from Sigma-Aldrich , accessed on May 31, 2018 ( PDF ).

[5] Michael Heck, Michael Fresenius: Repetitorium Anaesthesiologie. Preparation for the anesthesiological specialist examination and the European diploma in anesthesiology. 3rd, completely revised edition. Springer, Berlin / Heidelberg / New York et al. 2001, ISBN 3-540-67331-8 , p. 804.

[6] Judith M. Jacob: Victory over pain . In: DENTAL MAGAZIN 6/2005, p. 50, accessed on July 3, 2016.

[7] Product information Bupivacain Accord 5 mg / ml solution for injection , accessed on February 15, 2019.

[8] W. Zink, BM Graf, Local Anesthetic Toxicity - Relevance of Recommended Maximum Doses? , Anästh Intensivmed, 2007, Issue 48, pp. 182–205, Aktiv Druck & Verlag GmbH, accessed on February 15, 2019.