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

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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Related Compounds

  • ampicillin
  • Ampicillin
  • Ampicillin
  • L-ampicillin
  • Ampicillin-d5
  • pivampicillin
  • 3-(2-(tert-Butoxy)ethoxy)-4-fluorobenzoic acid
  • 2-Bromo-6-[1-(hydroxymethyl)cyclobutyl]phenol
  • 1-[(2-chlorothiophen-3-yl)methyl]-1H-pyrazol-4-amine
  • 4-ethyl-3-(1H-imidazol-5-yl)-1-methyl-1H-pyrazol-5-amine
  • [1-(2-ethoxyethyl)-5-ethyl-1H-1,2,3-triazol-4-yl]methanol
  • (1-{Bicyclo[2.2.1]heptan-2-yl}azetidin-2-yl)methanamine
  • 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3,5-triifluorobenzene
  • 2-(3-Fluoro-5-methylphenyl)oxirane
  • N-{3-[(oxiran-2-yl)methyl]phenyl}acetamide
  • 3-(Methylsulfonyl)-3-azabicyclo[3.1.0]hexan-6-amine-hydrochloride
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