Ampicillin

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Names

[ CAS No. ]:
69-53-4

[ Name ]:
Ampicillin

[Synonym ]:
amfipen
qidamp
ay-6108
binotal
Wymox
Unasyn
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
MFCD00072036
p-50
ab-pc
EINECS 200-709-7

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
644.5±65.0 °C at 760 mmHg

[ Melting Point ]:
198-200 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₆H₁₉N₃O₄S

[ Molecular Weight ]:
349.405

[ Flash Point ]:
343.6±34.3 °C

[ Exact Mass ]:
349.109619

[ PSA ]:
138.03000

[ LogP ]:
1.65

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.724

[ Stability ]:
Stable, but may be moisture sensitive. Incopmpatible with strong oxidizing agents.

[ Water Solubility ]:
NH4OH 1 M: 50 mg/mL, clear, colorless

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XH8350000

CHEMICAL NAME :: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3- dimethyl-7-oxo-, D-(-)-

CAS REGISTRY NUMBER :: 69-53-4

LAST UPDATED :: 199806

DATA ITEMS CITED :: 31

MOLECULAR FORMULA :: C16-H19-N3-O4-S

MOLECULAR WEIGHT :: 349.44

WISWESSER LINE NOTATION :: T45 ANV ESTJ CMVYZR& F1 F1 GVQ -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 400 mg/kg/4W-I

TOXIC EFFECTS :: Blood - agranulocytosis Blood - other changes Nutritional and Gross Metabolic - body temperature increase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 160 mg/kg/4D-I

TOXIC EFFECTS :: Blood - agranulocytosis Blood - thrombocytopenia

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4500 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6200 mg/kg

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

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

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3250 mg/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4600 mg/kg

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

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

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 380 mg/kg

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - excitement Musculoskeletal - changes in teeth and supporting structures

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

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 28 gm/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >100 mg/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 7500 ug/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2500 mg/kg

SEX/DURATION :: female 4-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 28 mg/L

REFERENCE :: HUTODJ Human Toxicology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants., RG 21 2XS, UK) V.1- 1981- Volume(issue)/page/year: 3,173,1984 *** 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 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.1 mg/m3 JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81707 No. of Facilities: 1320 (estimated) No. of Industries: 2 No. of Occupations: 4 No. of Employees: 2942 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81707 No. of Facilities: 1250 (estimated) No. of Industries: 2 No. of Occupations: 13 No. of Employees: 42346 (estimated) No. of Female Employees: 32858 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H317-H319-H334-H335

[ Precautionary Statements ]:
P261-P280-P284-P304 + P340-P305 + P351 + P338-P342 + P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R36/37/38;R42/43

[ Safety Phrases ]:
S22-S26-S36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
XH8425000

[ Packaging Group ]:
I; II; III

[ HS Code ]:
2941109200

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

6-Aminopenicillanic acid
D(-)Phenylglycinamide
methyl (R)-aminophenylacetate
(R)-4-HYDROXYMETHYL-2,2-DIMETHYL-OXAZOLIDINE-3-CARBOXYLICACIDTERT-BUTYLESTER
H-D-Phg-OMe．HCl
methyl 2-amino-2-phenylacetate hydrochloride
pivampicillin
Bacampicillin hydrochloride

DownStream

Azlocillin
6-Aminopenicillanic acid
D-2-Phenylglycine
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S,5R,6R)-
Mezlocillin
Penicillin-G
2-formyl-5,5-dimethyl-thiazolidine-4-carboxylic acid
Phenylglyoxylic acid

Customs

[ HS Code ]: 2941109200

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ampicillin
Ampicillin
Ampicillin
L-ampicillin
Ampicillin-d5
pivampicillin
ethyl 4-{3-[(2-hydroxy-4,5-dihydro-3H-1-benzazepin-3-yl)sulfanyl]propanoyl}piperazine-1-carboxylate
N-[(1-ethylpyrrolidin-2-yl)methyl]-N~3~-7H-purin-6-yl-beta-alaninamide
2-[(2-hydroxy-4,5-dihydro-3H-1-benzazepin-3-yl)sulfanyl]-N-(3-hydroxyphenyl)acetamide
1-(5-(quinoxalin-6-yl)-3-(thiophen-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
N-[1-(furan-2-yl)propan-2-yl]-2-[4-(2-oxo-2H-chromen-3-yl)phenoxy]acetamide
8-(4-Chlorophenyl)-6-(propylsulfanyl)-2,3,4,8-tetrahydropyrazolo[4,3-e]pyrimido[1,2-c]pyrimidine
1-[(4-chlorophenyl)sulfonyl]-N-[3-oxo-3-(pyrrolidin-1-yl)propyl]piperidine-3-carboxamide
2-[4-(dimethylamino)phenyl]-5-methyl-10-propyl-2,3-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione
6-chloro-N-{2-[(1,1-dioxidotetrahydrothiophen-3-yl)amino]-2-oxoethyl}-1,3,4,9-tetrahydro-2H-beta-carboline-2-carboxamide
N-[2-(furan-2-yl)ethyl]-3-[(2-hydroxy-4,5-dihydro-3H-1-benzazepin-3-yl)sulfanyl]propanamide

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