nafcillin

Modify Date: 2025-08-21 12:16:04

nafcillin structure	Common Name	nafcillin
	CAS Number	147-52-4	Molecular Weight	414.475
	Density	1.4±0.1 g/cm3	Boiling Point	714.1±60.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₂₂N₂O₅S	Melting Point	N/A
	MSDS	N/A	Flash Point	385.7±32.9 °C

Use of nafcillin

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].

Name	nafcillin
Synonym	More Synonyms

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.

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
InChIKey	GPXLMGHLHQJAGZ-JTDSTZFVSA-N
SMILES	CCOc1ccc2ccccc2c1C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O

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 3
CAS#:27605-28-3 6β-(2-phenyl-ac... CAS#:551-16-6 6-Aminopenicill... CAS#:55150-29-3 2-Ethoxynaphtha...
DownStream 0

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

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