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132-98-9

Basic Information
CAS No.: 132-98-9
Name: Penicillin V potassium salt
Molecular Structure:
Molecular Structure of 132-98-9 (Penicillin V potassium salt)
Formula: C16H17KN2O5S
Molecular Weight: 388.47
Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-, potassium salt (1:1),(2S,5R,6R)-;Potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;Stabilin V-K;SK-Penicillin VK;Sumapen VK;Rocilin;Phenoxymethylpenicillin potassium salt;Potassium penicillin V salt;Potassium phenoxymethylpenicillin;Primcillin;Qidpen VK;Rafapen V-K;Robicillin VK;Ispenoral;Ledercillin Vk;Beromycin 400;Calciopen K;Fenocin;Fenoxcillin;Beromycin;P.V.O.;Pedipen;Pen-V;Pen-Vee K Powder;Oracillin VK;Penapar VK;Phenoxymethylpenicillin Potassium;
EINECS: 205-086-5
Density: 1.40 g/cm3
Melting Point: 197-202 °C
Boiling Point: 681.4 °C at 760 mmHg
Flash Point: 365.9 °C
Solubility: Soluble in water, dimethyl sulfoxide, and methanol.
Appearance: Odorless white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-42/43
Safety: 22-26-36/37-45
Transport Information:
PSA: 124.07000
LogP: -0.30880
Synthetic route

potassium 2-ethylhexanoate

87-08-1

penicilin V

132-98-9

penicillin V potassium

Conditions
ConditionsYield
In butan-1-ol80%
551-16-6

6-Aminopenicillanic Acid

701-99-5

Phenoxyacetyl chloride

132-98-9

penicillin V potassium

Conditions
ConditionsYield
Stage #1: 6-Aminopenicillanic Acid; Phenoxyacetyl chloride With sodium hydrogencarbonate In water; acetone at 10 - 15℃; for 0.333333h;
Stage #2: With potassium 2-ethylhexanoate In butan-1-ol
80%
551-16-6

6-Aminopenicillanic Acid

132-98-9

penicillin V potassium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / water; acetone / 0.35 h / 10 - 15 °C
1.2: pH 2
2.1: butan-1-ol
View Scheme
701-99-5

Phenoxyacetyl chloride

132-98-9

penicillin V potassium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / water; acetone / 0.35 h / 10 - 15 °C
1.2: pH 2
2.1: butan-1-ol
View Scheme
132-98-9

penicillin V potassium

100-11-8

1-bromomethyl-4-nitro-benzene

58244-55-6

4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl-formamide for 15h; Ambient temperature;97%
100-39-0

benzyl bromide

132-98-9

penicillin V potassium

1256-06-0

(2S,5R,6R)-benzyl-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h; Ambient temperature;95%
In N,N-dimethyl-formamide Ambient temperature;

C56H135ClN4Si7(4+)*4I(1-)

132-98-9

penicillin V potassium

C72H152N6O5SSi7(4+)*4I(1-)

Conditions
ConditionsYield
With 18-crown-6 ether; sodium iodide In N,N-dimethyl-formamide at 100℃; for 40h; Inert atmosphere; Sealed tube;95%
132-98-9

penicillin V potassium

74-88-4

methyl iodide

2315-05-1

methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 17h;94%
In N,N-dimethyl-formamide at 20℃; for 1h;65%
In N,N-dimethyl-formamide at 20℃; for 12h;63%
625-56-9

Chloromethyl acetate

132-98-9

penicillin V potassium

72842-44-5

acetoxymethyl 6-(phenoxyacetamido)-penicillinate

Conditions
ConditionsYield
In dimethyl sulfoxide for 20h; Ambient temperature;92%

C26H63ClN2Si3(2+)*2I(1-)

132-98-9

penicillin V potassium

C42H80N4O5SSi3(2+)*2I(1-)

Conditions
ConditionsYield
With 18-crown-6 ether; sodium iodide In N,N-dimethyl-formamide at 80℃; for 40h; Inert atmosphere; Sealed tube;89%
132-98-9

penicillin V potassium

5,11,17,23-tetra(tert-butyl)-25,27-bis-(3-hydroxypropoxy)-26,28-bis-hydroxycalix[4]arene

C82H100N4O14S2

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 42h; Inert atmosphere;32%
132-98-9

penicillin V potassium

15583-33-2

(3S,5R,6R)-3-diazoacetyl-2,2-dimethyl-6-phenoxyacetamidopenam

Conditions
ConditionsYield
(i) SOCl2, CHCl3, (ii) /BRN= 102415/; Multistep reaction;
With chloroformic acid ethyl ester; triethylamine hydrochloride 1.) CH2Cl2, (CCl4-solid CO2), 1.25 h, 2.) Et2O, 0 deg C, 1.5 h; Yield given. Multistep reaction;
577-56-0

2-acetyl-benzoic acid

132-98-9

penicillin V potassium

55361-58-5

6β-(2-phenoxy-acetylamino)-penicillanic acid (Ξ)-1-methyl-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester

Conditions
ConditionsYield
(i) Py, PhSO2Cl, (ii) /BRN= 3899450/; Multistep reaction;
6940-49-4

3-Bromophthalide

132-98-9

penicillin V potassium

60158-36-3

6β-(2-phenoxy-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide
109-79-5

1-butanethiol

132-98-9

penicillin V potassium

69577-99-7

(5R)-3,3-dimethyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carbothioic acid S-butyl ester

