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Mepivacaine /mɛˈpɪvəkeɪn/ is a local anesthetic^[1] of the amide type. Mepivacaine has a reasonably rapid onset (more rapid than that of procaine) and medium duration of action (shorter than that of procaine) and is marketed under various trade names including Carbocaine and Polocaine.

Mepivacaine became available in the United States in the 1960s.

Mepivacaine is used in any infiltration and regional anesthesia.

It is supplied as the hydrochloride salt of the racemate.^[2]

Chemistry[edit]

Two primary methods of synthesis have been suggested. According to the first, mepivacaine is synthesized by reacting the ethyl ester of 1-methylpiperindine-2-carboxylic acid with 2,6-dimethylanilinomagnesium bromide, which is synthesized from 2,6-dimethylaniline and ethylmagnesium bromide.

E. Thuresson, H. Egner, U.S. Patent 2,799,679 (1957).
B.T. Ekenstam, B. von Egner, G. Petterson, Acta Chem. Scand., 11, 1183 (1957).
Rinderknecht, H. (1959). "Neue Lokalanästhetika". Helvetica Chimica Acta 42 (4): 1324–1327. doi:10.1002/hlca.19590420430. edit

According to the second method, reacting 2,6-dimethylaniline with the acid chloride of pyridine- carboxylic acid first gives the 2,6-xylidide of α-picolinic acid. Then the aromatic pyridine ring is reduced to piperidine by hydrogen in the presence of a platinum on carbon catalyst. The resulting 2,6-xylidide α-pipecolic acid is methylated to mepivacaine using formaldehyde with simultaneous reduction by hydrogen in the presence of platinum on carbon catalyst.

B.G. Petterson, U.S. Patent 4,110,331 (1977).

References[edit]

^ Porto GG, Vasconcelos BC, Gomes AC, Albert D (January 2007). "Evaluation of lidocaine and mepivacaine for inferior third molar surgery". Med Oral Patol Oral Cir Bucal 12 (1): E60–4. PMID 17195831.
^ Burm AG, Cohen IM, van Kleef JW, Vletter AA, Olieman W, Groen K (January 1997). "Pharmacokinetics of the enantiomers of mepivacaine after intravenous administration of the racemate in volunteers". Anesth. Analg. 84 (1): 85–9. doi:10.1097/00000539-199701000-00016. PMID 8989005.

External links[edit]

Mepivacaine at RxList

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UpToDate Contents

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1. 局所麻酔剤の浸潤 infiltration of local anesthetics
2. 局所麻酔剤に対するアレルギー反応 allergic reactions to local anesthetics
3. 末梢神経ブロックの概要 overview of peripheral nerve blocks
4. 頭皮裂傷の評価およびマネージメント assessment and management of scalp lacerations
5. 陰部神経ブロックおよび傍子宮頸管ブロック pudendal and paracervical block

English Journal

Effects of Mepivacaine 2% With Epinephrine in the Cardiovascular Activity of Patients Undergoing Third Molar Surgery: A Prospective Clinical Study.

Scarparo HC, Maia RN, de Gois SR, Costa FW, Ribeiro TR, Soares EC.SourceFrom the *Division of Oral Surgery, Department of Clinical Dentistry, School of Dentistry, Federal University of Ceará; †Division of Oral Surgery, Dr. José Frota Institute Hospital, Ceará; Divisions of ‡Oral Surgery, §Division of Oral Radiology, Department of Clinical Dentistry, Federal University of Ceará, Fortaleza-CE, ∥Department of Clinical Dentistry, Federal University of Ceará, Fortaleza-CE; and ¶Division of Stomatology and Oral Surgery, Department of Clinical Dentistry, School of Dentistry, Federal University of Ceará, Ceará, Brazil.
The Journal of craniofacial surgery.J Craniofac Surg.2013 Nov 22. [Epub ahead of print]
BACKGROUND: Cardiovascular effects of epinephrine, especially on blood pressure (BP) and heart rate (HR), have been well documented. When present in dental local anesthetic solutions, epinephrine concentration ranges from 5 to 20 µg/mL. Doses less than 200 µg are recommended to be clinically safe.
PMID 24275775

The role of electrical stimulation in ultrasound-guided subgluteal sciatic nerve block: a retrospective study on how response pattern and minimal evoked current affect the resultant blockade.

