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4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

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Name

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

EINECS 200-505-8
CAS No. 61-32-5 Density 1.44 g/cm3
PSA 130.47000 LogP 1.27790
Solubility N/A Melting Point N/A
Formula C17H20N2O6S Boiling Point 640 °C at 760 mmHg
Molecular Weight 380.422 Flash Point 340.9 °C
Transport Information N/A Appearance N/A
Safety Risk Codes 22
Molecular Structure Molecular Structure of 61-32-5 (methicillin) Hazard Symbols HarmfulXn
Synonyms

6-(2,6-Dimethoxybenzamido)penicillanic acid;Penicillin, (2,6-dimethoxyphenyl)-;[2S-(2a,5a,6b)]-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid;Methicillinum;Meticilline;(2,6-Dimethoxyphenyl)penicillin;

Article Data 3

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- Synthetic route

1025-55-4

6-aminopenicillanic acid trimethylsilyl ester

1466-76-8

2-6-dimethoxybenzoic acid

61-32-5

methicillin

Conditions
ConditionsYield
(i) ClCO2Et, Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/; Multistep reaction;
551-16-6

6-Aminopenicillanic Acid

61-32-5

methicillin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3
2: (i) ClCO2Et, Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/
View Scheme
100-37-8

2-(Diethylamino)ethanol

61-32-5

methicillin

1032651-43-6

6-(2,6-dimethoxybenzamido)penicillinic acid 2-diethylaminoethyl ester hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(Diethylamino)ethanol; methicillin With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 10h;
Stage #2: With hydrogenchloride In diethyl ether; chloroform
77.5%
67-56-1

methanol

61-32-5

methicillin

22668-52-6

methicillin methyl ester

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane
61-32-5

methicillin

51579-21-6

2-(2,6-dimethoxybenzamido)acetic acid

Conditions
ConditionsYield
With water
61-32-5

methicillin

76350-41-9

6β-(2,6-dimethoxy-benzoylamino)-1,1-dioxo-1λ6-penicillanic acid

Conditions
ConditionsYield
With potassium permanganate; phosphoric acid

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- Specification

The 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-, with the CAS registry number 61-32-5, is also known as 6-(2,6-Dimethoxybenzamido)penicillanic acid. Its EINECS number is 200-505-8. This chemical's molecular formula is C17H20N2O6S and molecular weight is 380.42. What's more, its IUPAC name is (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. Its classification codes are: Anti-Bacterial Agents, Anti-Infective Agents, Drug / Therapeutic Agent, Human Data, Mutation data. When you are using this chemical, please be cautious about it. It may cause damage to health. What's more, the product is harmful if swallowed.

Physical properties of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- are: (1)ACD/LogP: 1.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.78; (4)ACD/LogD (pH 7.4): -2.46; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 110.68 Å2; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 94.44 cm3; (15)Molar Volume: 262.5 cm3; (16)Polarizability: 37.44×10-24cm3; (17)Surface Tension: 67.3 dyne/cm; (18)Density: 1.44 g/cm3; (19)Flash Point: 340.9 °C; (20)Enthalpy of Vaporization: 99.32 kJ/mol; (21)Boiling Point: 640 °C at 760 mmHg; (22)Vapour Pressure: 2.94E-17 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)c1c(OC)cccc1OC)[C@H]3SC2(C)C
(2)Std. InChI: InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
(3)Std. InChIKey: RJQXTJLFIWVMTO-TYNCELHUSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 11gm/kg/32D-I (11000mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS
New England Journal of Medicine. Vol. 279, Pg. 1245, 1968.
Link to PubMed
man TDLo unreported 229mg/kg/8D-I (229mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

KIDNEY, URETER, AND BLADDER: HEMATURIA
Antimicrobial Agents and Chemotherapy Vol. -, Pg. 765, 1961.
mouse LD50 intracrebral 38340ug/kg (38.34mg/kg)   Journal of Antibiotics, Series B. Vol. 16, Pg. 40, 1963.
mouse LD50 intravenous 3720mg/kg (3720mg/kg)   Antibiotiki. Vol. 10, Pg. 629, 1965.
Link to PubMed

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