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Home> Encyclopedia >   /  Antibiotic and Antimicrobial Agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Pharmaceuticals and Biochemicals  /  Antibiotic and antimicrobial agents
Ampicillin sodium structure
Ampicillin sodium structure

Ampicillin sodium

Iupac Name:sodium;(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CAS No.:69-52-3
Molecular Weight:371.387
Introduction: A semi-synthetic broad-spectrum penicillin,it is mainly used for treatment of penicillin-sensitive gram-positive bacteria, Escherichia coli, Proteus, Salmonella, Shigella and other.
1. Names and Identifiers
1.1 Name
Ampicillin sodium
1.2 Synonyms

D-6-(-Amino-phenylacetamido)penicillanicacidsodiumsalt Domicillin omnipen-n pena/n penbritin-s penialmen polycillin-n principen/n

1.3 CAS No.
69-52-3
1.4 CID
23663979
1.5 EINECS(EC#)
200-708-1
1.6 Molecular Formula
C16H18N3NaO4S (isomer)
1.7 Inchi
InChI=1S/C16H19N3O4S.Na/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1
1.8 InChkey
KLOHDWPABZXLGI-YWUHCJSESA-M
1.9 Canonical Smiles
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)[O-])C.[Na+]
1.10 Isomers Smiles
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)[O-])C.[Na+]
2. Properties
3.1 Density
0.9450
3.2 Melting Point
215℃ (dec.)
3.3 Boiling Point
683.9 °C at 760 mmHg
3.4 Flash Point
683.9 °C at 760 mmHg
3.5 Appearance
white to off-white solid
3.6 Chemical Properties
White or almost white powder or crystal. Soluble in water, slightly soluble in ethanol, insoluble in ether. Hygroscopic, when it is set at room temperature in an aqueous solution ,it gradually turns yellow,produces turbidity, decreases potency. Odorless, slightly bitter taste.
3.7 Color/Form
white with slight yellow cast
3.8 Contact Allergens
Ampicillin caused contact dermatitis in a nurse alsosensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin)and in a pharmaceutical factoryworker. Systemic drug reactions are common. Crossreactivityis regular with ampicillin and can occur withother penicillins.
3.9 PH
pH(100g/l, 25℃):8.0~10.0
3.10 Solubility
H2O: 50?mg/mL, clear, very faintly yellow
3.11 Spectral Properties
Optical rotation = +287.9 deg at 20 deg C (C=1 in H2O)
3.12 Stability
Stable under normal temperatures and pressures.
3.13 StorageTemp
2-8°C
3.14 Water Solubility
H2O: 50 mg/mL, clear, very faintly yellow
3. Use and Manufacturing
4.1 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 204 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 204 companies. For more detailed information, please visit ECHA C&L website

Of the 9 notification(s) provided by 203 of 204 companies with hazard statement code(s):

H317 (99.01%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H334 (99.51%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501
4.2 Safety Profile
Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: hypermotility, diarrhea, and other gastrointestinal changes. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NOx, Na2O, and SOx. Ampicillin sodium Preparation Products And Raw materials Raw materials
4.3 Storage
Keep Cold.
4.4 Usage
A semi-synthetic broad-spectrum penicillin,it is mainly used for treatment of penicillin-sensitive gram-positive bacteria, Escherichia coli, Proteus, Salmonella, Shigella and other.
4. Safety and Handling
5.1 Hazard Codes
Xi
5.2 Risk Statements
R42/43
5.3 Safety Statements
S22;S36/37;S45
5.4 Hazard Note
H317; H334
5.5 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.6 Exposure Standards and Regulations
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
5.7 Formulations/Preparations
USP anhydrous ampicillin contains 900-1050 ug/mg ampicillin (calculated as the anhydrous base). Ampicillin is available in 125-, 200-, 250-, and 500-mg tablets that contain 90-120% labelled active ingredient, in 125-, 250-, and 500-mg capsules containing 90-120% labelled active ingredient, and as oral suspensions of 100, 125, and 250 mg/5 ml containing 90-120% of the labelled active ingredient and probenecid.
5.8 Safety
Hazard Codes:Xi
Risk Statements:42/43-36/37/38-22
42/43:May cause sensitization by inhalation and skin contact
36/37/38:Irritating to eyes, respiratory system and skin
22:Harmful if swallowed
Safety Statements:22-36/37-45-36-26
22:Do not breathe dust
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:2
HS Code:29419000
5.9 Specification

White powder
Safety Statements:22-36/37-45-36-26
22:Do not breathe dust
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
5.10 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XH8400000
CHEMICAL NAME :
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)- 3,3-dimethyl-7-oxo-, sodium salt, D-(-)-
CAS REGISTRY NUMBER :
69-52-3
LAST UPDATED :
199510
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C16-H18-N3-O4-S.Na
MOLECULAR WEIGHT :
371.42
WISWESSER LINE NOTATION :
T45 ANV ESTJ CMVYZR& F1 F1 GVQ &-NA-

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
100 mg/kg/5D
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,707,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5314 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 18,356,1962
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5314 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 18,356,1962
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5314 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 18,356,1962
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5314 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 18,356,1962
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2657 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 18,356,1962 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
210 mg/kg/7D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
REFERENCE :
INJPD2 Indian Journal of Pharmacology. (Dept. of Pharmacology, Baranas Hindu Univ., Varanasi 221 005, India) V.1- 1968(?)- Volume(issue)/page/year: 18,110,1986 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,153,1990 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,153,1990 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,153,1990 TOXICOLOGY REVIEW INTEAG Internist. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1960- Volume(issue)/page/year: 15,7,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3564 No. of Facilities: 549 (estimated) No. of Industries: 2 No. of Occupations: 8 No. of Employees: 23006 (estimated) No. of Female Employees: 18439 (estimated)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

Respiratory sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H317 May cause an allergic skin reaction

H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statement(s)
Prevention

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P284 [In case of inadequate ventilation] wear respiratory protection.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/...

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
product :
76497-13-7
76497-13-7
8. Computational chemical data
  • Molecular Weight:371.387g/mol
  • Molecular Formula:C16H18N3NaO4S
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:371.09157152
  • Monoisotopic Mass:371.09157152
  • Complexity:568
  • Rotatable Bond Count:4
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:6
  • Topological Polar Surface Area:141
  • Heavy Atom Count:25
  • Defined Atom Stereocenter Count:4
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:2
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