Hara K, Sakura S, Yokokawa N.SourceDepartment of Anesthesiology, University Hospital, Shimane University School of Medicine, Izumo, Japan.
Journal of anesthesia.J Anesth.2013 Nov 20. [Epub ahead of print]
PURPOSE: Nerve stimulation may be combined with ultrasound imaging for a block of deeply located nerves such as the sciatic nerve in the subgluteal region. At present, it is unknown how the use of nerve stimulation affects blockade after this nerve block. We retrospectively compared the effects of t
PMID 24253853

[Ultrasound-guided peripheral nerve block at wrist level for the treatment of idiopathic palmar hyperhidrosis with botulinum toxin.]

Olea E, Fondarella A, Sánchez C, Iriarte I, Almeida MV, Martínez de Salinas A.SourceServicio de Anestesiología y Reanimación, Hospital Universitario de Álava, Vitoria-Gasteiz, Álava, España. Electronic address: Erika.olea@osakidetza.net.
Revista espanola de anestesiologia y reanimacion.Rev Esp Anestesiol Reanim.2013 Nov 6. pii: S0034-9356(13)00229-6. doi: 10.1016/j.redar.2013.08.008. [Epub ahead of print]
OBJECTIVE: Evaluation of pain and degree of satisfaction in patients undergoing ultrasound-assisted peripheral regional block for the treatment of idiopathic palmar hyperhidrosis with botulinum toxin.PATIENTS AND METHODS: A descriptive, observational study of patients with palmar hyperhidrosis treat
PMID 24210213

Japanese Journal

斜角筋間腕神経叢ブロックによる肩関節鏡手術

杉原隆之
肩関節 35(2), 633-635, 2011
… Mepivacaine hydrochloride (1.5%) was used with an average of 23.6ml and ropivacaine hydrochloride hydrate (0.75%) was used with an average of 20.0ml. …
NAID 130001413768

膝蓋下脂肪体炎により下肢の痛みを生じていた1症例

山本洋介,山田信一,有川貴子,永田環,中川景子,大石羊子,澤田麻衣子,福重哲志,牛島一男
The journal of the Japan Society of Pain Clinicians = 日本ペインクリニック学会誌 17(4), 488-490, 2010-09-25
膝蓋下脂肪体炎で下肢痛を生じ，歩行困難となった症例を報告する．症例は 81歳の男性で，当科を受診する 1カ月半前に，右大腿前面から膝に及ぶ痛みが起こった． MRI検査により L3/4外側ヘルニアと判断され，仙骨硬膜外ブロックや L3の神経根ブロックを数回受けたが，痛みは軽減しなかった．膝の MRI検査で外側半月板変性も疑われ，膝関節内に局所麻酔薬の注入を受けたが，痛みは軽減せず，歩行困難となったの …
NAID 10027646205

Related Pictures

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★リンクテーブル★

リンク元	「メピバカイン」
拡張検索	「mepivacaine hydrochloride」

「メピバカイン」

Mepivacaine
Systematic (IUPAC) name
	(RS)-N-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide
Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a603026
Pregnancy cat.	C, use w/ caution, may cause fetal bradycardia
Legal status	?
Identifiers
CAS number	96-88-8
ATC code	N01BB03
PubChem	CID 4062
DrugBank	DB00961
ChemSpider	3922
UNII	B6E06QE59J
KEGG	D08181
ChEBI	CHEBI:6759
ChEMBL	CHEMBL1087
Chemical data
Formula	C15H22N2O
Mol. mass	246.348 g/mol
	SMILES O=C(Nc1c(cccc1C)C)C2N(C)CCCC2;
	InChI InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18) ; Key:INWLQCZOYSRPNW-UHFFFAOYSA-N ;
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