Bupivacaine hydrochloride

Iupac Name：1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride

Molecular Weight：324.893

Modify Date.: 2022-10-31 04:29

Introduction: Sodium channel blocker, local anestheticBupivacaine hydrochloride is an amide-type local anesthetic, generally used for nerve block anesthesia, local infiltration anesthesia and epidural anesthesia. Its mechanism of action is similar to that of amide-type local anesthetics, that is, the drug is first combined with plasma proteins, metabolized by the liver, and then excreted from the urine through the kidneys. View more+

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1. Names and Identifiers

1.1 Name: Bupivacaine hydrochloride
1.2 Synonyms: Bupivacaine hydrochloride 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride BUPIVACAINE HYDROCHLORIDE CAS NO.14252-80-3 Bupivacaine Hydrochloride, USP IN STOCK BUPIVACAINE HYDROCHLORIDE CAS NO.14252-80-3 Local Anesthetic Pharmaceutical Raw Material Bupivacaine HCl CAS 14252-80-3

1.3 CAS No.: 14252-80-3

1.4 CID: 64737

1.5 EINECS(EC#): 241-917-8

1.6 Molecular Formula: C18H29ClN2O (isomer)

1.7 Inchi: InChI=1S/C18H28N2O.ClH/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);1H

1.8 InChkey: SIEYLFHKZGLBNX-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl

1.10 Isomers Smiles: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl

2. Properties

2.1 Melting point: 249-251 °C

2.1 Boiling point: 423.4 °C at 760 mmHg

2.1 Flash Point: 209.9 °C

2.1 Precise Quality: 324.19700

2.1 PSA: 32.34000

2.1 logP: 4.70940

2.1 Appearance: white solid

2.2 Chemical Properties: White Solid

2.3 Water Solubility: soluble

2.4 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 Usage: antineoplastic

4. Safety and Handling

4.1 Hazard Codes: T+

4.1 Risk Statements: R26/27/28

4.1 Safety Statements: S22;S36/37/39;S45

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including bupivacane hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Bupivacane hydrochloride/

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow = 3.41

4.3 Other Preventative Measures: Airborne exposure should be controlled primarily by engineering controls such as general dilution ventilation, local exhaust ventilation, or process enclosure. Local exhaust ventilation is generally preferred to general exhaust because it can control the contaminant at its source, preventing dispersion into the work area. An industrial hygiene survey involving air monitoring may be used to determine the effectiveness of engineering controls. Effectiveness of engineering controls intended for use with highly potent materials should be assessed by use of nontoxic surrogate materials Local exhaust ventilation such as a laboratory fume hood or other vented enclosure is recommended, particularly for grinding, crushing weighing, or other dust-generating procedures. /Bupivacaine hydrochloride/
As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Clean equipment and work surfaces with suitable detergent or solvent after use. After removing gloves, wash hands and other exposed skin thoroughly. /Bupivacaine hydrochloride/
For handling solutions, ensure that the glove material is protective against the solvent being used. Use handling practices that minimize direct hand contact. Employees who are sensitive to natural rubber (latex) should use nitrile or other synthetic nonlatex gloves. Use of powdered latex gloves should be avoided due to the risk of latex allergy. /Bupivacaine hydrochloride/
Maintain eyewash facilities in the work area. /Bupivacaine hydrochloride/
SRP: Contaminated protective clothing should be segregated in a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

4.4 Hazard Class: 6.1(b)

4.4 Cleanup Methods: Wear approved respiratory protection, chemically compatible gloves, and protective clothing. Wipe up spillage or collect spillage in appropriately labeled container for disposal. Wash spill site. /Bupivacaine hydrochloride/

4.5 DisposalMethods: SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

4.6 RIDADR: UN 2811

4.6 Fire Fighting Procedures: As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing. /Bupivacaine hydrochloride/
Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials. /Bupivacaine hydrochloride/

4.7 FirePotential: This material is assumed to be combustible. /Bupivacaine hydrochloride/

4.8 Formulations/Preparations: Bupivacaine Hydrochloride Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Parenteral Injection 0.25% Bupivacaine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.25% Marcaine Hydrochloride (Hospira) Parenteral Injection 0.25% Sensorcaine (AstraZeneca) Parenteral Injection 0.5% Bupivacaine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.5% Marcaine Hydrochloride (Hospira) Parenteral Injection 0.5% Sensorcaine (AstraZeneca) Parenteral Injection 0.75% Bupivacaine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.75% Marcaine-MPF Hydrochloride (Sanofi) Parenteral Injection 0.75% Sensorcaine-MPF (Astra-Zeneca)
Bupivacaine Hydrochloride in Dextrose Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Parenteral Injection 0.75% in 8.25% Dextrose Bupivacaine Spinal (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.75% in 8.25% Dextrose Marcaine Spinal (Hospira) Parenteral Injection 0.75% in 8.25% Dextrose Sensorcaine-MPF Spinal (AstraZeneca)

