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nafcillin

Names

[ CAS No. ]:
147-52-4

[ Name ]:
nafcillin

[Synonym ]:
Propizepina
6-(2-dimethylamino-propyl)-6,11-dihydro-benzo[b]pyrido[2,3-e][1,4]diazepin-5-one
6-(2-Ethoxy-naphth-1-yl-formamino)penicillansaeure
nafcillinum [INN_la]
(2S,5R,6R)-6-({[2-(ethyloxy)naphthalen-1-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Propizepinum
(2-ethoxy-naphthalen-1-yl)-penicillin
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
[2S-(2a,5a,6b)]-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid
Naftopen
Nallpen
Propizepinum [INN-Latin]
6-(2-Ethoxy-1-naphthamido)penicillin
Propizepina [INN-Spanish]
Vagran 50 Kapseln
Propizepine
(2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Biological Activity

[Description]:

Nafcillin, an antibiotic, is a reversible inhibitor of β-lactamase. Nafcillin exhibits bactericidal activity, and can be used for the research of staphylococcal infections[1][2][3][4].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Bacterial

[In Vivo]

Nafcillin (100 mg/kg; s.c.) exhibits bactericidal activity against methicillin-susceptible Staphylococcus aureus (MSSA) and methicillin-resistant S. aureus (MRSA), with MICs of 0.5 μg/mL and 64.0 μg/mL for S. aureus strains Xen-29 and Xen-1, respectively, in mice[3].

[References]

[1]. Tan, A.K., et al. Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase. Biochem J, 1992. 281 ( Pt 1): p. 191-6.

[2]. Palmer, D.L., et al. Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics. Ann Thorac Surg, 1995. 59(3): p. 626-31.

[3]. Lawrence I. Mortin, et al. Rapid Bactericidal Activity of Daptomycin against Methicillin-Resistant and Methicillin-Susceptible Staphylococcus aureus Peritonitis in Mice as Measured with Bioluminescent Bacteria. Antimicrob Agents Chemother. 2007 May; 51(5): 1787-1794.

[4]. Sakoulas G, et al. Nafcillin enhances innate immune-mediated killing of methicillin-resistant Staphylococcus aureus. J Mol Med (Berl). 2014 Feb;92(2):139-49.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
714.1±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C21H22N2O5S

[ Molecular Weight ]:
414.475

[ Flash Point ]:
385.7±32.9 °C

[ Exact Mass ]:
414.124939

[ PSA ]:
121.24000

[ LogP ]:
3.52

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.686

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XI0120000
CHEMICAL NAME :
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3- dimethyl-7-oxo-
CAS REGISTRY NUMBER :
147-52-4
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C21-H22-N2-O5-S
MOLECULAR WEIGHT :
414.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
1050 mg/kg/1W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - interstitial nephritis
REFERENCE :
JAMAAP JAMA, Journal of the American Medical Association. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1883- Volume(issue)/page/year: 225,178,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3659 No. of Facilities: 199 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 11979 (estimated) No. of Female Employees: 9552 (estimated)

Precursor & DownStream

Precursor

DownStream

Related Compounds