 Home > Encyclopedia > 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)-

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)-

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)- structure

CAS No:
4697-14-7
Formula:
C15H16N2O6S2.2Na
Chemical Name:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)-
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-,sodium salt (1:2),(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(carboxy-3-thienylacetyl)amino]-3,3-dimethyl-7-oxo-,disodium salt,[2S-(2α,5α,6β)]-;3-Thiophenemalonamic acid,N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-,disodium salt;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(carboxy-3-thienylacetyl)amino]-3,3-dimethyl-7-oxo-,disodium salt,(2S,5R,6R)-;Ticillin;Aerugipen;41459-08-9
Categories:
Active Pharmaceutical Ingredients > Antibiotics

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Description

Ticarcillin disodium is an injectable antibiotic for the treatment of Gram-negative bacteria, particularly Pseudomonas aeruginosa. It is also one of the few antibiotics capable of treating Stenotrophomonas maltophilia infections.

An antibiotic derived from penicillin similar to CARBENICILLIN in action.

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)- Basic Attributes

Molecular Weight：

428.39

Exact Mass：

428.008881

EC Number：

249-642-5

DSSTox ID：

DTXSID8045561

Characteristics

PSA：

183.21000

XLogP3：

-1.79260

Appearance：

white to light yellow

Boiling Point：

768.3ºC at 760 mmHg

Flash Point：

418.4ºC

Water Solubility：

H2O: soluble 50mg/mL

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-42-43-42/43

safety instructions：

26-36/37

RTECS Number：

XM9410000

Marks：

Xn,Xi

Precautionary statement(s)：

P261-P305 + P351 + P338-P342 + P311

Hazard Statements：

H315-H319-H334-H335

GHS Classification：

|Danger|H315 (93.18%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 44 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

BRL 2288

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)- Use and Manufacturing

Methods of Manufacturing

Method 1: 1.38g (5mm01) (thiophen-3-yl) malonate monobenzyl ester (I) and 2.5ml of dichlorosulfoxide, heated at 50～55℃ for 1h, and then heated at 60～65℃ for 10min . Under reduced pressure and below 30°C, the excess dichlorosulfoxide is removed, and finally 1 ml of benzene can be added, and the trace amount of dichlorosulfoxide is removed by azeotropy under high vacuum, and the rest is yellow oily (thiophene -3-yl) malonic acid monobenzyl ester chloride (II). The acid chloride (II) was dissolved in 10 ml of dry acetone, and on the stirring and steam bath, a mixed solution of 1.08 g (5 mmo1) 6-APA, 15 m11 mol/L sodium bicarbonate and 5 ml of acetone was added. When the reaction started, the reaction solution was stirred at room temperature for 45 min. After the reaction solution was washed with diethyl ether (3×25m1), it was acidified with about 11 m11mol/L hydrochloric acid to Ph=2, and then the acidic aqueous solution was extracted with diethyl ether (3×15m1). The extract was decolorized with activated carbon and magnesium sulfate together for 5 min. Filter, shake the light yellow filtrate and about 4m11mol/L sodium bicarbonate to obtain a water-soluble extract with Ph value of 7-7.5. After the water-soluble extract is concentrated at low temperature and low pressure, isopropyl alcohol is added to the residue and stirred together until the mixture contains 10% water. At this time, crystallization started, and it was left overnight at 0°C to complete the crystallization. White crystals of α-(benzyloxycarbonyl)-3-thienylmethylpenicillin sodium (Ⅲ) were obtained in a yield of 50%. 10.65g of 5% calcium carbonate-supported palladium catalyst was suspended in 32ml of water, hydrogenated in advance for 1h, then 2.13g (4.3mmo1) of the sodium salt (III) obtained above was dissolved in 30ml of water, at a pressure slightly above atmospheric pressure Under hydrogenation for 1.5h. Filtration is carried out with a device equipped with Dicalite (a kind of diatomaceous earth). The clear filtrate was concentrated at low temperature and low pressure, and the residue was dried in vacuum in the presence of phosphorus pentoxide to obtain ticarcillin sodium as a white solid. Method 2: 2-thiophene-2-benzyloxycarbonylacetyl chloride (II) acylates the benzyl ester of 6-APA to obtain compound (IV), and then hydrogenolysis to remove two benzyl protecting groups, and then use sodium bicarbonate After neutralization, ticarcillin sodium can be obtained.

Uses

coccidiostat

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:428.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:3
Exact Mass:428.00886708
Monoisotopic Mass:428.00886708
Topological Polar Surface Area:183
Heavy Atom Count:27
Complexity:629
Undefined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes

Material

Thionyl chloride

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Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
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4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)-

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