4.9 WGK Germany: 3

4.9 RTECS: TK6125000

4.9 Protective Equipment and Clothing: Safety glasses with sideshields are recommended. Face shields or goggles may be required if splash potential exists or if corrosive materials are present. Approved eye protection (eg, bearing the ANSI Z87 or CSA stamp) is preferred. /Bupivacaine hydrochloride/
Where respirators are deemed necessary to reduce or control occupational exposures, use NIOSH-approved respiratory protection and have an effective respirator program in place. /Bupivacaine hydrochloride/
For handling of laboratory scale quantities, a cloth lab coat is recommended. Where significant quantities are handled, work clothing may be necessary to prevent take-home contamination. /Bupivacaine hydrochloride/

4.10 Skin, Eye, and Respiratory Irritations: Possible eye, skin, ... and/or respiratory tract irritation. /Bupivacaine hydrochloride/

4.11 Safety: Hazard Codes:?T+
Risk Statements: 26/27/28?
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39-45?
S22:Do not breathe dust.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: TK6125000
HazardClass: 6.1(b)
PackingGroup: III

4.12 Specification: ?Bupivacaine hydrochloride , its cas register number is 14252-80-3. It also can be called Bupivacaine hydrochloride [USAN] ; (+-)-1-Butyl-2',6'-pipecoloxylidide monohydrochloride,monohydrate ; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, monohydrate ; Bupicacain hydrochlorid-1-wasser ; Bupivacaine ; Bupivacaine hydrochloride preservative free ; Marcaine hydrochloride ; Marcaine hydrochloride preservative free ; Marcaine spinal ; Sensorcaine .It is a?white solid.

4.13 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TK6125000

CHEMICAL NAME :: 2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride, (+-)-

CAS REGISTRY NUMBER :: 14252-80-3

LAST UPDATED :: 199707

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C18-H28-N2-O.Cl-H

MOLECULAR WEIGHT :: 324.94

WISWESSER LINE NOTATION :: T6NTJ A4 BVMR B1 F1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 43 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 58700 ug/kg

TOXIC EFFECTS :: Behavioral - anticonvulsant Behavioral - somnolence (general depressed activity)

REFERENCE :: AACRAT Anesthesia and Analgesia (New York). (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.36- 1957- Volume(issue)/page/year: 60,385,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 59 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ANPRBG Anesthesia Progress. (Elsevier Science Publishing Co.,Inc., 655 Avenue of the Americas, New York, NY 10010) V.13- 1966- Volume(issue)/page/year: 36,79,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 22753 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DDREDK Drug Development Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 21,277,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 18 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 48 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 11 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,680,1982

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 2

Acute toxicity - Dermal, Category 2

Acute toxicity - Inhalation, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H300 Fatal if swallowed H310 Fatal in contact with skin H330 Fatal if inhaled
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P262 Do not get in eyes, on skin, or on clothing. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P310 Immediately call a POISON CENTER/doctor/\u2026 P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P320 Specific treatment is urgent (see ... on this label).
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

14252-80-3Total: 3 Synthesis Route

109-65-9 243 Suppliers

14252-80-3 282 Suppliers

Literatures:
Acta Chemica Scandinavica (1947-1973), , vol. 11, p. 1183,1184
Yield: null

27262-45-9 9 Suppliers

14252-80-3 282 Suppliers

Literatures:
Langston, Marianne; Dyer, Ulrich C.; Frampton, Graham A.C.; Hutton, Gordon; Lock, Christopher J.; Skead, Benjamin M.; Woods, Martin; Zavareh, Hooshang S. Organic Process Research and Development, 2000 , vol. 4, # 6 p. 530 - 533
Yield: ~97%

14252-80-3 282 Suppliers

Literatures:
BRIDGE PHARMA, INC. Patent: WO2008/88756 A1, 2008 ; Location in patent: Page/Page column 30-31 ;
Yield: ~94%

8. Precursor and Product

precursor:

109-65-9

27262-45-9

14252-80-3

product :

14252-80-3

9. Other Information

9.0 Chemical Properties: White Solid

9.1 Uses: antineoplastic

9.2 Uses: Sodium channel blocker, local anesthetic

9.3 Brand name: Marcaine (Hospira); Sensorcaine (AstraZeneca).

10. Computational chemical data

Molecular Weight: 324.893g/mol
Molecular Formula: C₁₈H₂₉ClN₂O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 324.1968412
Monoisotopic Mass: 324.1968412
Complexity: 321
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 32.3
Heavy Atom Count: 22
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7IAAEAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAAABAAAAHgAQAAAADCjBmAQywIPAAACIAiVSUACCAAAhAAAIiAGIRIgIYDLAkbGUIAhglADIyAcYiEAOAAACAAACAAAAAAQAAAQAAAAAAAAAAA==

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