Conditions
ConditionsYield
With potassium carbonate In 1,2-dimethoxyethane Ambient temperature;
542-81-4

sulfure de methyle et de 2-chloroethyle

132-98-9

penicillin V potassium

66260-34-2

6β-(2-phenoxy-acetylamino)-penicillanic acid 2-methylsulfanyl-ethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide
132-98-9

penicillin V potassium

(5R)-3,3-dimethyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carbothioic acid

Conditions
ConditionsYield
(i) Et3N*HCl, CH2Cl2, (ii) ClCO2Et, DMF, (iii) NaSH; Multistep reaction;
132-98-9

penicillin V potassium

108-98-5

thiophenol

69577-98-6

(5R)-3,3-dimethyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carbothioic acid S-phenyl ester

Conditions
ConditionsYield
With potassium carbonate In 1,2-dimethoxyethane Ambient temperature;
132-98-9

penicillin V potassium

75-08-1

ethanethiol

69577-97-5

(5R)-3,3-dimethyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carbothioic acid S-ethyl ester

Conditions
ConditionsYield
With potassium carbonate In 1,2-dimethoxyethane Ambient temperature;
10477-40-4

1-chloroethyl phenyl ether

132-98-9

penicillin V potassium

penicillin V, 1-(phenoxy)ethyl ester

Conditions
ConditionsYield
at 0℃; Yield given;
85721-33-1

ciprofloxacin

132-98-9

penicillin V potassium

1-Cyclopropyl-7-{4-[(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-piperazin-1-yl}-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
With chloroformic acid ethyl ester; 4-methyl-morpholine 1.) CH2Cl2, -7 to -10 deg C, 45 min, 2.) CH2Cl2, MeOH, -5 to 0 deg C, 2 h; Yield given. Multistep reaction;
132-98-9

penicillin V potassium

20455-68-9

N,N-dibenzylamine hydrochloride

121527-61-5

penicillin V dibenzylamine salt

Conditions
ConditionsYield
With potassium phenoxyacetate In water at 5℃;692 mg
132-98-9

penicillin V potassium

A

87796-73-4

(R)-3-Methyl-2-[(S)-2-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid

B

87796-74-5

(R)-α-[(S)-2-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-isovaleric acid

Conditions
ConditionsYield
With nickel In water at 165℃; for 0.25h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With nickel In water at 165℃; for 0.25h; Yield given. Yields of byproduct given;
132-98-9

penicillin V potassium

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

7-{4-[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-piperazin-1-yl}-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
With chloroformic acid ethyl ester; 4-methyl-morpholine 1.) CH2Cl2, -7 to -10 deg C, 45 min, 2.) CH2Cl2, MeOH, -5 to 0 deg C, 2 h; Yield given. Multistep reaction;
132-98-9

penicillin V potassium

78-95-5

chloroacetone

72881-16-4

(2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-oxo-propyl ester

Conditions
ConditionsYield
With sodium periodate Yield given. Multistep reaction;
Downstream Products
2315-05-1
52-67-5
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Consensus Reports

NTP Carcinogenesis Studies (gavage): No Evidence: Mouse, Rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-336 ,1988. . Reported in EPA TSCA Inventory.

Specification

The Penicillin V potassium salt, with the CAS registry number 132-98-9, is also known as Xanthylium,9-(2,4-disulfophenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, inner salt, sodiumsalt (1:1). It belongs to the product categories of Peptide Synthesis/Antibiotics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds. Its EINECS number is 205-086-5. This chemical's molecular formula is C16H17KN2O5S and molecular weight is 388.47. What's more, its systematic name is Potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate. Its classification codes are: (1)Antibacterial; (2)Drug / Therapeutic Agent; (3)Mutation data; (4)Tumor data. This chemical is a broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms. It is used in biochemical research. It should be sealed and stored in a cool and dry place.

Physical properties of Penicillin V potassium salt are: (1)ACD/LogP: 1.875; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.10; (4)ACD/LogD (pH 7.4): -1.85; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 112.45 Å2; (13)Flash Point: 365.9 °C; (14)Enthalpy of Vaporization: 105 kJ/mol; (15)Boiling Point: 681.4 °C at 760 mmHg; (16)Vapour Pressure: 1.69E-19 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It may cause sensitisation by inhalation and skin contact. You should not breathe dust. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: [K+].O=C([O-])[C@@H]2N3C(=O)[C@@H](NC(=O)COc1ccccc1)[C@H]3SC2(C)C
(2)Std. InChI: InChI=1S/C16H18N2O5S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
(3)Std. InChIKey: HCTVWSOKIJULET-LQDWTQKMSA-M

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1351mg/kg (1351mg/kg)   Drugs in Japan Vol. 6, Pg. 661, 1982.
mouse LD50 intravenous 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 751, 1962.
mouse LD50 oral > 4gm/kg (4000mg/kg)   Drugs in Japan Vol. 6, Pg. 661, 1982.
mouse LD50 subcutaneous > 4gm/kg (4000mg/kg)   Drugs in Japan Vol. 6, Pg. 661, 1982.
rat LD50 intramuscular 1124mg/kg (1124mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 29, Pg. 39, 1977.
rat LD50 intraperitoneal 1750mg/kg (1750mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 751, 1962.
rat LD50 oral > 1040mg/kg (1040mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.