Levobupivacaine free base
new
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319941

CAS#: 27262-47-1 (free base)

Description: Levobupivacaine is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by Abbott under the trade name Chirocaine. Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 percent less potent (by molarity) than racemic bupivacaine and has a longer motor block onset time.


Price and Availability

Size
Price

500mg
USD 150
10g
USD 850
Size
Price

1g
USD 250
100g
USD 2950
Size
Price

5g
USD 550
500g
USD 5450

Levobupivacaine free base, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 319941
Name: Levobupivacaine free base
CAS#: 27262-47-1 (free base)
Chemical Formula: C18H28N2O
Exact Mass: 288.2202
Molecular Weight: 288.435
Elemental Analysis: C, 74.96; H, 9.79; N, 9.71; O, 5.55


Related CAS #: 27262-47-1 (free base)   27262-48-2 (HCl)    

Synonym: Levobupivacaine free base; (S)-1-Butyl-2',6'-pipecoloxylidide; L(-)-Bupivacaine

IUPAC/Chemical Name: (S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

InChi Key: LEBVLXFERQHONN-INIZCTEOSA-N

InChi Code: InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1

SMILES Code: O=C([C@H]1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934990300


References

1: Lv BS, Wang W, Wang ZQ, Wang XW, Wang JH, Fang F, Mi WD. Efficacy and safety of local anesthetics bupivacaine, ropivacaine and levobupivacaine in combination with sufentanil in epidural anesthesia for labor and delivery: a meta-analysis. Curr Med Res Opin. 2014 Nov;30(11):2279-89. doi: 10.1185/03007995.2014.946127. Epub 2014 Aug 5. Review. PubMed PMID: 25050590.

2: Sanford M, Keating GM. Levobupivacaine: a review of its use in regional anaesthesia and pain management. Drugs. 2010 Apr 16;70(6):761-91. doi: 10.2165/11203250-000000000-00000. Review. PubMed PMID: 20394458.

3: Taya K, Shimizu S. [Levobupivacaine hydrochloride injection (POPSCAINE): pharmacological characteristics and clinical study result]. Nihon Yakurigaku Zasshi. 2009 Mar;133(3):159-67. Review. Japanese. PubMed PMID: 19282620.

4: Leone S, Di Cianni S, Casati A, Fanelli G. Pharmacology, toxicology, and clinical use of new long acting local anesthetics, ropivacaine and levobupivacaine. Acta Biomed. 2008 Aug;79(2):92-105. Review. PubMed PMID: 18788503.

5: Zink W, Graf BM. The toxicity of local anesthetics: the place of ropivacaine and levobupivacaine. Curr Opin Anaesthesiol. 2008 Oct;21(5):645-50. doi: 10.1097/ACO.0b013e32830c214c. Review. PubMed PMID: 18784493.

6: Urbanek B, Kapral S. [Levobupivacaine for regional anesthesia. A systematic review]. Anaesthesist. 2006 Mar;55(3):296-313. Review. German. PubMed PMID: 16341730.

7: Celleno D, Parpaglioni R, Frigo MG, Barbati G. Intrathecal levobupivacaine and ropivacaine for cesarean section. New perspectives. Minerva Anestesiol. 2005 Sep;71(9):521-5. Review. PubMed PMID: 16166911.

8: Casati A, Putzu M. Bupivacaine, levobupivacaine and ropivacaine: are they clinically different? Best Pract Res Clin Anaesthesiol. 2005 Jun;19(2):247-68. Review. PubMed PMID: 15966496.

9: De Cosmo G, Mascia A, Clemente A, Congedo E, Aceto P. Use of levobupivacaine for the treatment of postoperative pain after thoracotomies. Minerva Anestesiol. 2005 Jun;71(6):347-51. Review. PubMed PMID: 15886599.

10: Kuczkowski KM. Levobupivacaine and ropivacaine: the new choices for labor analgesia. Int J Clin Pract. 2004 Jun;58(6):604-5. Review. PubMed PMID: 15311561.

11: Bremerich DH, Zwissler B. [Levobupivacaine in obstetric analgesia and anaesthesia. Where is its place?]. Anaesthesist. 2004 Jul;53(7):637-44. Review. German. PubMed PMID: 15221118.

12: Capogna G, Celleno D, Camorcia M. [Levobupivacaine in obstetric analgesia and anaesthesia]. Minerva Anestesiol. 2001 Sep;67(9 Suppl 1):24-8. Review. Italian. PubMed PMID: 11778090.

13: Ivani G, Borghi B, van Oven H. Levobupivacaine. Minerva Anestesiol. 2001 Sep;67(9 Suppl 1):20-3. Review. PubMed PMID: 11778089.

14: McLeod GA, Burke D. Levobupivacaine. Anaesthesia. 2001 Apr;56(4):331-41. Review. PubMed PMID: 11284819.

15: Foster RH, Markham A. Levobupivacaine: a review of its pharmacology and use as a local anaesthetic. Drugs. 2000 Mar;59(3):551-79. Review. PubMed PMID: 10776835.

16: McClellan KJ, Spencer CM. Levobupivacaine. Drugs. 1998 Sep;56(3):355-62; discussion 363-4. Review. PubMed PMID: 9777312.