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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/10/22 15:06:48」(JST)
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Mepivacaine
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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 Y |
ATC code |
N01BB03 |
PubChem |
CID 4062 |
DrugBank |
DB00961 |
ChemSpider |
3922 Y |
UNII |
B6E06QE59J Y |
KEGG |
D08181 Y |
ChEBI |
CHEBI:6759 Y |
ChEMBL |
CHEMBL1087 Y |
Chemical data |
Formula |
C15H22N2O |
Mol. mass |
246.348 g/mol |
SMILES
- O=C(Nc1c(cccc1C)C)C2N(C)CCCC2
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InChI
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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) Y
Key:INWLQCZOYSRPNW-UHFFFAOYSA-N Y
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Y (what is this?) (verify)
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Mepivacaine // 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]
Anesthetics: Local anesthetics - primarily sodium channel blockers (N01B)
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Esters |
Esters of aminobenzoic acid
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- Amylocaine
- Benzocaine
- Butacaine
- Butamben
- Chloroprocaine
- Dimethocaine
- Meprylcaine
- Metabutethamine
- Metabutoxycaine
- Orthocaine
- Propoxycaine
- Procaine (Novocaine)
- Proxymetacaine
- Risocaine
- Tetracaine
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Esters of benzoic acid
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- 3-(p-Fluorobenzoyloxy)tropane
- Cocaine
- Cyclomethycaine
- Hexylcaine
- Piperocaine
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Amides |
- Articaine
- Bupivacaine # /Levobupivacaine/Ropivacaine
- Butanilicaine
- Carticaine
- Dibucaine
- Etidocaine
- Lidocaine #
- Mepivacaine
- Prilocaine
- Trimecaine
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Combinations |
Anesthetic/anesthetic - Lidocaine/prilocaine
Anesthetic/vasoconstrictor - Iontocaine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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anat (h/r/t/c/b/l/s/a)/phys (r)/devp/prot/nttr/nttm/ntrp
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noco/auto/cong/tumr, sysi/epon, injr
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English Journal
- Effects of periodontal afferent inputs on corticomotor excitability in humans.
- Zhang Y1, Boudreau S, Wang M, Wang K, Sessle B, Arendt-Nielsen L, Svensson P.Author information 1Department of Anatomy & Physiology, School of Stomatology, The Fourth Military Medical University, Xi'an, China.AbstractThe aim of the present study was to determine in humans whether local anaesthesia (LA) or nociceptive stimulation of the periodontal ligaments affects the excitability of the face primary motor cortex (MI) related to the tongue and jaw muscles, as measured by transcranial magnetic stimulation (TMS). Twelve healthy volunteers (11 men, 1 woman, 25.3 +/- 4.2 years) participated in two 3-h sessions separated by 7 days. The LA carbocain or the nociceptive irritant capsaicin was randomly injected into the periodontal ligament of the lower right central incisor. In both sessions, TMS-motor evoked potential (MEP) stimulus-response curves and corticomotor maps were acquired for the tongue and masseter muscles before (baseline) and at 5, 30 and 60 min post-application of carbocain or capsaicin. Transcranial magnetic stimulation-MEP stimulus-response curves were also acquired at these time points for the first dorsal interosseous (FDI) as an internal control. Burning pain intensity and mechanical sensitivity ratings to a von Frey filament applied to the application site were recorded on an electronic visual analogue scale (VAS). All subjects reported a decreased mechanical sensitivity (anova: P = 0.004) in the LA session and a burning pain sensation (VAS peak pain: 6.4 +/- 1.0) in the capsaicin session. No significant changes in cortical excitability of the MI, as reflected by TMS-MEP stimulus-response curves or corticomotor maps for the tongue, masseter or FDI were found between baseline and post-injection for the LA (anovas: P > 0.22) or capsaicin (anovas: P > 0.16) sessions. These findings suggest that a transient loss or perturbation in periodontal afferent input to the brain from a single incisor is insufficient to cause changes in corticomotor excitability of the face MI, as measured by TMS in humans.
- Journal of oral rehabilitation.J Oral Rehabil.2010 Jan;37(1):39-47. doi: 10.1111/j.1365-2842.2009.02016.x. Epub 2009 Oct 30.
- The aim of the present study was to determine in humans whether local anaesthesia (LA) or nociceptive stimulation of the periodontal ligaments affects the excitability of the face primary motor cortex (MI) related to the tongue and jaw muscles, as measured by transcranial magnetic stimulation (TMS).
- PMID 19889035
- Transurethral resection of the prostate after intraprostatic injections of mepivacain epinephrine: a preliminary communication.
- Schelin S.Author information Urology Section, Department of Surgery, Kalmar County Hospital, Kalmar, Sweden. sonny.schelin@telia.comAbstractOBJECTIVE: Transurethral resection of the prostate (TURP) has been the gold standard for treatment of obstructive benign prostatic hyperplasia since the 1970s. Intraprostatic injections of mepivacain epinephrine (ME) (Carbocain-Adrenalin) before Core Therm (Prostalund feedback treatment) have been used to anaesthetize the gland and reduce the intraprostatic blood flow, thereby reducing discomfort, treatment time and energy consumption during transurethral microwave thermotherapy. As a result of this experience, use of this technique before TURP, to reduce perioperative bleeding and blood loss during TURP surgery, was investigated. This paper presents the author's first clinical experiences using the Schelin Catheter to add intraprostatic infiltrations of ME before TURP.
- Scandinavian journal of urology and nephrology.Scand J Urol Nephrol.2009;43(1):63-7. doi: 10.1080/00365590802465061.
- OBJECTIVE: Transurethral resection of the prostate (TURP) has been the gold standard for treatment of obstructive benign prostatic hyperplasia since the 1970s. Intraprostatic injections of mepivacain epinephrine (ME) (Carbocain-Adrenalin) before Core Therm (Prostalund feedback treatment) have been u
- PMID 19085323
- Effect of local anaesthetics on wound healing. An experimental study with special reference to carbocain. Acta Anaesth. Scandinav. 1957, 2, 87-99.
- Nilsson E, Wendeberg B.
- Acta anaesthesiologica Scandinavica.Acta Anaesthesiol Scand.2007 Sep;51(8):991-1003; discussion 1004.
- PMID 17697292
Japanese Journal
- 血液透析患者の糖尿病性神経障害に対する星状神経節ブロック(SGB)療法の効果
- 口腔内浸潤麻酔時転換性障害を思わせるような不快症状を呈した1例
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